Palladium-catalyzed silylation of aryl chlorides with hexamethyldisilane

Organic Letters

Volumn 9, Issue 19, 2007, Pages 3785-3788

  McNeill, Eric ^a   Barder, Timothy E ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHLORIDE; HEXAMETHYLDISILANE; IODINE; LIGAND; PALLADIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON;

BENZENE; CATALYSIS; CHLORIDES; ELECTRONS; IODINE; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; SILANES;

EID: 34848906534     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701518f     Document Type: Article

References (26)

1. (a) Luliñski, S.; Serwatowski, J. J. Org. Chem. 2003, 68, 9384-9388.
2. (b) Manoso, A. S.; Ahn, C.; Soheile, A.; Handy, C. J.; Correia, R.; Seganish, W. M.; DeShong, P. J. Org. Chem. 2004, 69, 8305-8314 and references therein.
3. (a) Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1-C3.
4. (b) Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 409-413.
5. (c) Matsumoto, H.; Shono, K.; Nagai, Y. J. Organomet. Chem. 1981, 208, 145-152.
6. (a) Azarian, D.; Dua, S. S.; Eaborn, C.; Walton, D. R. M. J. Organomet. Chem. 1976, 117, C55-C57.
7. (b) Eaborn, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331-341.
8. (a) Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1987, 28, 4715-4718.
9. (b) Shirakawa, E.; Kurahashi, T.; Yoshida, H.; Hiyama, T. Chem. Commun. 2000, 1895-1896.
10. Babin, P.; Bennetau, B.; Theurig, M.; Dunoguès, J. J. Organomet. Chem. 1993, 446, 135-138.
11. Goossen, L. J.; Ferwanah, A.-R. S. Synlett 2000, 1801-1803.
12. Denmark, S. E.; Kallemeyn, J. M. Org. Lett. 2003, 5, 3483-3486.
13. Yamanoi, Y. J. Org. Chem. 2005, 70, 9607-9609.
14. (a) Rich, J. D. J. Am. Chem. Soc. 1989, 111, 5886-5893.
15. (b) Krafft, T. E.; Rich, J. D.; McDermott, P. J. J. Org. Chem. 1990, 55, 5430-5432.
16. Tobisu, M.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2006, 128, 8152-8153.
17. Hamze, A.; Provot, O.; Alami, M.; Brion, J.-D. Org. Lett. 2006, 8, 931-934.
18. Deffieux, D.; Bordeau, M.; Biran, C.; Dunoguès, J. Organometallics 1994, 13, 2415-2422.
19. Iwasawa, T.; Komano, T.; Tajima, A.; Tokunaga, M.; Obora, Y.; Fujihara, T.; Tsuji, Y. Organometallics 2006, 25, 4665-4669.
20. Recent papers that utilize biaryl phosphines in C-O, C-N, and C-C bond forming processes: (a) Burgos, C. H.; Barder, T. E.; Huang, X.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, A321-A326.
21. (b) Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 6523-6527.
22. (c) Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358-3366.
23. (a) Wilson, S. R.; Jacob, L. A. J. Org. Chem. 1986, 51, 4833-4836.
24. (b) Jacob, L. A.; Chen, B.-L.; Stec, D. Synthesis 1993, 611-614.
25. Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844-14845.
26. For a direct conversion of aryl chlorides to aryl iodides using a solid-supported copper(I) catalyst, see: Clark, J. H.; Jones, C. W. J. Chem. Soc., Chem. Commun. 1987, 1409-1410.