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Issue 19, 2019
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Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols

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Abstract

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

Graphical abstract: Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols

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Supplementary files

Article information


Submitted
19 Mar 2019
Accepted
15 Apr 2019
First published
16 Apr 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, 5162-5166
Article type
Edge Article

Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols

K. Donabauer, M. Maity, A. L. Berger, G. S. Huff, S. Crespi and B. König, Chem. Sci., 2019, 10, 5162
DOI: 10.1039/C9SC01356C

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