Catalytic Asymmetric Dehydrogenative Si-H/N-H Coupling: Synthesis of Silicon-Stereogenic Silazanes
Meng-Meng Liu, Yankun Xu and Chuan He*
*Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China,
Email: hec
sustech.edu.cn
M.-M. Liu, Y. Xu, C. He, J. Am. Chem. Soc., 2023, 145, 11727-11734.
DOI: 10.1021/jacs.3c02263
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Abstract
A catalytic dehydrogenative coupling of dihydrosilanes with anilines enables a highly enantioselective synthesis of silicon-stereogenic silazanes in excellent yields and stereoselectivities. In addition, straightforward transformations of the enantioenriched silazanes deliver various chiral silane compounds in a stereospecific fashion.
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Enantioselective Construction of Si-Stereogenic Silazanes
In an argon-atmosphere glovebox, dihydrosilane substrate (0.11 mmol) and anilines substrate (0.1 mmol) were added to a solution of [Rh(cod)Cl]2 (1.0 mg, 2 mol%) and ligand (2.4 mg, 4.5 mol%) in toluene (0.5 mL), the oven-dried 5 mL microwave reaction tube was sealed and removed from the glovebox, the mixture was stirred at room temperature for suitable time. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash chromatography to give the desired product. The enantiomeric excess was determined by chiral HPLC analysis.
J. Zhu, S. Chen, C. He, J. Am. Chem. Soc., 2021, 143, 5301-5307.
Key Words
ID: J48-Y2023
