Issue 48, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
03 Okt. 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
Creative Commons BY license

Chem. Sci., 2019,10, 10991-10996

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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