Enantioselective Silylation of Aliphatic C−H Bonds for the Synthesis of Silicon‐Stereogenic Dihydrobenzosiloles. (28th September 2020)

• Record Type: Journal Article
• Authors: Yang, Bo; Yang, Wu; Guo, Yonghong; You, Lijun; He, Chuan
• Is Part Of: Angewandte Chemie. Volume 132:Number 49(2020)
• Page Start: 22401
• Page End: 22406
• Publication Date: 2020-09-28
• Subjects: asymmetric catalysis -- C(sp3)−H silylation -- dihydrobenzosiloles -- hydrosilylation -- silanes; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202009912
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A rhodium(I)‐catalyzed enantioselective silylation of aliphatic C−H bonds for the synthesis of silicon‐stereogenic dihydrobenzosiloles is demonstrated. This reaction involves a highly enantioselective intramolecular C(sp 3 )−H silylation of dihydrosilanes, followed by a stereospecific intermolecular alkene hydrosilylation leading to the asymmetrically tetrasubstituted silanes. A wide range of dihydrosilanes and alkenes displaying various functional groups are compatible with this process, giving access to a variety of highly functionalized silicon‐stereogenic dihydrobenzosiloles in good to excellent yields and enantioselectivities. Abstract : A rhodium(I)‐catalyzed enantioselective silylation of aliphatic C−H bonds for the synthesis of silicon‐stereogenic dihydrobenzosiloles is demonstrated. It involves a highly enantioselective C−H silylation of dihydrosilanes, followed by a stereospecific alkene hydrosilylation. A wide range of dihydrosilanes and alkenes with various functional groups are compatible, giving access to a variety of functionalized silicon‐stereogenic dihydrobenzosiloles.