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.