Issue 17, 2020

Phenylboronic acid-catalyzed tandem construction of S–S and C–S bonds: a new method for the synthesis of benzyl disulfanylsulfone derivatives from S-benzyl thiosulfonates

Abstract

A unique phenylboronic acid-catalyzed dimerization–sulfonylation of S-benzyl thiosulfonates has been disclosed. A metal-free tandem construction of S–S and C–S bonds is an operationally simple method to access a wide range of benzyl disulfanylsulfone derivatives in high to excellent yields. Moreover, the robustness of this tandem transformation has been demonstrated by gram-scale reactions, and a plausible mechanism is also proposed.

Graphical abstract: Phenylboronic acid-catalyzed tandem construction of S–S and C–S bonds: a new method for the synthesis of benzyl disulfanylsulfone derivatives from S-benzyl thiosulfonates

Supplementary files

Article information

Article type
Communication
Submitted
29 Feb 2020
Accepted
03 Apr 2020
First published
03 Apr 2020

Org. Biomol. Chem., 2020,18, 3243-3248

Phenylboronic acid-catalyzed tandem construction of S–S and C–S bonds: a new method for the synthesis of benzyl disulfanylsulfone derivatives from S-benzyl thiosulfonates

R. Jannapu Reddy, Md. Waheed and G. Rama Krishna, Org. Biomol. Chem., 2020, 18, 3243 DOI: 10.1039/D0OB00442A

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