Selective ruthenium-catalyzed hydrochlorination of alkynes: one-step synthesis of vinylchlorides

Angewandte Chemie
Sylvie DérienChristian Bruneau

Abstract

An unprecedented ruthenium-catalyzed direct and selective alkyne hydrochlorination is reported and leads to vinylchlorides in excellent yields with atom economy. The reaction proceeds at room temperature from terminal alkynes and provides a variety of chloroalkenes. Only the regioisomer resulting from the formal Markovnikov addition is selectively formed. Mechanistic studies show the stereoselective syn addition of HCl to alkynes at room temperature and suggest a chloro hydrido Ru(IV) species as a key intermediate of the reaction.

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Citations

Jun 25, 2016·Chemical Reviews·David A PetroneMark Lautens
Feb 15, 2017·Journal of the American Chemical Society·David A PetroneMark Lautens
Mar 8, 2017·Journal of the American Chemical Society·Joseph DerosaKeary M Engle
Feb 28, 2019·Angewandte Chemie·Yong Ho Lee, Bill Morandi
Jun 6, 2019·Organic & Biomolecular Chemistry·Ritush Kumar, Radhey M Singh
Aug 2, 2017·Chemistry : a European Journal·Zhou LiBo Xu
Apr 30, 2017·Angewandte Chemie·Judit Oliver-MeseguerAvelino Corma
Apr 4, 2017·ACS Omega·Kengo MuragishiNagatoshi Nishiwaki
Dec 15, 2018·Journal of the American Chemical Society·Weiqiang ChenMartin Oestreich
Oct 24, 2020·Journal of the American Chemical Society·Nagaraju BarsuAlois Fürstner

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