Ligand free open air copper(II) mediated aryl formamidation and amination of aryl halides

Ligand free open air copper(II) mediated aryl formamidation and amination of aryl halides

•Direct foramidation procedure of electron rich aromatic halides was developed.•Aryl amination was performed on open air without copper ligand.•Economical approach to aryl C–N bond formation.•Copper(II) sulfate mediated reactions. A simple synthetic procedure for direct formamidation and amination o...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 55; no. 9; pp. 1523 - 1527
Main Authors: Komati, Rajesh, Jursic, Branko S.
Format: Journal Article
Language:English
Published: Elsevier Ltd 26-02-2014
Subjects:
Anilines
Aromatic compounds
Aryl amination
Aryl dimethylamination
Aryl formamidation
Copper coupling
Formyl anilines
Halides
Ligands
Potassium carbonate
Tetrahedrons
Aryl amination
Anilines
Aryl dimethylamination
Formyl anilines
Copper coupling
Aryl formamidation
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Summary:•Direct foramidation procedure of electron rich aromatic halides was developed.•Aryl amination was performed on open air without copper ligand.•Economical approach to aryl C–N bond formation.•Copper(II) sulfate mediated reactions. A simple synthetic procedure for direct formamidation and amination of aryl halides mediated by copper(II) salts was developed in open air, without an external ligand in formamide with potassium carbonate as a base. This approach is particularly efficient when electron active aryl halides are used as substrates. In these cases almost quantitative formamidation was observed.
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.01.046