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

被引：41
|
作者：
Niederer, Kyle A. [1 ]
Gilmartin, Philip H. [1 ]
Kozlowski, Marisa C. [1 ]
机构：
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19014 USA
来源：
ACS CATALYSIS | 2020年 / 10卷 / 24期
关键词：
oxidative coupling; phenol coupling; photocatalysis; tyrosine dimerization; cross-coupling; ELECTRON-TRANSFER; BIOMIMETIC SYNTHESIS; ARENE; DIMERS; OXYGENATION; BIPHENOLS; DIOXYGEN;
D O I：
10.1021/acscatal.0c04515
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
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.
引用
收藏
页码：14615 / 14623
页数：9
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