Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.
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.
Casey
Brian M
BM
Department of Chemistry, Lehigh University, Bethlehem, PA 18015, USA.
Eakin
Cynthia A
CA
Jiao
Jingliang
J
Sadasivam
Dhandapani V
DV
Flowers
Robert A
RA