An efficient iron-catalyzed oxidative unsymmetrical biphenol coupling in 1,1,1,3,3,3-hexafluoropropoan-2-ol (HFIP) that proceeds via a chelated radical-nucleophile coupling mechanism was developed. Based on mechanistic studies, electrochemical methods, and DFT calculations, we suggest a general model that enables prediction of the feasibility of cross-coupling for a given pair of phenols.
Libman, A.; Shalit, H.; Vainer, Y.; Narute, S.; Kozuch, S.; Pappo, D., Synthetic and Predictive Approach to Unsymmetrical Biphenols by Iron-Catalyzed Chelated Radical–Anion Oxidative Coupling. Journal of the American Chemical Society 2015.