Direct arylation of polycyclic aromatic hydrocarbons through palladium catalysis

Kenji Mochida; Katsuaki Kawasumi; Yasutomo Segawa; Kenichiro Itami

doi:10.1021/ja202975w

Direct arylation of polycyclic aromatic hydrocarbons through palladium catalysis

J Am Chem Soc. 2011 Jul 20;133(28):10716-9. doi: 10.1021/ja202975w. Epub 2011 Jun 23.

Authors

Kenji Mochida¹, Katsuaki Kawasumi, Yasutomo Segawa, Kenichiro Itami

Affiliation

¹ Department of Chemistry, Graduate School of Science, Nagoya University, Nagoya 464-8602, Japan.

PMID: 21699210
DOI: 10.1021/ja202975w

Abstract

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 FeCl(3)-mediated cyclodehydrogenation is effective in rapidly extending a parent PAH π-system with high directionality.