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Org Lett. 2019 Apr 19;21(8):2565-2568. doi: 10.1021/acs.orglett.9b00502. Epub 2019 Apr 08.

Rhodium-Catalyzed Reaction of Azobenzenes and Nitrosoarenes toward Phenazines.

Organic letters

Yan Xiao, Xiaopeng Wu, Hepan Wang, Song Sun, Jin-Tao Yu, Jiang Cheng

Affiliations

  1. School of Petrochemical Engineering, and Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology , Changzhou University , Changzhou 213164 , P.R. China.

PMID: 30958684 DOI: 10.1021/acs.orglett.9b00502

Abstract

A rhodium-catalyzed annulative reaction between azobenzenes and nitrosoarenes has been developed, leading to a series of phenazines in moderate to good yields. This procedure proceeds with sequential chelation-assisted addition of aryl C-H to nitrosoarenes and ring closure by electrophilic attack of azo group to aryl. During this transformation, the azo group served as not only a traceless directing group but also a building block in the final products.

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