Remote radical alkynylation of unactivated C(sp3)–H bonds of ethynesulfonamides

Pan Zhou; Mengru Guo; Jiawei Li; Xu Li; Danyang Xie; Bo Qin; Yong Xia

doi:10.1039/D5CC01215E

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Remote radical alkynylation of unactivated C(sp³)–H bonds of ethynesulfonamides†

Pan Zhou,‡^a Mengru Guo,‡^a Jiawei Li,^a Xu Li,^a Danyang Xie,*^b Bo Qin

*^a and Yong Xia

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China
E-mail: qinbo@cqu.edu.cn, xiayong@cqu.edu.cn

^b School of Smart Health, Chongqing College of Electronic Engineering, Chongqing 401331, China
E-mail: xiedanyang@cqcet.edu.cn

Abstract

We report an efficient protocol for the construction of δ-alkynyl amides via 1,5-hydrogen atom transfer and alkynyl group transfer of ethynesulfonamides. The readily installed ethynesulfonamides serve as both an amidyl radical precursor and an alkyne source. This reaction features excellent site selectivity for tertiary, secondary, primary, and benzylic C(sp³)–H bonds.

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Article information

DOI: https://doi.org/10.1039/D5CC01215E
Article type: Communication
Submitted: 05 Mar 2025
Accepted: 10 Apr 2025
First published: 10 Apr 2025

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Chem. Commun., 2025,61, 7109-7112

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Remote radical alkynylation of unactivated C(sp³)–H bonds of ethynesulfonamides

P. Zhou, M. Guo, J. Li, X. Li, D. Xie, B. Qin and Y. Xia, Chem. Commun., 2025, 61, 7109 DOI: 10.1039/D5CC01215E

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Chemical Communications