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

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2022)

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摘要
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.
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Asymmetric Catalysis, Dehydrogenative Coupling, Rhodium, Silylation, Stereogenic Silanes
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