4.7 Article

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

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 53, Pages 7388-7391

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc02307e

Keywords

-

Funding

  1. National Natural Science Foundation of China [21825101]
  2. Hong Kong RGC [16300320]
  3. Guangdong Basic and Applied Basic Research Foundation [2019A1515011641, 2021A1515110352, 2022A1515010916]
  4. Shenzhen Science and Technology Innovation Commission [SGDX2019081623241924, KCXFZ20201221173404013]

Ask authors/readers for more resources

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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available