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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Vydané v:	Tetrahedron Ročník 68; číslo 39; s. 8358 - 8366
Hlavní autori:	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
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	OXFORD Elsevier Ltd 30.09.2012 Elsevier
Predmet:	(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 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
ISSN:	0040-4020, 1464-5416
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Shrnutí:	(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]
Bibliografia:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2012.07.012