Nickel-catalyzed cross-couplings of organosilicon reagents with unactivated secondary alkyl bromides

Journal of the American Chemical Society

Volumn 126, Issue 25, 2004, Pages 7788-7789

  Powell, David A ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; BROMIDE; FUNCTIONAL GROUP; HALIDE; METAL; NICKEL; ORGANOSILICON DERIVATIVE; REAGENT;

AIR; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CROSS COUPLING REACTION; MOLECULAR STABILITY; STOICHIOMETRY;

CATALYSIS; HYDROCARBONS, BROMINATED; HYDROCARBONS, HALOGENATED; INDICATORS AND REAGENTS; METALS; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; SILICONES;

EID: 3042542346     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047433c     Document Type: Article

References (38)

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18. Couplings with organozirconium compounds: Wiskur, S. L.; Korte, A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 82-83.
19. Sonogashira reactions: Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643. For reactions with alkynyllithiums, see: Yang, L.-M.; Huang, L.-F.; Luh, T.-Y. Org. Lett. 2004, 6, 1461-1463.
20. Sonogashira reactions: Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643. For reactions with alkynyllithiums, see: Yang, L.-M.; Huang, L.-F.; Luh, T.-Y. Org. Lett. 2004, 6, 1461-1463.
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33. 2Me; TBAF; THF, rt)(ref 7) is ineffective (<5% yield).
34. Presumably, the fluoride ion binds to trifluorophenylsilane to generate a hypervalent silicate that efficiently transfers the phenyl group from silicon to nickel. For a discussion, see ref 13.
35. Notes: (a) The stoichiometry of CsF is important: smaller and larger amounts lead to lower yields. (b) Other Lewis bases (e.g., KOSiMe3, NaOH, NaOEt, and KOt-Bu) are ineffective. (c) Addition of 1 equiv of water results in a substantial decrease in yield.
36. Trifluoroarylsilanes are easily prepared from trichloroarylsilanes under a variety of conditions. For example, see: Damrauer, R.; Simon, R. A.; Kanner, B. Organometallics 1988, 7, 1161-1164 and references therein.
37. 2-)Me with Cy-Br). (d) These conditions have not proved to be suitable (<10% yield) for couplings of: primary or secondary alkyl chlorides or tosylates, secondary alkyl halides that bear an electron-withdrawing group in the α or β position, and trifluoroalkenylsilanes.
38. We believe that these reactions proceed via alkyl radicals that combine with nickel to form alkylnickel intermediates. JA047433C