Room-temperature Hiyama cross-couplings of arylsilanes with alkyl bromides and iodides

Journal of the American Chemical Society

Volumn 125, Issue 19, 2003, Pages 5616-5617

  Lee, Jae Young ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; BROMIDE; IODIDE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; ROOM TEMPERATURE;

CATALYSIS; HYDROCARBONS; HYDROCARBONS, BROMINATED; HYDROCARBONS, IODINATED; PALLADIUM; SILANES; TEMPERATURE;

EID: 0037620677     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0349352     Document Type: Article

References (16)

1. For a review of the Hiyama reaction, see: Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 10. See also: Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61.
2. For a review of the Hiyama reaction, see: Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 10. See also: Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61.
3. For some recent developments in Hiyama cross-coupling chemistry, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846. (b) Itami, K.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2001, 123, 5600-5601 and references therein.
4. For some recent developments in Hiyama cross-coupling chemistry, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846. (b) Itami, K.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2001, 123, 5600-5601 and references therein.
5. 3-X electrophiles, see: Cardenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387. See also: Luh, T.-Y.; Leung, M.-k.; Wong, K.-T. Chem. Rev. 2000, 100, 3187-3204.
6. 3-X electrophiles, see: Cardenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387. See also: Luh, T.-Y.; Leung, M.-k.; Wong, K.-T. Chem. Rev. 2000, 100, 3187-3204.
7. (a) Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099-10100.
8. (b) Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.
9. (c) Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910-3912.
10. (d) Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662-13663.
11. Frisch, A. C.; Shaikh, N.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 4056-4059.
12. Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718-3719.
13. 2Cl) do not cross-couple with n-dodecyl bromide (<2% yield).
14. For examples in which phosphines and their corresponding phosphonium salts can be used interchangeably in palladium-catalyzed coupling processes, see: (a) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298. (b) References 4d and 6.
15. For examples in which phosphines and their corresponding phosphonium salts can be used interchangeably in palladium-catalyzed coupling processes, see: (a) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298. (b) References 4d and 6.
16. 4 (#15-1023).