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

Abstract

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.

Topics & Concepts