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Catalyst-free hydrothiolation of alkynes with dithiocarbamic acids

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Abstract

A highly regio- and stereocontrolled procedure for the synthesis of vinyl dithiocarbamates via catalyst-free hydrothiolation of unactivated alkynes with in situ prepared dithiocarbamic acids with total atom economy is reported. While unactivated terminal alkynes afforded the Markovnikov adducts with excellent regioselectivity, ethynyltrimethylsilane furnished the E-selective anti-Markovnikov adducts with excellent regio- and stereoselectivity. In addition, the obtained vinyl dithiocarbamates were applied as efficient precursors for the synthesis of secondary thiols and α-hydroxythioamides.

Graphical abstract: Catalyst-free hydrothiolation of alkynes with dithiocarbamic acids

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Publication details

The article was received on 07 Dec 2018, accepted on 02 Jan 2019 and first published on 02 Jan 2019


Article type: Communication
DOI: 10.1039/C8CC09726G
Citation: Chem. Commun., 2019, Advance Article
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    Catalyst-free hydrothiolation of alkynes with dithiocarbamic acids

    A. Ziyaei Halimehjani and B. Breit, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09726G

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