Palladium-catalyzed cycloaromatization of N-acyl-2-aminobiaryls, through a sequence of ortho CÀH bond activation/alkyne insertion/meta CÀH bond activation/alkyne insertion, was developed. An efficient synthesis of multiaryl-substituted naphthalenes, N-[2-(5,6,7,8-tetraarylnaphthalen-1yl)aryl]acetamides, was demonstrated using molecular oxygen as the sole oxidant. Furthermore, through Buchwald's synthetic protocol, two compounds were converted into corresponding fluorescent carbazoles in 30-40% yield by intramolecular CÀN bond formation.
We developed palladium-catalyzed oxidative coupling of olefins with N-acyl 2-aminobiaryls through a sequence of ortho C-H bond activation/alkene insertion/reductive elimination. Furthermore, we controlled the selectivity of mono- and bis-alkenylation products with the solvent effect. The developed protocol was promising for a broad substrate scope ranging from activated olefins with a wide variety of functional groups to unactivated olefins.
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