Related Experiment Video
Updated: Jul 15, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
A general and efficient method for the selective synthesis of beta-hydroxy sulfides and beta-hydroxy sulfoxides
Weike Su1, Jiuxi Chen, Huayue Wu
1College of Pharmaceutical Sciences, Zhejiang Key Laboratory of Pharmaceutical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. suweike@zjut.edu.cn
Abstract:
Gallium(III) triflate-catalyzed ring opening of epoxides affords beta-hydroxy sulfides with high regioselectivity and chemoselectivity in high yields (84-97%) under solvent-free conditions. Additionally, a simple, efficient, and environmentally benign one-pot procedure for the synthesis of beta-hydroxy sulfoxides in sole water has been developed for the first time. The process, promoted by a H2O2-Ga(OTf)3 system, affords beta-hydroxy sulfoxides in high yields (81-94%) and high chemoselectivity without any detectable overoxidation to beta-hydroxy sulfones. The catalyst could be recovered easily after the reactions and reused without evident loss of activity.
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Acid Halides to Ketones: Gilman Reagent
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Structure and Nomenclature of Thiols and Sulfides
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
