10.1002/anie.201912450
Angewandte Chemie International Edition
RESEARCH ARTICLE
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spectrum of simple alkene substrates, including styrenes, cyclic
internal alkenes, vinyl ethers, vinyl esters, and unactivated olefins,
to achieve direct acyltrifluoromethylation. Notably, a dearomative
difunctionalization of indoles could be readily achieved in a highly
diastereoselective manner. This protocol was also compatible
with various difluoroalkyl bromides bearing diverse functionalities,
such as sulfonyl, ester, amide, and bromide moieties. Moreover,
perfluoroalkylation could also be realized. With this strategy, over
120 examples of fluoroketones were facilely accessed from
simple feedstock materials. The generality and practicality were
highlighted by the late-stage modification of drug skeletons. In
addition, preliminary results of the catalytic asymmetric version
were achieved, indicating the great potential of NHC catalysis in
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radical-mediated
enantioselective
synthesis.
Further
investigations on the diversity oriented radical transformations
through NHC organocatalysis are currently underway in our
laboratory, and the results will be reported in due cause.
Acknowledgements
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Financial support from NSFC (21871031, 21702021, 81573588
and 81703809), the Science & Technology Department of
Sichuan Province (2017JQ0032), “Thousand Talents Program” of
Sichuan Province, “Chengdu Talents Program” and the start-up
found of Chengdu University is gratefully acknowledged.
Conflict of interest
The authors declare no conflict of interest.
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Keywords: NHC organocatalysis • radical acylfluoroalkylation •
olefin difunctionalization • multicomponent reaction •
fluoroketone
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