Department of Chemistry, Faculty of Science and Graduate School of Science, Tohoku University

　4,7’-Bibenzo[b]thiophenes bearing chlorine, bromine, iodine, and silicon atoms in one molecule was prepared as novel molecular scaffold. Three different aryl groups were site-selectively introduced by Suzuki-Miyaura cross coupling reactions and a C-H direct arylation while the trialkylsilyl group behaved as a protecting group (a molecular model is shown). Crystal structure of the precursor, (bromo)(chloro)(triisopropylsilyl)bibenzothiophene was analyzed to show directions of the Br—Cl axis and the side chain in the crystal.