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Enantioconvergent Arylation of Racemic Secondary Alcohols to Chiral Tertiary Alcohols Enabled by Nickel/N-Heterocyclic Carbene Catalysis

Yuan Cai and Shi-Liang Shi*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: shiliangshisioc.ac.cn

Y. Cai, S.-L. Shi, J. Am. Chem. Soc., 2021, 143, 11963-11968.

DOI: 10.1021/jacs.1c06614 (free Supporting Information)


Abstract

A chiral N-heterocyclic carbene (NHC)-nickel complex catalyzes an enantioconvergent upgrading reaction of simple racemic secondary alcohols to enantioenriched tertiary alcohols. In this highly efficient formal asymmetric alcohol α-C-H arylation, a dehydrogenation with phenyl triflate as a mild oxidant is followed by asymmetric addition of arylboronic esters to the transient ketones.

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proposed mechanism

(R,R,R,R)-ANIPE



Key Words

arylation


ID: J48-Y2021