Issue 5, 2022

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
26 Dec 2021
Accepted
18 Jan 2022
First published
21 Jan 2022

Org. Chem. Front., 2022,9, 1354-1363

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

C. Lv, D. Liu, T. Muschin, C. Bai, A. Bao and Y. Bao, Org. Chem. Front., 2022, 9, 1354 DOI: 10.1039/D1QO01922H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements