Issue 20, 2021

Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o-nitroaryl ureas

Abstract

A simple and facile strategy to construct o-nitroaryl urea employing carbodiimides and ceric ammonium nitrate (CAN) has been developed. This protocol achieves the installation of two functional groups in one step with high functional group compatibility. Control experiments show that the reaction mechanism involves an intriguingly concerted nitration/ureation process enabled by CAN, and is distinctive from conventional electrophilic nitrification. The oxygen atom of urea probably originates from the nitrate ions provided by CAN. The late-stage derivatization and gram-scale synthesis reveal the promising utility of this methodology.

Graphical abstract: Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o-nitroaryl ureas

Supplementary files

Article information

Article type
Research Article
Submitted
24 Jun 2021
Accepted
10 Aug 2021
First published
11 Aug 2021

Org. Chem. Front., 2021,8, 5771-5776

Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o-nitroaryl ureas

S. Wang, X. Xie, X. Zhao, J. Liu, Z. Zhao, J. Chen, J. Li, K. Sun and Z. Zhang, Org. Chem. Front., 2021, 8, 5771 DOI: 10.1039/D1QO00943E

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