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Enantioselective Intermolecular C−H Silylation of Heteroarenes for the Synthesis of Acyclic Si‐Stereogenic Silanes

Shuyou Chen, Jiefeng Zhu, Jie Ke, Yingzi Li, Chuan He

2022Angewandte Chemie15 citationsDOI

Abstract

Abstract Intermolecular C−H silylation for the synthesis of acyclic silanes bearing a silicon‐stereogenic center in one enantiomeric form remains unknown to date. Herein, we report the first enantioselective intermolecular C−H silylation of heteroarenes for the synthesis of acyclic silicon‐stereogenic heteroarylsilanes. This process undergoes a rhodium‐catalyzed direct intermolecular dehydrogenative Si−H/C−H cross‐coupling, giving access to a variety of acyclic heteroarylated silicon‐stereogenic monohydrosilanes, including bis‐Si‐stereogenic silanes, in decent yields with excellent chemo ‐, regio ‐, and stereo ‐control, which significantly enlarge the chemical space of the optically active silicon‐stereogenic monohydrosilanes.

Topics & Concepts

StereocenterSilanesEnantioselective synthesisSilylationIntermolecular forceChemistryEnantiomerStereochemistrySiliconRhodiumOrganic chemistryCatalysisMoleculeSilaneOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions
Enantioselective Intermolecular C−H Silylation of Heteroarenes for the Synthesis of Acyclic Si‐Stereogenic Silanes | Litcius