Issue 16, 2022

Visible-light-driven regioselective carbocarboxylation of 1,3-dienes with organic halides and CO2

Abstract

Harnessing light to convert carbon dioxide (CO2) into value-added fine chemicals is an attractive synthesis strategy. Herein, we report an unprecedented visible-light-driven regioselective carbocarboxylation of 1,3-dienes with CO2 using aryl and alkyl halides under mild conditions with low-cost potassium formate (HCOOK) to produce carbon dioxide radical anions as the potent reducing agent for the challenging organic halide reduction. Highly 3,4-regioselective carbocarboxylation was achieved with 1,1-diaryl-substituted 1,3-dienes, while major 1,4-carbocarboxylation products were obtained with less hindered mono-aryl substituted 1,3-dienes. This protocol renders a rapid method for producing complex β,γ-unsaturated carboxylic acids from easily available 1,3-dienes and organic halides with CO2.

Graphical abstract: Visible-light-driven regioselective carbocarboxylation of 1,3-dienes with organic halides and CO2

Supplementary files

Article information

Article type
Communication
Submitted
01 Eph 2022
Accepted
19 Mey 2022
First published
23 Mey 2022

Green Chem., 2022,24, 6100-6107

Visible-light-driven regioselective carbocarboxylation of 1,3-dienes with organic halides and CO2

C. Zhou, X. Wang, L. Yang, L. Fu and G. Li, Green Chem., 2022, 24, 6100 DOI: 10.1039/D2GC01256A

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