☆ 4.8 Review

Silicon-Stereogenic Monohydrosilane: Synthesis and Applications

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Enantioselective Synthesis of Silicon-Stereogenic Monohydrosilanes by Rhodium-Catalyzed Intramolecular Hydrosilylation

Yu-Hao Huang et al.

Summary: This study demonstrated an asymmetric synthesis method for monohydrosilanes via intramolecular hydrosilylation strategy, with high diastereo-, regio-, and enantioselectivities, including chiral oxasilacycles. The catalyst loading could be reduced to 0.1 mol %, making it one of the most efficient methods for accessing chiral monohydrosilanes. Mechanistic studies suggest a Chalk-Harrod mechanism for the Rh-catalyzed intramolecular asymmetric hydrosilylation reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Enantioselective C-H Functionalization toward Silicon-Stereogenic Silanes

Wei Yuan et al.

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Rhodium hydride enabled enantioselective intermolecular C-H silylation to access acyclic stereogenic Si-H

Kun An et al.

Summary: This study presents a method for enantioselective intermolecular C-H bond silylation, leading to the construction of a wide array of acyclic stereogenic Si-H compounds under simple and mild reaction conditions. The results highlight opportunities in converting simple arenes into value-added stereogenic silicon compounds.

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

Shuyou Chen et al.

Summary: In this study, we report a new method for the synthesis of acyclic silanes bearing a silicon-stereogenic center using a rhodium-catalyzed intermolecular dehydrogenative Si-H/C-H cross-coupling reaction. The method shows good yields and stereo-control, significantly enlarging the chemical space of optically active silicon-stereogenic monohydrosilanes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Wenxin Lu et al.

Summary: This study presents the catalytic sequential hydrosilylation of 1,3-enynes and 1,4-enynes promoted by cobalt complexes derived from bisphosphines. The reactions resulted in the formation of enantioenriched cyclic alkenylsilanes with simultaneous construction of a carbon-stereogenic center and a silicon-stereogenic center. The functionalization of these chiral silanes provides access to a variety of difficult-to-access chiral building blocks.

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Rhodium-Catalyzed Synthesis of Chiral Monohydrosilanes by Intramolecular C-H Functionalization of Dihydrosilanes

Wenpeng Ma et al.

Summary: A Rh-catalyzed desymmetrization of dihydrosilanes under simple and mild conditions provides easy access to a range of chiral monohydrosilanes with good yields and excellent enantioselectivities (up to >99% ee). These monohydrosilanes serve as a useful platform to access stereogenic silicon compounds and probe silicon stereochemistry.

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Article Chemistry, Organic

Asymmetric Synthesis of Silicon-Stereogenic Monohydrosilanes by Dehydrogenative C-H Silylation

Wei Yuan et al.

Summary: This method enables the synthesis of various asymmetrically trisubstituted 1H-benzosiloles and 1H-benzosilolome-tallocenes with good yields and excellent chemo-, regio-, and stereocontrol. The resulting silicon-stereogenic 1H-benzosilole compounds exhibit bright blue fluorescence and CPL signals, making them attractive to materials science practitioners.

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Jia-Le Xie et al.

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Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles

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Catalytic Asymmetric Synthesis of Silicon-Stereogenic Dihydrodibenzosilines: Silicon Central-to-Axial Chirality Relay

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Long Zheng et al.

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