TY - JOUR
T1 - Copper-Catalyzed Trifluoromethylation of Alkyl Bromides
AU - Kornfilt, David J.P.
AU - Macmillan, David W.C.
N1 - Funding Information:
Financial support provided by the NIHGMS (R01 GM093213) and kind gifts from Merck, Janssen, and Pfizer. D. J. P. Kornfilt thanks Mr. Chi Le and Mr. Russell Smith for valuable scientific discussions.
Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/5/1
Y1 - 2019/5/1
N2 - Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to C sp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of C sp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes.
AB - Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to C sp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of C sp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes.
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U2 - 10.1021/jacs.9b03024
DO - 10.1021/jacs.9b03024
M3 - Article
C2 - 30983333
AN - SCOPUS:85065079860
SN - 0002-7863
VL - 141
SP - 6853
EP - 6858
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 17
ER -