Jump to main content
Jump to site search


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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 03 Oct 2019, accepted on 11 Nov 2019 and first published on 12 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC04987H
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

  •   Request permissions

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

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

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements