Arynes, diaryliodonium salts and azine N-oxides in transition metal-free electrophilic N-arylation

The main approach to the synthesis of aromatic and heteroaromatic amines is based on palladium- and copper-catalyzed N-arylation reactions. Although these methods are highly efficient and provide extensive opportunities for the synthesis of (het)arylamines with various structures and properties, the...

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Bibliographic Details
Published in:Russian chemical reviews 2018-03, Vol.87 (3), p.272-301
Main Authors: Bugaenko, Dmitry I., Karchava, Alexander V., Yurovskaya, Marina A.
Format: Article
Language:English
Subjects:
Amines
Catalysts
Chemical reactions
Organic compounds
Palladium
Synthesis
Transition metals
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Summary:The main approach to the synthesis of aromatic and heteroaromatic amines is based on palladium- and copper-catalyzed N-arylation reactions. Although these methods are highly efficient and provide extensive opportunities for the synthesis of (het)arylamines with various structures and properties, they have some limitations related to the catalysts used and reaction conditions. This review addresses alternative approaches to N-(het)arylation that have been extensively developed in the past decade and are based on the use of arynes, diaryliodonium salts and azine N-oxides as electrophilic (het)arylating agents. Because of mild reaction conditions and no need for catalysts and strong bases, these N-(het)arylation methods are attractive for various synthetic applications and open up new possibilities for the preparation of valuable organic compounds inaccessible via traditional catalytic methods. The attention is focussed on publications of the last decade. The bibliography includes 112 references.
ISSN:0036-021X
1468-4837
DOI:10.1070/RCR4781