Chemo-, Regio-, and Stereoselective Synthesis of syn-Aryl Glycol Monoesters from Aryl Olefins with Hydrogen Peroxide Catalyzed by RuCl3

Abstract

Chemo-, regio-, and stereoselectivity have been achieved in the oxidations of aryl olefins. The aryl olefins were oxidized by 2 equivalents of H 2 O 2 in acetic acid, catalyzed by 0.02 equivalent of RuCl 3 , leading to the formations of syn-aryl glycol monoesters. As the reaction is concerted, both the regio-and stereoselectivity are excellent. In the presence of aliphatic C=C bonds, the aryl C=C bonds were selectively dioxygenated. This represents the first example of chemoselective dioxygenation of aryl C=C bonds.