Chemistry Letters, Vol.40, No.3, 300-302, 2011
Convenient Synthesis of Dibenzo[a,h]anthracenes and Picenes via C-H Arylation of Acetophenones with Arenediboronates
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.