Palladium-catalyzed intramolecular coupling of arenes and unactivated alkanes in air

Palladium-catalyzed arene-alkane coupling reactions are described that create a new C(sp(2))-C(sp(3)) bond between an azole ring and an unactivated methyl substituent. The reactions employ a simple, readily available palladium catalyst, exhibit high regioselectivity with respect to both the azole and the alkane moieties, and can be performed in an open flask using air as the terminal oxidant.