Issue 26, 2022
From the journal:

RSC Advances

Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide†

Xiaohong Wang,‡a   Fengzhi You,‡a   Baojian Xiong,a   Lei Chen,a   Xuemei Zhang*a  and  Zhong Lian ORCID logo *a  

* Corresponding authors

a Department of Dermatology, State Key Laboratory of Biotherapy and Cancer Center, National Clinical Research Center for Geriatrics, West China Hospital, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
E-mail: xuemeizhang@scu.edu.cn, lianzhong@scu.edu.cn

Abstract

A metal- and base-free 5-endo-trig sulfonylative cyclization between 1,5-dienes, aryldiazonium salts and SO2 (from SOgen) is presented. This method could successfully produce sulfonylated pyrrolin-2-ones in one pot with excellent regioselectivity and good-to-excellent yields. This strategy features mild reaction conditions and broad substrate scope. Moreover, a scale-up reaction and three synthetic applications demonstrate the practicality of this method. Lastly, control experiments indicate that the 5-endo-trig sulfonylative cyclization may proceed in a radical pathway.

Graphical abstract: Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide

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Article information

DOI
https://doi.org/10.1039/D2RA03034A
Article type
Paper
Submitted
13 May 2022
Accepted
31 May 2022
First published
06 Jun 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 16745-16750

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Metal- and base-free tandem sulfonylation/cyclization of 1,5-dienes with aryldiazonium salts via the insertion of sulfur dioxide

X. Wang, F. You, B. Xiong, L. Chen, X. Zhang and Z. Lian, RSC Adv., 2022, 12, 16745 DOI: 10.1039/D2RA03034A

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