Synthesis 2017; 49(20): 4698-4702
DOI: 10.1055/s-0036-1588476
paper
© Georg Thieme Verlag Stuttgart · New York

B(C6F5)3-Catalyzed Reduction of Sulfoxides and Sulfones to Sulfides with Hydrosilanes

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany   eMail: martin.oestreich@tu-berlin.de
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Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany   eMail: martin.oestreich@tu-berlin.de
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Publikationsverlauf

Received: 27. Mai 2017

Accepted: 31. Mai 2017

Publikationsdatum:
05. Juli 2017 (eFirst)

Abstract

B(C6F5)3 is shown to catalyze the deoxygenation of sulfoxides and sulfones to the corresponding sulfides with Et3SiH as the stoichiometric hydride source. While the method is limited in terms of functional group tolerance, it is applicable to the reduction of alkyl/aryl-, aryl/aryl-, and alkyl/alkyl-substituted sulfoxides, including the benzyl/benzyl-substituted derivative. The same protocol converts alkyl/aryl- but not aryl/aryl-substituted sulfones into sulfides.

Supporting Information

 
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