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A Biomimetic Catalytic Aerobic Functionalization of Phenols
Author(s) -
Esguerra Kenneth Virgel N.,
Fall Yacoub,
Lumb JeanPhilip
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201311103
Subject(s) - phenols , catalysis , chemistry , surface modification , combinatorial chemistry , aromaticity , organic chemistry , molecule
The importance of aromatic CO, CN, and CS bonds necessitates increasingly efficient strategies for their formation. Herein, we report a biomimetic approach that converts phenolic CH bonds into CO, CN, and CS bonds at the sole expense of reducing dioxygen (O 2 ) to water (H 2 O). Our method hinges on a regio‐ and chemoselective copper‐catalyzed aerobic oxygenation to provide ortho ‐quinones. ortho ‐Quinones are versatile intermediates, whose direct catalytic aerobic synthesis from phenols enables a mild and efficient means of synthesizing polyfunctional aromatic rings.