Paired electrolysis enables decarboxylative coupling of alkenyl acids with diazo compounds?

Organic Chemistry Frontiers Pub Date: 2023-05-17 DOI: 10.1039/D3QO00370A

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
Recommended Literature