Organic letters

Fluorous dimethyl sulfide: A convenient, odorless, recyclable borane carrier

D Crich, S Neelamkavil

Index: Crich, David; Neelamkavil, Santhosh Organic Letters, 2002 , vol. 4, # 23 p. 4175 - 4177

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Citation Number: 35

Abstract

Borane gas and 2-(perfluorooctyl) ethyl methyl sulfide form a solid comprised of an approximately 1: 1 mixture (fluorous BMS) of sulfide and the corresponding sulfide-borane. Fluorous BMS permits hydroboration of alkenes in a dichloromethane/perfluorinated hydrocarbon mixture with subsequent recycling of the fluorous sulfide by fluorous extraction. The use of fluorous BMS in the asymmetric reduction of ketones catalyzed by a chiral ...