Journal
CHEMICAL COMMUNICATIONS
Volume 58, Issue 53, Pages 7388-7391Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc02307e
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Funding
- National Natural Science Foundation of China [21825101]
- Hong Kong RGC [16300320]
- Guangdong Basic and Applied Basic Research Foundation [2019A1515011641, 2021A1515110352, 2022A1515010916]
- Shenzhen Science and Technology Innovation Commission [SGDX2019081623241924, KCXFZ20201221173404013]
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In this study, a rhodium-catalyzed desymmetrization of dihydrosilanes with heterocyclic compounds via intermolecular dehydrogenative C-H silylation was developed. The strategy demonstrated tolerance towards a variety of thianaphthene and thiophene derivatives, leading to the synthesis of a wide range of silicon-stereogenic acyclic monohydrosilanes. Additionally, rare skeletons featuring bis-silicon-stereogenic centers were designed to further enhance the diversity of the compound library. Preliminary mechanistic studies revealed the crucial role of the spatial environment surrounding the Si-center in enabling intermolecular C-H silylation preferentially.
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.
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