Pd2(dba)3/P(i-BuNCH2CH2) 3N-catalyzed Stille cross-coupling of aryl chlorides

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1421-1424

  Su, Weiping ^a   Urgaonkar, Sameer ^a   Verkade, John G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; CHLORINE DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND; ORGANOTIN COMPOUND; PALLADIUM COMPLEX; PHOSPHORUS DERIVATIVE; PROAZAPHOSPHATRANE DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; STILLE REACTION;

EID: 2442598164     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0495927     Document Type: Article

References (42)

1. For reviews on Stille cross-coupling reaction, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (c) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. 2002, 41, 4176.
2. For reviews on Stille cross-coupling reaction, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (c) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. 2002, 41, 4176.
3. For reviews on Stille cross-coupling reaction, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1. (c) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. 2002, 41, 4176.
4. For applications of the Stille reaction in natural product synthesis, see: (a) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupalli, 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) Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122, 12169.
5. For applications of the Stille reaction in natural product synthesis, see: (a) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupalli, 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) Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122, 12169.
6. For applications of the Stille reaction in natural product synthesis, see: (a) Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupalli, 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) Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122, 12169.
7. 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. 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.
8. 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. 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.
9. 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. 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.
10. 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. 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.
11. 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. 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.
12. 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. 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.
13. 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. 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.
14. 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. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. For Pd-catalyzed Stille reactions of activated aryl chlorides, see: Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301. See also refs 1b and 1c.
24. (a) Littke, A. F.; Fu, G. C. Angew Chem., Int. Ed. 1999, 38, 2411.
25. (b) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
26. Available from Strem Chemicals.
27. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
28. Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119.
29. Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2003, 124, 14127.
30. Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551.
31. For recent reviews, see: (a) Verkade, J. G. Top. Curr. Chem. 2002, 233, 1. (b) Kisanga, P. B.; Verkade, J. G. Tetrahedron 2003, 59, 7819. (c) Verkade, J. G.; Kisanga, P. B. Aldrichimica Acta, in press.
32. For recent reviews, see: (a) Verkade, J. G. Top. Curr. Chem. 2002, 233, 1. (b) Kisanga, P. B.; Verkade, J. G. Tetrahedron 2003, 59, 7819. (c) Verkade, J. G.; Kisanga, P. B. Aldrichimica Acta, in press.
33. For recent reviews, see: (a) Verkade, J. G. Top. Curr. Chem. 2002, 233, 1. (b) Kisanga, P. B.; Verkade, J. G. Tetrahedron 2003, 59, 7819. (c) Verkade, J. G.; Kisanga, P. B. Aldrichimica Acta, in press.
34. (a) Urgaonkar, S. Nagarajan, M.; Verkade, J. G. J. Org. Chem. 2003, 68, 452.
35. (b) You, J.; Verkade, J. G. Angew. Chem., Int. Ed. 2003, 42, 5051.
36. (c) You, J.; Verkade, J. G. J. Org. Chem. 2003, 68, 8003. Also see refs 3h and 4h.
37. For Pd-arene interactions in palladium complexes, see: (a) Reid, S. M.; Boyle, R. C.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2003, 125, 7816. (b) Catellani, M.; Mealli, C.; Motti, E.; Paoli, P.; Perez-Carreno, E.; Pregosin, P. S. J. Am. Chem. Soc. 2002, 124, 4336. (c) Yin, J.; Rainka, M. P.; Zhang, X.; Buchwald. S. L. J. Am. Chem. Soc. 2002, 124, 1162.
38. For Pd-arene interactions in palladium complexes, see: (a) Reid, S. M.; Boyle, R. C.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2003, 125, 7816. (b) Catellani, M.; Mealli, C.; Motti, E.; Paoli, P.; Perez-Carreno, E.; Pregosin, P. S. J. Am. Chem. Soc. 2002, 124, 4336. (c) Yin, J.; Rainka, M. P.; Zhang, X.; Buchwald. S. L. J. Am. Chem. Soc. 2002, 124, 1162.
39. For Pd-arene interactions in palladium complexes, see: (a) Reid, S. M.; Boyle, R. C.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2003, 125, 7816. (b) Catellani, M.; Mealli, C.; Motti, E.; Paoli, P.; Perez-Carreno, E.; Pregosin, P. S. J. Am. Chem. Soc. 2002, 124, 4336. (c) Yin, J.; Rainka, M. P.; Zhang, X.; Buchwald. S. L. J. Am. Chem. Soc. 2002, 124, 1162.
40. Ligand 1d is commercially available from Aldrich and Strem Chemicals.
41. 4NF (2.2 mmol) inside a glovebox. If the aryl chloride (1.0 mmol) was a solid, it was also added at this time. The flask was capped with a rubber septum and removed from the glovebox. Ligand 1 (6.0 mol %) was then added via syringe from a stock solution (2 mM in dioxane). Aryl chloride (if a liquid, 1.0 mmol), tin reagent (1.1 mmol), and dioxane (2 mL) were then successively added via syringe. Under a positive pressure of argon, the flask was sealed with a Teflon screw-cap, and then the reaction mixture was heated at the temperature indicated (see Tables 1-3) until the starting material had been completely consumed as judged by TLC. The mixture was then cooled to room temperature, diluted with ether or acetone, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel.
42. Further studies on the Stille reaction of aryl chlorides with various substituted aryl tin reagents are ongoing and will be reported in due course.