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Photocatlytic oxidative coupling manuscript 02052020.pdf (19.56 MB)
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Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Non-Enzymatic, Catalytic Method for Coupling Tyrosine

preprint
submitted on 14.02.2020 and posted on 18.02.2020 by Kyle Niederer, Philip H. Gilmartin, Marisa Kozlowski
The first, oxidative photocatalytic method for phenol-phenol homo-coupling and cross-coupling is described and isolated yields of up to 97% are obtained. Measured oxidation potentials and computed nucleophilicity parameters are consistent with a nucleophilic attack of one partner onto the oxidized radical form of the other partner. Understanding of this model permitted development of cross-coupling reactions between nucleophilic phenols/arenes and easily oxidized phenols in high selectivity and efficiency. A highlight of this method is that one equivalent of each coupling partner is utilized. Building on these findings, the first non-enzymatic, catalytic method for coupling tyrosine was developed.

Funding

CHE1764298

R35 GM131902, RO1 GM112684

1S10RR023444, 1S10RR022442, CHE- 0840438, CHE-0848460, 1S10OD011980, CHE-1827457

DGE-1845298

History

Email Address of Submitting Author

marisa@sas.upenn.edu

Institution

University of Pennsylvania

Country

United States of America

ORCID For Submitting Author

0000-0002-4225-7125

Declaration of Conflict of Interest

No Conflict of interest

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