ja9b03024_si_001.pdf (4.8 MB)
Copper-Catalyzed Trifluoromethylation of Alkyl Bromides
journal contribution
posted on 2019-04-15, 00:00 authored by David
J. P. Kornfilt, David W. C. MacMillanCopper
oxidative addition into organohalides is a challenging two-electron
process. In contrast, formal oxidative addition of copper to Csp2 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 Csp3-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.
History
Usage metrics
Categories
Keywords
Copper-Catalyzed Trifluoromethylationtrifluoromethyl groupstwo-electron processCu-catalyzed cross-couplingnovel paradigmheterobenzyl bromidescopper oxidative additionalkyl bromidesalkyl trifluoromethanessilyl radicalsphotoredox conditionsC sp 3oxidative additionAlkyl Bromides Copper oxidative addition
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC