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Issue 9, 2020
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Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters

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Abstract

A cross-dehydrogenative coupling strategy for enantioselective access to acyclic CF3-substituted all-carbon quaternary stereocenters has been established. By using catalytic DDQ with MnO2 as an inexpensive terminal oxidant, asymmetric cross coupling of racemic δ-CF3-substituted phenols with indoles proceeded smoothly, providing CF3-bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivities. The generality of the strategy is further demonstrated by efficient construction of all-carbon quaternary stereocenters bearing other polyfluoroalkyl and perfluoroalkyl groups such as CF2Cl, C2F5, and C3F7.

Graphical abstract: Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters

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Supplementary files

Article information


Submitted
20 Nov 2019
Accepted
09 Jan 2020
First published
29 Jan 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 2414-2419
Article type
Edge Article

Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters

X. Pan, Z. Wang, L. Kan, Y. Mao, Y. Zhu and L. Liu, Chem. Sci., 2020, 11, 2414
DOI: 10.1039/C9SC05894J

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