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

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. Moreove...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-05, Vol.18 (17), p.3243-3248
Main Authors: Jannapu Reddy, Raju, Waheed, Md, Rama Krishna, Gamidi
Format: Article
Language:English
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Summary: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. A novel and unique phenylboronic acid-catalyzed tandem construction of S-S and C-S bonds via dimerization-sulfonylation has been disclosed for the synthesis of benzyl disulfanylsulfone derivatives.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00442a