CuI-catalyzed regioselective hydrothiolation of alkynes: a thiol-free route to (Z)-β-alkenyl sulfides

Literature Information

Publication Date 2023-12-16
DOI 10.1039/D3OB01230A
Impact Factor 3.876
Authors

Najmeh Nowrouzi, Mohammad Abbasi, Ensieh Safari, Amin Arman


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Abstract

A thiol-free procedure for regioselective preparation of (Z)-β-alkenyl sulfides via a three-component reaction of aryl/alkyl halides, phenylacetylene, and potassium isopropylxanthate in the presence of copper iodide as a catalyst in polyethylene glycol is reported. In this study, a xanthate salt is used as an odorless source of sulfur. The reactions proceed in a one-pot and single-step pathway with the formation of the carbothionate intermediate identified using NMR data as well as exclusively forming the Z isomer.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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