Organo-Iodine(III)-Catalyzed Oxidative Phenol-Arene and Phenol-Phenol Cross-Coupling Reaction

Abstract

The direct oxidative coupling reaction has been an attractive tool for environmentally benign chemistry. Reported herein is that the hypervalent iodine catalyzed oxidative metal-free cross-coupling reaction of phenols can be achieved using Oxone as a terminal oxidant in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). This method features a high efficiency and regioselectivity, as well as functional-group tolerance under very mild reaction conditions without using metal catalysts. Criss-cross phenol: An organocatalytic intermolecular oxidative cross-coupling reaction of phenols uses a catalytic amount of an iodoarene with a stoichiometric amount of an inorganic oxidant. The reaction proceeds smoothly at room temperature, thereby enabling the efficient formation of biaryls from phenols without over-oxidation of the coupling products.