Palladium-Catalyzed Cross-Coupling Reaction of Silicone with Aryl Chlorides

Synlett

Volumn , Issue 12, 2003, Pages 1850-1852

  Koike, Tooru ^a   Mori, Atsunori ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

aq potassium carbonate; Aryl chlorides; Cross coupling; Palladium; Silicone

Indexed keywords

AROMATIC COMPOUND; CHLORIDE; PALLADIUM; POTASSIUM CARBONATE; SILICONE; SILOXANE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ELECTRON TRANSPORT; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVENT EFFECT;

EID: 0142028623     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41413     Document Type: Article

References (26)

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14. Recent palladium-catalyzed cross-coupling reaction of aryl chlorides using organometallic reagents, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (b) Littke, A. F.; Schwarz, L.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (c) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (e) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413. (f) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439. (g) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
15. Recent palladium-catalyzed cross-coupling reaction of aryl chlorides using organometallic reagents, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (b) Littke, A. F.; Schwarz, L.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (c) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (e) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413. (f) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439. (g) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
16. Recent palladium-catalyzed cross-coupling reaction of aryl chlorides using organometallic reagents, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (b) Littke, A. F.; Schwarz, L.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (c) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (e) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413. (f) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439. (g) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
17. Recent palladium-catalyzed cross-coupling reaction of aryl chlorides using organometallic reagents, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (b) Littke, A. F.; Schwarz, L.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (c) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (e) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413. (f) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439. (g) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
18. Recent palladium-catalyzed cross-coupling reaction of aryl chlorides using organometallic reagents, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (b) Littke, A. F.; Schwarz, L.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (c) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (e) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413. (f) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439. (g) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
19. Recent palladium-catalyzed cross-coupling reaction of aryl chlorides using organometallic reagents, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (b) Littke, A. F.; Schwarz, L.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (c) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (e) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413. (f) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439. (g) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
20. Recent palladium-catalyzed cross-coupling reaction of aryl chlorides using organometallic reagents, see: (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (b) Littke, A. F.; Schwarz, L.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387. (c) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411. (e) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413. (f) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439. (g) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
21. 2 was prepared according to the literature procedure, see : Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890.
22. 2O.
23. (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
24. (b) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
25. 2O = 3:1) to yield 52.5 mg of 4-methoxyphenyl (95%).
26. The related mechanism has also been proposed in the Stille coupling reaction of chloroarenes: Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Chem. Commun. 2002, 2608.