Issue 24, 2022

Widely applicable (radio)dihalogenation of alkynes and alkenes using two different nucleophilic alkali metal halides

Abstract

We have developed a hydrogen bond network-assisted highly regio- and stereoselective (radio)dihalogenation of alkynes and alkenes using two nucleophilic alkali metal salts (MX1/MX2, X1, X2 = Cl, Br, I, SCN, 125I). This protocol is general and works for diverse halogen combinations. This transition metal-free system produces good chemical yields and excellent regio- and stereo-selectivity for a wide range of alkynes and alkenes with good functional group tolerance. In addition, the conditions are mild and hazardous reagents are not required.

Graphical abstract: Widely applicable (radio)dihalogenation of alkynes and alkenes using two different nucleophilic alkali metal halides

Supplementary files

Article information

Article type
Research Article
Submitted
08 Aug 2022
Accepted
15 Oct 2022
First published
21 Oct 2022

Org. Chem. Front., 2022,9, 6826-6832

Widely applicable (radio)dihalogenation of alkynes and alkenes using two different nucleophilic alkali metal halides

S. Liu, Y. Zhang, K. Gong, X. Zeng, F. Xie, B. Xu and J. Han, Org. Chem. Front., 2022, 9, 6826 DOI: 10.1039/D2QO01276F

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