Selective Synthesis of (Benzyl)biphenyls by Successive Suzuki-Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl Acetate under Air Atmosphere.

Abstract

An efficient Pd-catalyzed cross-coupling reaction of phenylboronic acids and benzyl carbonates was developed, producing diarylmethanes. Benzyl acetates could also be used as coupling partners instead of benzyl carbonates, affording diarylmethanes in comparable yields. This reaction can be conducted under air atmosphere without any care for moisture and oxygen. The ester function showed an intermediate reactivity between chloro and bromo groups. This property facilitated the selective synthesis of diverse (benzyl)biphenyls by successive Suzuki–Miyaura coupling reactions using bromo- and chloro-substituted benzyl esters with two types of boronic acids.