Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine
Kyle A. Niederer, Philip H. Gilmartin, Marisa C. Kozlowski
Abstract
The oxidative photocatalytic method for phenol-phenol homo-coupling and cross-coupling is described and isolated yields of 16-97% are obtained. Measured oxidation potentials and computed nucleophilicity parameters support a mechanism of nucleophilic attack of one partner onto the oxidized neutral radical form of the other partner. Understanding of this model permitted development of cross-coupling reactions between nucleophilic phenols/arenes and easily oxidized phenols with high selectivity and efficiency. A highlight of this method is that one equivalent of each coupling partner is utilized. Building on these findings, a non-enzymatic, catalytic method for coupling tyrosine was also developed.