Oxidative coupling of three different arenes and a thiophene derivative with various arylboronic acids was achieved with a [RhCl(C2H4)(2)](2)/ P[p-(CF3)C6H4](3) catalyst system. Commercially available 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO) was used as a stoichiometric oxidant. A 2-pyridyl group and an imine functional group served as ortho-directing groups to mediate the direct C-H arylation by a Rh complex. Moderate to excellent yields were obtained for the coupling reactions.
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