Reductive desymmetric silylation of biaryl bis(triflates) enabled by a chiral nickel/picolinamide complex

手性镍/吡啶甲酰胺络合物催化的联芳基双(三氟甲磺酸酯)的还原性不对称硅烷化反应。

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Abstract

Given the importance of organosilicons and atropisomerism, there is a fundamental need to develop new methods to synthesize axially chiral biaryl silanes. By use of an easily accessible chiral picolinamide as a ligand and inexpensive nickel as a catalyst, we realize a desymmetric silylation of prochiral biaryl bis(triflates) with silyl chlorides under net reductive conditions. This cross-electrophile reaction offers a new approach to preparing highly enantioenriched C (1)-symmetric axially chiral platform molecules, which incorporate both a silane and a triflate moiety as two distinct docking sites for various downstream derivatizations.

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