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Updated: Jun 11, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene
Brian M Casey1, Cynthia A Eakin, Jingliang Jiao
1Department of Chemistry, Lehigh University, Bethlehem, PA 18015, USA.
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.
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