Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene |
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Authors: | Brian M. Casey |
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Affiliation: | Department of Chemistry, Lehigh University, Bethlehem, PA 18015, USA |
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Abstract: | This report describes the scope and mechanism of the solvent-dependent, chemoselective oxidative coupling of 1-aryl-1,3-dicarbonyls with styrene using Ce(IV) reagents. Dihydrofuran derivatives are obtained when reactions are performed in methanol whereas α-tetralones can be selectively synthesized in acetonitrile and methylene chloride. Mechanistic studies are consistent with the rate of solvent-assisted deprotonation of a radical cation intermediate playing an integral role in the selective formation of products. |
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