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Application of Halogen-Bonding Catalysis for Markovnikov-Type Hydrothiolation of Alkenes

Synlett, ISSN: 1437-2096, Vol: 34, Issue: 4, Page: 379-387
2023
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Carbon-sulfur bond-formation reactions are applied widely in organic synthesis and chemical biology. Hydrothiolation of alkenes provides a direct way to build carbon-sulfur bonds. Most known methods proceed via radical processes and result in anti-Markovnikov-type products. Herein, we demonstrate that I2 catalyzes the hydrothiolation of alkenes and provides Markovnikov-type products in good to excellent yields. Titration studies revealed that thiol was activated by I2 through halogen bonding. This metal-free reaction has advantages such as green and mild conditions, high functionality tolerance, broad substrate scope, and atom economy. Its application was further demonstrated in peptide syntheses.

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