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

Author:

Sun ZhankuiORCID,Zhang Xue,Liang Nuoyu,Li Ruining

Abstract

AbstractCarbon–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.

Funder

Shanghai Jiao Tong University

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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