Double dehydrogenation of carbocyclic β-dicarbonyl compounds: Koser’s reagent can do what iodine(V) reagents can

Abstract

Koser’s reagent is found to be effective in the oxidative double dehydrogenation of various carbocyclic β-dicarbonyl compounds, which constitutes the first example on dehydrogenation reactivity of hypervalent iodine(III) reagents for carbocyclic carbonyl compounds. DFT calculations reveal that the rate-determining step is the electrophilic addition of PhI+OH onto enolate of monodehydrogenated product.