4.8 Article

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

Journal

GREEN CHEMISTRY
Volume 24, Issue 16, Pages -

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc01256a

Keywords

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Funding

  1. NSFC [21871257, 22022111, 22001250]
  2. Natural Science Foundation of Fujian Province [2020J02008]
  3. scientific research innovation program Xiyuanjiang River Scholarship of College of Life Sciences, Fujian Normal University [22FSSK006]

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This study reports a method of using light to drive a regioselective carbocarboxylation reaction between CO2 and aryl and alkyl halides. This method allows for the rapid and highly regioselective synthesis of complex β,γ-unsaturated carboxylic acids.
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 beta,gamma-unsaturated carboxylic acids from easily available 1,3-dienes and organic halides with CO2.

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