Electron-Rich Phosphines in Organic Synthesis II. Catalytic Applications

Synthesis

Volumn , Issue 16, 2003, Pages 2437-2460

  Valentine Jr , Donald H ^a   Hillhouse, John H ^b  

^a Cytec Canada Inc ^*  (United States)

^b Cytec Canada Inc   (Canada)

Author keywords

Carbonylations; Catalysis; Heck reaction; Hydroformylations; Ligands

Indexed keywords

HYDROFORMYLATIONS; LIGAND CATALYZED REACTIONS;

CATALYSIS; ELECTRONS; HYDROGENATION; POLYMERIZATION; RUTHENIUM; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; RUTHENIUM;

ARYLATION; CARBONYLATION; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ELECTRON; HECK REACTION; HYDROFORMYLATION; HYDROGENATION; POLYMERIZATION; REVIEW; SYNTHESIS;

EID: 0345305280     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

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157. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
158. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
159. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
160. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
161. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
162. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
163. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
164. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
165. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
166. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
167. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
168. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
169. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
170. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
171. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all
172. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
173. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
174. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
175. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
176. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
177. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
178. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
179. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
180. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
181. Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly. (a) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. (b) Heck reaction: Littke, A. F.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989. (c) Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123. (d) Suzuki reaction: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (e) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (f) Suzuki reaction: Monteith, M. WO 98 16486, 1998; Chem. Abstr. 1998, 128, 294592. (g) Suzuki reaction: Cornils, B. Proc. Res. Dev. 1998, 2, 121. (h) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (i) Sonagashira reaction: Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (j) Diaryl ether formation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (k) Amination: Hartwig, J. F. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41, 420. (l) Amination: Hartwig, J. F.; Goodson, F. E.; Louie, J.; Hauck, S. Polym. Mater. Sci. Eng. 1999, 80, 41. (m) Amination: Lin, S. L.; Zhou, W.; Matcham, G. W. Celgro US 6,107,521, 2000; Chem. Abstr. 2000, 133, 179296. (n) Amination: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (o) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (p) Amination: Yamamoto, T.; Nishiyama, M.; Koie, Y. Toso Kenkyu Hokoku 1997, 41, 49; Chem. Abstr. 1998, 128, 180180. (q) Amination: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (r) Amination: Watanabe, M.; Yamamoto, T.; Nishiyama, M. Angew. Chem. Int. Ed. 2000, 39, 2501. (s) Amination: Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527. (t) Amination: Braig, T.; Muller, D. C.; Gross, M.; Meerholz, K.; Nuyken, O. Macromol. Rapid Commun. 2000, 21, 583. (u) Negishi cross coupling: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719. (v) Arylation of ketones malonates etc.: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473. (w) Arylation of ketones malonates etc.: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I. U.S. 6,100,398, 2000; Chem. Abstr. 2000, 131, 310548. (x) Heterocyclic substitution: Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2000, 66, 9067.
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