Convenient Synthesis of Dibenzo[<i>a</i>,<i>h</i>]anthracenes and Picenes via C–H Arylation of Acetophenones with Arenediboronates

Abstract

Abstract A new convenient method for the synthesis of dibenzo[a,h]anthracenes and picenes using ruthenium-catalyzed regioselective C–H arylation of aromatic ketones has been developed. Acetophenone derivatives and 1,4-benzenediboronates were coupled in 2:1 ratios to form p-terphenyl derivatives. Conversion of the acetyl group to an ethynyl group, followed by cycloaromatization provided the desired fused aromatic compounds. An organic field-effect transistor fabricated from one of these products gave moderate hole mobility.