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Issue 48, 2019
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Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions

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Abstract

We report a redox-neutral method for the generation of carbanions from benzylic C–H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced in situ by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcohols.

Graphical abstract: Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions

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Supplementary files

Article information


Submitted
03 Oct 2019
Accepted
11 Nov 2019
First published
12 Nov 2019

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

Chem. Sci., 2019,10, 10991-10996
Article type
Edge Article

Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions

A. L. Berger, K. Donabauer and B. König, Chem. Sci., 2019, 10, 10991
DOI: 10.1039/C9SC04987H

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