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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 Chemie International Edition79 citationsDOI

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 forceChemistryStereochemistrySiliconEnantiomerOrganic chemistryCatalysisMoleculeSilaneOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions
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