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Short Synthesis of Alkyl-Substituted Acenes Using Carbonyl-Directed C–H and C–O Functionalization

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posted on 03.08.2012 by Daiki Matsumura, Kentaroh Kitazawa, Seiya Terai, Takuya Kochi, Yutaka Ie, Masashi Nitani, Yoshio Aso, Fumitoshi Kakiuchi
A convenient method for the synthesis of tetraalkylanthracenes and -pentacenes by means of ruthenium-catalyzed regioselective C–H alkylation of the corresponding acenequinones was developed. Dialkyldiarylpentacene was also synthesized using chemoselective tandem C–H alkylation/C–O arylation of dimethoxypentacenequinone. It was suggested that a tetraalkylpentacene is stable under air in the dark and possesses an appropriate HOMO level as active material for p-type organic field-effect transistors (OFETs).