Practical synthesis of unsymmetrical disulfides promoted by bromodimethylsulfonium bromide. Issue 5 (10th January 2023)

• Record Type: Journal Article
• Authors: Dong, Bo; Chen, Yifeng; Xie, Shubing; Zhang, Jieying; Shen, Jian; Xie, Lan-Gui
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 5(2023)
• Page Start: 930
• Page End: 934
• Publication Date: 2023-01-10
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob02124b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We present the synthesis of unsymmetrical disulfides where the homo-coupling of the thiols is inhibited by adding the thiols sequentially via rapid oxidation using bromodimethylsulfonium bromide. Abstract : Oxidative cross-coupling of two thiols is the most direct tool for the synthesis of unsymmetrical disulfides and highly desirable across academia and industry. However, the inevitable formation of significant amounts of the corresponding symmetrical by-products is a major issue. We herein present a method toward the synthesis of unsymmetrical disulfides in which the homo-coupling of the thiols is effectively inhibited by adding the two thiols sequentially, taking advantage of rapid oxidation of the thiol by bromodimethylsulfonium bromide.