Organic Chemistry Laboratory, Nagoya University

Kenji Mochida, Katsuaki Kawasumi, Yasutomo Segawa, and Kenichiro Itami

J. Am .Chem .Soc. 2011, ASAP. DOI: 10.1021/ja202975w

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We have discovered that the combination of Pd(OAc)2/o-chloranil can catalyze the direct C–H bond arylation of polycyclic aromatic hydrocarbons (PAHs) with arylboroxins that occurs selectively at the K-region. The sequential integration of Pd-catalyzed direct arylation of PAHs and FeCl3-mediated cyclodehydrogenation is effective in rapidly extending a parent PAH π-system with high directionality.