Issue 20, 2024

Lewis acid catalyzed Markovnikov hydrobromination and hydrochlorination of alkynes using TMSX (X = Br, Cl)

Abstract

Markovnikov hydrobromination and hydrochlorination of alkynes were achieved using TMSX (X = Br, Cl) instead of corrosive HX (X = Br, Cl) as the bromination and chlorination reagents. Mn(OAc)2·4H2O was used as the hydrobromination catalyst for electron-neutral/rich alkynes. For the hydrobromination of electron-deficient alkynes and hydrochlorination of alkynes, Zn(OAc)2·2H2O was employed as the catalyst. Mechanistic studies suggested that the in situ formed TMS-substituted alkyne might be a reactive intermediate and the proton of the terminal alkyne should be a hydrogen source for the hydrohalogenation reaction.

Graphical abstract: Lewis acid catalyzed Markovnikov hydrobromination and hydrochlorination of alkynes using TMSX (X = Br, Cl)

Supplementary files

Article information

Article type
Communication
Submitted
13 Apr 2024
Accepted
30 Apr 2024
First published
01 May 2024

Org. Biomol. Chem., 2024,22, 4062-4066

Lewis acid catalyzed Markovnikov hydrobromination and hydrochlorination of alkynes using TMSX (X = Br, Cl)

D. Shen, D. Cao, R. Zhang, P. Bai and Z. Liu, Org. Biomol. Chem., 2024, 22, 4062 DOI: 10.1039/D4OB00608A

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