Rhodium(III)-Catalyzed Directed C-H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles

Yanyu Chen; Rong Zhang; Qiujun Peng; Lanting Xu; XianHua Pan

doi:10.1002/asia.201701287

Rhodium(III)-Catalyzed Directed C-H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles

Chem Asian J. 2017 Nov 2;12(21):2804-2808. doi: 10.1002/asia.201701287. Epub 2017 Oct 12.

Authors

Yanyu Chen¹, Rong Zhang¹, Qiujun Peng¹, Lanting Xu², XianHua Pan²

Affiliations

¹ School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, P.R. China.
² Shanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Road, Shanghai, 200232, P.R. China.

PMID: 29024502
DOI: 10.1002/asia.201701287

Abstract

An efficient rhodium-catalyzed direct C-H amidation of N-nitrosoanilines with 1,4,2-dioxazol-5-ones as amidating agents has been developed. This method featured mild reaction conditions, a wide substrate scope and satisfactory yields. Besides, the amidated products could be readily converted to pharmaceutically valuable 1,2-disubstituted benzimidazoles via an HCl-mediated deprotection/cyclization process in one pot.

Keywords: C−H activation; N-nitrosoanilines; benzimidazoles; domino reactions; rhodium.