Issue 12, 2023

Paired electrolysis enables decarboxylative coupling of alkenyl acids with diazo compounds

Abstract

Herein, we have reported an efficient and green paired electrolysis strategy for decarboxylative coupling of alkenyl acids with diazo compounds, providing a broad range of β,γ-alkenyl esters and amides. The method features high stereoselectivity and no involvement of transition metals and chemical redox regents. Moreover, the protocol also provides a facile access to the corresponding dideuterated products with a high level of deuterium incorporation (93–99% D-inc.) by directly using D2O, thus unveiling the method as being highly valuable. Mechanistic studies reveal that diazo compounds are converted into carbon radicals using H2O as a promoter at the cathode through a proton-coupled electron transfer (PCET) process.

Graphical abstract: Paired electrolysis enables decarboxylative coupling of alkenyl acids with diazo compounds

Supplementary files

Article information

Article type
Research Article
Submitted
10 Mar 2023
Accepted
15 Apr 2023
First published
17 May 2023

Org. Chem. Front., 2023,10, 2968-2975

Paired electrolysis enables decarboxylative coupling of alkenyl acids with diazo compounds

J. Jiao, Y. Yan, Q. Ke, Y. Zhang, H. Huang, Q. Gao, J. Liu and X. Wang, Org. Chem. Front., 2023, 10, 2968 DOI: 10.1039/D3QO00370A

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