Olefination of carbonyls with alkenes enabled by electrophotocatalytic generation of distonic radical cations.

ABSTRACT: The conversion of carbonyls to olefins is a transformation of great importance for complex molecule synthesis. Standard methods use stoichiometric reagents that have poor atom economy and require strongly basic conditions, which limit their functional group compatibility. An ideal solution would be to catalytically olefinate carbonyls under nonbasic conditions using simple and widely available alkenes, yet no such broadly applicable reaction is known. Here, we demonstrate a tandem electrochemical/electrophotocatalytic reaction to olefinate aldehydes and ketones with a broad range of unactivated alkenes. This method involves the oxidation-induced denitrogenation of cyclic diazenes to form 1,3-distonic radical cations that rearrange to yield the olefin products. This olefination reaction is

SUBMITTER: Steiniger KA 

PROVIDER: S-EPMC10104462 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature