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Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

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 alpha-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.

SUBMITTER: Casey BM

PROVIDER: S-EPMC2898135 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

Casey Brian M BM Eakin Cynthia A CA Jiao Jingliang J Sadasivam Dhandapani V DV Flowers Robert A RA

Tetrahedron 20091201 52

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 alpha-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 ...[more]

PMID: 20625455

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Corrigendum to Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

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