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Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine.

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.

SUBMITTER: Niederer KA

PROVIDER: S-EPMC8078885 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine.

Niederer Kyle A KA Gilmartin Philip H PH Kozlowski Marisa C MC

ACS catalysis 20201125 24

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 ...[more]

PMID: 33927912

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