Journal
TETRAHEDRON
Volume 68, Issue 39, Pages 8358-8366Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.07.012
Keywords
Azo; (Diacetoxyiodo)benzene; Organocatalytic; Amine
Categories
Funding
- National Natural Science Foundation of China [21174114, 21163016, 1010RJZA024]
- Young Teacher Research Foundation of Northwest Normal University [NWNU-LKQN-08-8, NWNU-kjcxgc-03-73, NWNU-kjcxgc-03-63]
- Key Laboratory of Eco-Environment-Related Polymer Materials (Northwest Normal University), Ministry of Education
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(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.
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