Synthesis of polyaromatic hydrocarbons from bis(biaryl)diynes: Large PAHs with low Clar sextets

Abstract

A new synthesis of large polyaromatic hydrocarbons (PAHs) with low Clar sextets is reported (see figure). The synthetic protocol involves starting bis(biaryl)diynes, which undergo initial PtCl2-catalyzed aromatizations, and subsequent 2,3-dichloro-5,6-dicyano benzoquinone (DDQ) oxidation. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.