Issue 19, 2019
From the journal:

Chemical Science

Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols†

Karsten Donabauer,a   Mitasree Maity, ORCID logo a   Anna Lucia Berger,a   Gregory S. Huff,a   Stefano Crespi ORCID logo a  and  Burkhard König ORCID logo *a  

* Corresponding authors

a Institute of Organic Chemistry, Faculty of Chemistry and Pharmacy, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, Germany
E-mail: burkhard.koenig@ur.de

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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Article information

DOI
https://doi.org/10.1039/C9SC01356C
Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2019,10, 5162-5166

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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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