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Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst
Author(s) -
Han Sheng,
Cheng Ying,
Liu Shanshan,
Tao Chaofu,
Wang Aiping,
Wei Wanguo,
Yu Han,
Wei Yongge
Publication year - 2021
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.202013940
Subject(s) - catalysis , azobenzene , chemistry , hydrogen peroxide , oxide , stoichiometry , molybdenum , combinatorial chemistry , solvent , molybdenum oxide , aniline , organic chemistry , polymer chemistry , molecule
Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C 4 H 9 ) 4 ] 2 [Mo 6 O 19 ] ( 1 ), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.