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

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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… Click to show full abstract

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.

Keywords: pyrans dicarbonyls; coupling dihydro; dihydro pyrans; cross dehydrogenative; dicarbonyls aryl; dehydrogenative coupling

Journal Title: Tetrahedron Letters
Year Published: 2019

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