Highly active palladium catalysts supported by bulky proazaphosphatrane ligands for stille cross-coupling: Coupling of aryl and vinyl chlorides, room temperature coupling of aryl bromides, coupling of aryl triflates, and synthesis of sterically hindered biaryls

Journal of the American Chemical Society

Volumn 126, Issue 50, 2004, Pages 16433-16439

  Su, Weiping ^a   Urgaonkar, Sameer ^a   McLaughlin, Patrick A ^a   Verkade, John G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; CATALYSTS; POLYVINYL CHLORIDES;

CATALYST SYSTEMS; PROAZOPHOSPHATRANE LIGANDS; STILLE COUPLING; STILLE REACTIONS;

PALLADIUM;

ALKANE DERIVATIVE; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; LIGAND; ORGANOTIN COMPOUND; PALLADIUM COMPLEX; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYST; CROSS COUPLING REACTION; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 11444254369     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0450096     Document Type: Article

References (67)

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6. For reviews of the Stille reaction, see: (a) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (c) Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterwoth: London, 1987. (d) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (e) Hassa, J.; Svignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (f) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
7. For reviews of the Stille reaction, see: (a) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (c) Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterwoth: London, 1987. (d) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (e) Hassa, J.; Svignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (f) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
8. For reviews of the Stille reaction, see: (a) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (c) Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterwoth: London, 1987. (d) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (e) Hassa, J.; Svignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (f) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
9. For reviews of the Stille reaction, see: (a) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (c) Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterwoth: London, 1987. (d) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (e) Hassa, J.; Svignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (f) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
10. For recent applications of the Stille reaction in natural product synthesis, see (a) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupali, P.; Mitchell, H. J.; Fylaktakidou, K. C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A. J. Am. Chem. Soc. 2003, 125, 15443. (b) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46. (c) Lin, S.-Y.; Chen, C.-L.; Lee, Y.-J. J. Org. Chem. 2003, 68, 2968. (d) Boger, D. L.; Ichikawa, S.; Jing, H. J. Am. Chem. Soc. 2000, 122, 12169. (e) Jensen, M. S.; Yang, C.; Hsiao, Y.; Rivera, N.; Wells, K. M.; Chung, J. Y. L.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2000, 2, 1081.
11. For recent applications of the Stille reaction in natural product synthesis, see (a) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupali, P.; Mitchell, H. J.; Fylaktakidou, K. C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A. J. Am. Chem. Soc. 2003, 125, 15443. (b) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46. (c) Lin, S.-Y.; Chen, C.-L.; Lee, Y.-J. J. Org. Chem. 2003, 68, 2968. (d) Boger, D. L.; Ichikawa, S.; Jing, H. J. Am. Chem. Soc. 2000, 122, 12169. (e) Jensen, M. S.; Yang, C.; Hsiao, Y.; Rivera, N.; Wells, K. M.; Chung, J. Y. L.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2000, 2, 1081.
12. For recent applications of the Stille reaction in natural product synthesis, see (a) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupali, P.; Mitchell, H. J.; Fylaktakidou, K. C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A. J. Am. Chem. Soc. 2003, 125, 15443. (b) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46. (c) Lin, S.-Y.; Chen, C.-L.; Lee, Y.-J. J. Org. Chem. 2003, 68, 2968. (d) Boger, D. L.; Ichikawa, S.; Jing, H. J. Am. Chem. Soc. 2000, 122, 12169. (e) Jensen, M. S.; Yang, C.; Hsiao, Y.; Rivera, N.; Wells, K. M.; Chung, J. Y. L.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2000, 2, 1081.
13. For recent applications of the Stille reaction in natural product synthesis, see (a) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupali, P.; Mitchell, H. J.; Fylaktakidou, K. C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A. J. Am. Chem. Soc. 2003, 125, 15443. (b) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46. (c) Lin, S.-Y.; Chen, C.-L.; Lee, Y.-J. J. Org. Chem. 2003, 68, 2968. (d) Boger, D. L.; Ichikawa, S.; Jing, H. J. Am. Chem. Soc. 2000, 122, 12169. (e) Jensen, M. S.; Yang, C.; Hsiao, Y.; Rivera, N.; Wells, K. M.; Chung, J. Y. L.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2000, 2, 1081.
14. For recent applications of the Stille reaction in natural product synthesis, see (a) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupali, P.; Mitchell, H. J.; Fylaktakidou, K. C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A. J. Am. Chem. Soc. 2003, 125, 15443. (b) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 46. (c) Lin, S.-Y.; Chen, C.-L.; Lee, Y.-J. J. Org. Chem. 2003, 68, 2968. (d) Boger, D. L.; Ichikawa, S.; Jing, H. J. Am. Chem. Soc. 2000, 122, 12169. (e) Jensen, M. S.; Yang, C.; Hsiao, Y.; Rivera, N.; Wells, K. M.; Chung, J. Y. L.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2000, 2, 1081.
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17. For leading references to Suzuki couplings of aryl chlorides, see (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722; (b) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (d) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540. (e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (h) Urgaonkar, S. Nagarajan, M. Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
18. For leading references to Suzuki couplings of aryl chlorides, see (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722; (b) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (d) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540. (e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (h) Urgaonkar, S. Nagarajan, M. Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
19. For leading references to Suzuki couplings of aryl chlorides, see (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722; (b) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (d) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540. (e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (h) Urgaonkar, S. Nagarajan, M. Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
20. For leading references to Suzuki couplings of aryl chlorides, see (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722; (b) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (d) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540. (e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (h) Urgaonkar, S. Nagarajan, M. Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
21. For leading references to Suzuki couplings of aryl chlorides, see (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722; (b) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (d) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540. (e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (h) Urgaonkar, S. Nagarajan, M. Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
22. For leading references to Suzuki couplings of aryl chlorides, see (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722; (b) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (d) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540. (e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (h) Urgaonkar, S. Nagarajan, M. Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
23. For leading references to Suzuki couplings of aryl chlorides, see (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722; (b) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (d) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540. (e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (h) Urgaonkar, S. Nagarajan, M. Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
24. For leading references to Suzuki couplings of aryl chlorides, see (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722; (b) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. Engl. 1998, 37, 3387. (c) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020. (d) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540. (e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (h) Urgaonkar, S. Nagarajan, M. Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
25. For leading references to Heck reactions of aryl chlorides, see (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989. (b) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031. (c) Schnyder, A.; Aemmer, T.; Indolese, A. F.; Pittelkow, U.; Studer, M. Adv. Synth. Catal. 2002, 344, 495. (d) Proeckl, S. S.; Kleist, W.; Gruber, M. A.; Koehler, K. Angew. Chem., Int. Ed. 2004, 43, 1881.
26. For leading references to Heck reactions of aryl chlorides, see (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989. (b) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031. (c) Schnyder, A.; Aemmer, T.; Indolese, A. F.; Pittelkow, U.; Studer, M. Adv. Synth. Catal. 2002, 344, 495. (d) Proeckl, S. S.; Kleist, W.; Gruber, M. A.; Koehler, K. Angew. Chem., Int. Ed. 2004, 43, 1881.
27. For leading references to Heck reactions of aryl chlorides, see (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989. (b) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031. (c) Schnyder, A.; Aemmer, T.; Indolese, A. F.; Pittelkow, U.; Studer, M. Adv. Synth. Catal. 2002, 344, 495. (d) Proeckl, S. S.; Kleist, W.; Gruber, M. A.; Koehler, K. Angew. Chem., Int. Ed. 2004, 43, 1881.
28. For leading references to Heck reactions of aryl chlorides, see (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989. (b) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031. (c) Schnyder, A.; Aemmer, T.; Indolese, A. F.; Pittelkow, U.; Studer, M. Adv. Synth. Catal. 2002, 344, 495. (d) Proeckl, S. S.; Kleist, W.; Gruber, M. A.; Koehler, K. Angew. Chem., Int. Ed. 2004, 43, 1881.
29. For leading references to Buchwald-Hartwig amination reactions of aryl chlorides, see: (a) Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307. (d) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (e) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (g) Reddy, N. P.; Tanaka, M.; Tetrahedron Lett. 1997, 38, 4807. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
30. For leading references to Buchwald-Hartwig amination reactions of aryl chlorides, see: (a) Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307. (d) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (e) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (g) Reddy, N. P.; Tanaka, M.; Tetrahedron Lett. 1997, 38, 4807. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
31. For leading references to Buchwald-Hartwig amination reactions of aryl chlorides, see: (a) Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307. (d) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (e) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (g) Reddy, N. P.; Tanaka, M.; Tetrahedron Lett. 1997, 38, 4807. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
32. For leading references to Buchwald-Hartwig amination reactions of aryl chlorides, see: (a) Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307. (d) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (e) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (g) Reddy, N. P.; Tanaka, M.; Tetrahedron Lett. 1997, 38, 4807. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
33. For leading references to Buchwald-Hartwig amination reactions of aryl chlorides, see: (a) Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307. (d) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (e) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (g) Reddy, N. P.; Tanaka, M.; Tetrahedron Lett. 1997, 38, 4807. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
34. For leading references to Buchwald-Hartwig amination reactions of aryl chlorides, see: (a) Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307. (d) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (e) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (g) Reddy, N. P.; Tanaka, M.; Tetrahedron Lett. 1997, 38, 4807. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
35. For leading references to Buchwald-Hartwig amination reactions of aryl chlorides, see: (a) Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307. (d) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (e) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (g) Reddy, N. P.; Tanaka, M.; Tetrahedron Lett. 1997, 38, 4807. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
36. For leading references to Buchwald-Hartwig amination reactions of aryl chlorides, see: (a) Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307. (d) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. (e) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (g) Reddy, N. P.; Tanaka, M.; Tetrahedron Lett. 1997, 38, 4807. (h) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
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56. Nakatsu, K.; Kinoshita, K.; Kanda, H.; Isobe, K.; Nakamura, Y.; Kawaguchi, S. Chem. Lett. 1980, 913. See also: ref 7a.
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62. Stille couplings of activated vinyl chlorides are known. See: (a) Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 1607. (b) Liebeskind, L. S.; Yu, M. S.; Yu, R. H.; Wang, J.; Hagen, K. S. J. Am. Chem. Soc. 1993, 115, 9048. (c) May, P. D.; Larsen, S. D. Synlett 1997, 895.
63. Stille couplings of activated vinyl chlorides are known. See: (a) Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 1607. (b) Liebeskind, L. S.; Yu, M. S.; Yu, R. H.; Wang, J.; Hagen, K. S. J. Am. Chem. Soc. 1993, 115, 9048. (c) May, P. D.; Larsen, S. D. Synlett 1997, 895.
64. Stille couplings of activated vinyl chlorides are known. See: (a) Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 1607. (b) Liebeskind, L. S.; Yu, M. S.; Yu, R. H.; Wang, J.; Hagen, K. S. J. Am. Chem. Soc. 1993, 115, 9048. (c) May, P. D.; Larsen, S. D. Synlett 1997, 895.
65. For an excellent review of the mechanisms of the Stille reaction, see: Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
66. Pd-arene interactions in palladium complexes have been proposed to cotribute to their catalytic activity. See (a) Reid, S. M.; Boyle, R. C.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2003, 125, 7856. (b) Catellani, M.; Mealli, C.; Motti, E.; Paoli, P.; Perez-Carreno, E.; Pregosin, P. S. J. Am. Chem. Soc. 2002, 124, 4336. See also: refs 8a, 22c, and 22d.
67. Pd-arene interactions in palladium complexes have been proposed to cotribute to their catalytic activity. See (a) Reid, S. M.; Boyle, R. C.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2003, 125, 7856. (b) Catellani, M.; Mealli, C.; Motti, E.; Paoli, P.; Perez-Carreno, E.; Pregosin, P. S. J. Am. Chem. Soc. 2002, 124, 4336. See also: refs 8a, 22c, and 22d.