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Pd/Ming-Phos-Catalyzed Asymmetric Three-Component Arylsilylation of N -Sulfonylhydrazones: Enantioselective Synthesis of gem -Diarylmethine Silanes.

Bin YangKangning CaoGuofeng ZhaoJunfeng YangJunliang Zhang
Published 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.
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