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O 2 ‐mediated dehydrogenative amination of phenols
Author(s) -
LouillatHabermeyer MarieLaure,
Jin Rongwei,
Patureau Frederic W.
Publication year - 2015
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.201500089
Subject(s) - amination , aniline , reactivity (psychology) , chemistry , substrate (aquarium) , phenols , cumene , halide , combinatorial chemistry , organic chemistry , catalysis , medicine , oceanography , alternative medicine , pathology , geology
A method was developed for the direct dehydrogenative construction of CN bonds between unprotected phenols and a series of cyclic anilines without resorting to any kind of metal activation of either substrate and without the use of halides. The resulting process relies on the exclusively organic activation of molecular oxygen and the subsequent oxidation of the aniline substrate. This allows the coupling of ubiquitous phenols, thus furnishing aminophenols through an atom‐economical and most sustainable dehydrogenative amination method. This new reactivity, which relies on the intrinsic organic reactivity of cumene in what can be seen as a modified Hock activation process of oxygen, is expected to have a large impact on the formation of CN bonds in organic synthesis.