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

URN to cite this document:
urn:nbn:de:bvb:355-epub-410212
Berger, Anna Lucia ; Donabauer, Karsten ; König, Burkhard
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Date of publication of this fulltext: 13 Nov 2019 09:11


Abstract

We report a redox‐neutral method for the generation of carbanions from benzylic C–H bonds in a photocatalytic Grignardtype 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.


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