I2/TBPB mediated oxidative reaction of N-tosylhydrazones with anilines: practical construction of 1,4-disubstituted 1,2,3-triazoles under metal-free and azide-free conditions

Zhong-Jian Cai; Xin-Mou Lu; You Zi; Chao Yang; Ling-Jie Shen; Jian Li; Shun-Yi Wang; Shun-Jun Ji

doi:10.1021/ol502431b

I2/TBPB mediated oxidative reaction of N-tosylhydrazones with anilines: practical construction of 1,4-disubstituted 1,2,3-triazoles under metal-free and azide-free conditions

Org Lett. 2014 Oct 3;16(19):5108-11. doi: 10.1021/ol502431b. Epub 2014 Sep 24.

Authors

Zhong-Jian Cai¹, Xin-Mou Lu, You Zi, Chao Yang, Ling-Jie Shen, Jian Li, Shun-Yi Wang, Shun-Jun Ji

Affiliation

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University , Suzhou 215123, China.

PMID: 25250817
DOI: 10.1021/ol502431b

Abstract

An efficient I2 (20 mol %)/TBPB mediated oxidative formal [4 + 1] cycloaddition of N-tosylhydrazones with anilines via C-N/N-N bond formation and S-N cleavage has been developed. This protocol represents a simple, general, and efficient approach for the construction of 1,2,3-triazoles under metal-free and azide-free conditions by utilizing a catalytic amount of I2.