Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 3, Issue 4, Pages 759-766Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200700370
Keywords
aromatic compounds; C-C coupling; cyclodehydrogenation; hexabenzocoronene; hexaphenylbenzene
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A series of symmetrically and unsymmetrically substituted hexaphenyl benzene (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 FeCl3 gave the corresponding hexabenzocoronene (HBC) derivative in good yield.
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