Cross-dehydrogenative coupling of 3,6-dihydro-2H-pyrans with 1,3-dicarbonyls and aryl moieties

Abstract An indium-catalyzed oxidative C H alkylation and arylation of 4-substituted 3,6-dihydro-2H-pyrans (DHPs) using dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as the oxidant has been developed. The mild and modular cross-dehydrogenative coupling reaction exhibited a broad scope with respect to both DHPs and nucleophilic 1,3-dicarbonyl moieties as well as aryl rings, rapidly providing 2,4-disubstituted DHPs bearing diverse patterns of functionalities at the α position.