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Molecules 2015, 20(9), 16709-16722; doi:10.3390/molecules200916709

pH-Dependence of the Aqueous Phase Room Temperature Brønsted Acid-Catalyzed Chemoselective Oxidation of Sulfides with H2O2

1
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
2
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 13 July 2015 / Revised: 1 September 2015 / Accepted: 2 September 2015 / Published: 14 September 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [771 KB, uploaded 14 September 2015]   |  

Abstract

A pH-dependence of the Brønsted acid-catalyzed oxidation of sulfides to the corresponding sulfoxides with H2O2 is reported for the first time based on our systematic investigation of the catalytic performance of a series of Brønsted acids. For all of the Brønsted acids investigated, the catalytic performances do not depend on the catalyst loading (mol ratio of Brønsted acid to substrate), but rather depend on the pH value of the aqueous reaction solution. All of them can give more than 98% conversion and selectivity in their aqueous solution at pH 1.30, no matter how much the catalyst loading is and what the Brønsted acid is. This pH-dependence principle is a very novel perspective to understand the Brønsted-acid catalysis system compared with our common understanding of the subject. View Full-Text
Keywords: sulfide; oxidation; sulfoxide; pH-dependence; Brønsted acid sulfide; oxidation; sulfoxide; pH-dependence; Brønsted acid
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Shen, H.-M.; Zhou, W.-J.; Ma, X.; Wu, H.-K.; Yu, W.-B.; Ai, N.; Ji, H.-B.; Shi, H.-X.; She, Y.-B. pH-Dependence of the Aqueous Phase Room Temperature Brønsted Acid-Catalyzed Chemoselective Oxidation of Sulfides with H2O2. Molecules 2015, 20, 16709-16722.

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