Organocatalytic oxidative dehydrogenation of aromatic amines for the preparation of azobenzenes under mild conditions

(Diacetoxyiodo)benzene used as stoichiometrically and catalytically in the preparation of azobenzenes under mild reaction conditions was developed. The metal-free oxidation systems demonstrated wide substituents tolerance, alkyls, halogens, and several versatile functional groups, such as amino, eth...

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Veröffentlicht in:Tetrahedron Jg. 68; H. 39; S. 8358 - 8366
Hauptverfasser: Ma, Hengchang, Li, Wenfeng, Wang, Jian, Xiao, Guanghai, Gong, Yuan, Qi, Chunxuan, Feng, Yunpeng, Li, Xiufang, Bao, Zhikang, Cao, Wei, Sun, Qiangsheng, Veaceslav, Caraus, Wang, Feng, Lei, Ziqiang
Format: Journal Article
Sprache:Englisch
Veröffentlicht: OXFORD Elsevier Ltd 30.09.2012
Elsevier
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ISSN:0040-4020, 1464-5416
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Abstract (Diacetoxyiodo)benzene used as stoichiometrically and catalytically in the preparation of azobenzenes under mild reaction conditions was developed. The metal-free oxidation systems demonstrated wide substituents tolerance, alkyls, halogens, and several versatile functional groups, such as amino, ethynyl, and carboxyl substituents are compatible well, and the corresponding products could be formed with good to excellent yields. In this disclosed method, the more large scale formation of azo compounds also could be carried out successfully. Of note that 3-ethynylbenzenamine applied as a very useful cross dehydrogenative partner, which coupled with different anilines, providing asymmetrical azo compounds with acceptable yields in one step under very mild reaction conditions. [Display omitted]
AbstractList (Diacetoxyiodo)benzene used as stoichiometrically and catalytically in the preparation of azobenzenes under mild reaction conditions was developed. The metal-free oxidation systems demonstrated wide substituents tolerance, alkyls, halogens, and several versatile functional groups, such as amino, ethynyl, and carboxyl substituents are compatible well, and the corresponding products could be formed with good to excellent yields. In this disclosed method, the more large scale formation of azo compounds also could be carried out successfully. Of note that 3-ethynylbenzenamine applied as a very useful cross dehydrogenative partner, which coupled with different anilines, providing asymmetrical azo compounds with acceptable yields in one step under very mild reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
(Diacetoxyiodo)benzene used as stoichiometrically and catalytically in the preparation of azobenzenes under mild reaction conditions was developed. The metal-free oxidation systems demonstrated wide substituents tolerance, alkyls, halogens, and several versatile functional groups, such as amino, ethynyl, and carboxyl substituents are compatible well, and the corresponding products could be formed with good to excellent yields. In this disclosed method, the more large scale formation of azo compounds also could be carried out successfully. Of note that 3-ethynylbenzenamine applied as a very useful cross dehydrogenative partner, which coupled with different anilines, providing asymmetrical azo compounds with acceptable yields in one step under very mild reaction conditions.
(Diacetoxyiodo)benzene used as stoichiometrically and catalytically in the preparation of azobenzenes under mild reaction conditions was developed. The metal-free oxidation systems demonstrated wide substituents tolerance, alkyls, halogens, and several versatile functional groups, such as amino, ethynyl, and carboxyl substituents are compatible well, and the corresponding products could be formed with good to excellent yields. In this disclosed method, the more large scale formation of azo compounds also could be carried out successfully. Of note that 3-ethynylbenzenamine applied as a very useful cross dehydrogenative partner, which coupled with different anilines, providing asymmetrical azo compounds with acceptable yields in one step under very mild reaction conditions. [Display omitted]
Author Qi, Chunxuan
Wang, Jian
Li, Wenfeng
Xiao, Guanghai
Sun, Qiangsheng
Cao, Wei
Ma, Hengchang
Lei, Ziqiang
Feng, Yunpeng
Gong, Yuan
Wang, Feng
Bao, Zhikang
Li, Xiufang
Veaceslav, Caraus
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Issue 39
Keywords Organocatalytic
Amine
(Diacetoxyiodo)benzene
Azo
POLYMERS
AZO-COMPOUNDS
EFFICIENT METHOD
O-IODOXYBENZOIC ACID
HYPERVALENT IODINE
NITRO-COMPOUNDS
SYMMETRIC HYDRAZO COMPOUNDS
CHEMISTRY
DERIVATIVES
IBX
Diacetoxyiodobenzene
Catalytic reaction
Acetylenic compound
Mild operating conditions
Organocatalyst
Aniline derivatives
Azo compound
Dehydrogenation
Halogen compound
Benzenic compound
Oxidation
Large scale
Chemical synthesis
Arylamine
Azobenzene
Functional group
Language English
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Snippet (Diacetoxyiodo)benzene used as stoichiometrically and catalytically in the preparation of azobenzenes under mild reaction conditions was developed. The...
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SubjectTerms (Diacetoxyiodo)benzene
Acceptability
Amine
aromatic amines
Asymmetry
Azo
Azo compounds
benzene
Catalysis
Catalysts: preparations and properties
chemical structure
Chemistry
Chemistry, Organic
Compatibility
Dehydrogenation
Exact sciences and technology
General and physical chemistry
Halogens
Noncondensed benzenic compounds
Organic chemistry
Organocatalytic
oxidation
Physical Sciences
Preparations and properties
Science & Technology
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Tolerances
Title Organocatalytic oxidative dehydrogenation of aromatic amines for the preparation of azobenzenes under mild conditions
URI https://dx.doi.org/10.1016/j.tet.2012.07.012
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