From amides to urea derivatives or carbamates with chemospecific C–C bond cleavage at room temperature?

Organic Chemistry Frontiers Pub Date: 2022-01-21 DOI: 10.1039/D1QO01922H

Abstract

Ureas and carbamates are common motifs in pharmaceuticals, agrochemicals, biologically active compounds and organocatalysis applications. Herein, we report a significant advancement in this area and present a general method for copper-catalyzed chemospecific C–C bond cleavage of amides to synthesize urea derivatives and carbamates at room temperature. A catalytic process via a resonant six-membered N,O-chelated copper cycle and superoxide radical was proposed according to mechanistic and control experiments. The combination of chelation assistance and radical oxygenation strategies opened a door for C–C bond cleavage of common substrates which possess multiple reactive sites and we envision that this broadly applicable method will be of great interest in organic synthesis, the pharmaceutical industry and the agrochemical industry.

Graphical abstract: From amides to urea derivatives or carbamates with chemospecific C–C bond cleavage at room temperature
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