Issue 42, 2023
From the journal:

Chemical Communications

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

Fa-Liang Liu,a   Lan Mei,a   Ling-Tao Wang,a   Yu Zhou,a   Keqi Tang, ORCID logo *a   Ting Li, ORCID logo *b   Rongnan Yic  and  Wen-Ting Wei ORCID logo *a  

* Corresponding authors

a School of Materials Science and Chemical Engineering, Institute of Mass Spectrometry, Ningbo University, Ningbo, Zhejiang, China
E-mail: weiwenting@nbu.edu.cn, tangkeqi@nbu.edu.cn

b College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan, China
E-mail: chemlt2015@nynu.edu.cn

c Criminal Technology Department, Hunan Police Academy, Changsha, Hunan, China

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.

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

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Article information

DOI
https://doi.org/10.1039/D3CC01102J
Article type
Communication
Submitted
06 Mar 2023
Accepted
28 Apr 2023
First published
28 Apr 2023

Chem. Commun., 2023,59, 6391-6394

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

F. Liu, L. Mei, L. Wang, Y. Zhou, K. Tang, T. Li, R. Yi and W. Wei, Chem. Commun., 2023, 59, 6391 DOI: 10.1039/D3CC01102J

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