Redox-Neutral Decarboxylative Cross-Coupling of Oxamates with Aryl Bromides

ACS Org Inorg Au. 2023 Nov 29;4(2):223-228. doi: 10.1021/acsorginorgau.3c00053. eCollection 2024 Apr 3.

Abstract

Dual nickel-photoredox-enabled direct synthesis of amides through cross-coupling of cesium oxamates with aryl bromides has been developed. This methodology's key advantages are mild reaction conditions, utilizing organic dye as a photocatalyst, employing readily available starting chemicals as coupling partners, and late-stage carbamoylation of pharmaceutically relevant molecules. DFT studies suggested that the nickel catalytic cycle proceeds via a radical addition pathway prior to the oxidative insertion.