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

An oxidative photocatalytic method for phenol–phenol homo- 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 fo...

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Published inACS catalysis Vol. 10; no. 24; pp. 14615 - 14623
Main Authors Niederer, Kyle A, Gilmartin, Philip H, Kozlowski, Marisa C
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 18.12.2020
Subjects
cross-coupling
oxidative coupling
phenol coupling
tyrosine dimerization
photocatalysis
Oxidative coupling
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Summary:An oxidative photocatalytic method for phenol–phenol homo- 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. Our understanding of this model permitted the 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 nonenzymatic, catalytic method for coupling tyrosine was also developed.
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ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.0c04515