A series of symmetrically and unsymmetrically substituted hexaphenylbenzene (HPB) analogues were efficiently synthesized by using a sterically hindered Suzuki-Miyaura cross-coupling reaction of arylboronic acids with 1,4-diiodo-2,3,5,6-tetraarylbenzenes under our optimized reaction conditions. The 1,4-diiodo-2,3,5,6-tetraarylbenzenes can be readily prepared by using a one-pot Hart reaction. Oxidative cyclodehydrogenation of the dibromo derivative with FeCl(3) gave the corresponding hexabenzocoronene (HBC) derivative in good yield.
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Yang et al. (2008) studied this question.
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