Selective α,δ-hydrocarboxylation of conjugated dienes utilizing CO2 and electrosynthesis

To date the majority of diene carboxylation processes afford the α,δ-dicarboxylated product, the selective mono-carboxylation of dienes is a significant challenge and the major product reported under transition metal catalysis arises from carboxylation at the α-carbon. Herein we report a new electro...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-07, Vol.11 (34), p.9109-9114
Main Authors: Sheta, Ahmed M, Mashaly, Mohammad A, Said, Samy B, Elmorsy, Saad S, Malkov, Andrei V, Buckley, Benjamin R
Format: Article
Language:English
Subjects:
Carboxylation
Carboxylic acids
Chemistry
Dicarboxylic acids
Dienes
NMR
Nuclear magnetic resonance
Transition metals
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Summary:To date the majority of diene carboxylation processes afford the α,δ-dicarboxylated product, the selective mono-carboxylation of dienes is a significant challenge and the major product reported under transition metal catalysis arises from carboxylation at the α-carbon. Herein we report a new electrosynthetic approach, that does not rely on a sacrificial electrode, the reported method allows unprecedented direct access to carboxylic acids derived from dienes at the δ-position. In addition, the α,δ-dicarboxylic acid or the α,δ-reduced alkene can be easily accessed by simple modification of the reaction conditions.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc03148h