Oxidation of phenols with o-iodoxybenzoic acid

CHED 310

Jason Phillips, jphillips20@mail.csuchico.edu, Chris Taylor, taychr@gmail.com, and Jinsong Zhang, jzhang2@csuchico.edu. Department of Chemistry and Biochemistry, California State University, Chico, 400 West First St., Chico, CA 95929
Hypervalent iodine compounds (e.g. o-iodoxybenzoic acid, IBX) have been widely utilized as oxidation reagents because of their efficiency, availability, and mild reaction conditions. Regioselective oxidation of substituted phenols utilizing IBX and polymer-supported IBX will be discussed. The resulting ortho-quinone can undergo an inverse electron demand hetero-Diels-Alder reaction with a variety of dienophiles in situ to generate a 1,4-benzodioxane scaffold, which is a core structure for a number of natural products.