Radical bicyclization of 1,6-enynes with sulfonyl hydrazides by the use of TBAI/TBHP in the aqueous phase

Fa-Liang Liu; Lan Mei; Ling-Tao Wang; Yu Zhou; Keqi Tang; Ting Li; Rongnan Yi; Wen-Ting Wei

doi:10.1039/d3cc01102j

Radical bicyclization of 1,6-enynes with sulfonyl hydrazides by the use of TBAI/TBHP in the aqueous phase

Chem Commun (Camb). 2023 May 23;59(42):6391-6394. doi: 10.1039/d3cc01102j.

Authors

Fa-Liang Liu¹, Lan Mei¹, Ling-Tao Wang¹, Yu Zhou¹, Keqi Tang¹, Ting Li², Rongnan Yi³, Wen-Ting Wei¹

Affiliations

¹ School of Materials Science and Chemical Engineering, Institute of Mass Spectrometry, Ningbo University, Ningbo, Zhejiang, 315211, China. weiwenting@nbu.edu.cn.
² College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan, 473061, China. chemlt2015@nynu.edu.cn.
³ Criminal Technology Department, Hunan Police Academy, Changsha, Hunan, 410138, China.

PMID: 37157973
DOI: 10.1039/d3cc01102j

Abstract

A novel 5-exo-dig/6-endo-trig bicyclization of 1,6-enynes with sulfonyl hydrazides in the aqueous phase using the cheap and available tetrabutylammonium iodide (TBAI)-tert-butyl hydroperoxide (TBHP) combined system is reported. The resulting reaction of diverse nitrogen- and oxygen-polyheterocycles displays high chemical selectivity, high step-economy, and a moderate substrate scope. Moreover, iodosulfonylation can be realized by modulating the structure of the 1,6-enynes.