Biomimetic Aerobic Removal of p-Hydroxyphenyl Group on Nitrogen or Oxygen Using Iron Phthalocyanine Catalyst

Abstract

A biomimetic dearylation protocol was developed for removing the p-hydroxyphenyl group from nitrogen- or oxygen-containing functionalities in an aqueous medium using a FePc(CO2H)8 catalyst and molecular oxygen as the terminal oxidant. This method removes a p-hydroxyphenyl moiety from amides, ethers, and carboxylic acids. Despite involving an oxidative process, the reaction exhibits excellent chemoselectivity and tolerates various oxidant-sensitive functional groups. Furthermore, the protocol is highly compatible with gram-scale synthesis. In addition to its synthetic utility, this environmentally benign methodology relies on an iron catalyst and molecular oxygen.