Pd/Ming-Phos-Catalyzed Asymmetric Three-Component Arylsilylation of N -Sulfonylhydrazones: Enantioselective Synthesis of gem -Diarylmethine Silanes.
Bin YangKangning CaoGuofeng ZhaoJunfeng YangJunliang ZhangPublished in: Journal of the American Chemical Society (2022)
A Pd-catalyzed enantioselective three-component reaction of N -sulfonylhydrazones, aryl bromides, and silylboronic esters is developed, enabling the synthesis of chiral gem -diarylmethine silanes in high enantioselectivity with the use of a newly identified Ming-Phos . Compared with N -tosyl, the more easily decomposed N -mesitylsulfonyl is more suitable as the masking group of electron-rich hydrazone to improve the reaction efficiency. The reaction features a broad scope concerning both coupling partners, high enantioselectivity, and mild reaction conditions. The ready access to enantiomers and utility of this catalytic method are also presented.