Reductive Cross-Coupling between Arylaldehydes and (Hetero)aryl Electrophiles Using Silylboronate Reductant

Graphical Abstract

This manuscript describes a catalytic reductive cross-coupling between arylaldehydes and aryl electrophiles using silylboronate as a terminal reductant. The reaction involves a copper-catalyzed silylboration of aldehydes affording the O-borylated α-silyl alcohols followed by the nucleophilic aromatic substitution reaction with aryl electrophiles. This protocol offers a new opportunity to access 1,1-diarylmethanol derivatives without rare-metals and highly basic organometallic reagents.

Abstract

A catalytic reductive cross-coupling between arylaldehydes and aryl electrophiles using a silylboronate as a terminal reductant is described. The reaction involves a copper-catalyzed silylboration of aldehydes affording the O-borylated α-silyl alcohols followed by a nucleophilic aromatic substitution reaction with aryl electrophiles. This protocol offers a new opportunity to access 1,1-diarylmethanol derivatives without rare metals or highly basic organometallic reagents.