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

Berger, Anna Lucia, Donabauer, Karsten and König, Burkhard (2019) Photocatalytic carbanion generation from C–H bonds – Reductant free Barbier/Grignard-type reactions. Chemical Science.

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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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Item type:Article
Date:2019
Institutions:Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Projects:DFG KO 1537/18-1, European Union´s Horizon 2020 No. 741623
Identification Number:
ValueType
10.1039/C9SC04987HDOI
Keywords:Photocatalysis; Carbanions; HAT catalysis; Grignard reaction; Barbier reaction
Dewey Decimal Classification:500 Science > 540 Chemistry & allied sciences
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Yes
Item ID:41021
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