Issue 53, 2022

Enantioselective synthesis of acyclic monohydrosilanes by steric hindrance assisted C–H silylation

Abstract

Herein, a rhodium-catalyzed desymmetrization of dihydrosilanes with heterocyclic compounds via intermolecular dehydrogenative C–H silylation is developed. The strategy tolerates a variety of thianaphthene and thiophene derivatives, giving rise to a wide range of silicon-stereogenic acyclic monohydrosilanes. Several rare skeletons featuring bis-silicon-stereogenic centers were also designed to enhance the library's diversity further. Preliminary mechanistic studies reveal that the surrounding spatial environment of the Si-center plays a crucial role in enabling intermolecular C–H silylation preferentially.

Graphical abstract: Enantioselective synthesis of acyclic monohydrosilanes by steric hindrance assisted C–H silylation

Supplementary files

Article information

Article type
Communication
Submitted
23 Apr 2022
Accepted
01 Jun 2022
First published
02 Jun 2022

Chem. Commun., 2022,58, 7388-7391

Enantioselective synthesis of acyclic monohydrosilanes by steric hindrance assisted C–H silylation

D. Mu, S. Pan, X. Wang, X. Liao, Y. Huang and J. Chen, Chem. Commun., 2022, 58, 7388 DOI: 10.1039/D2CC02307E

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