N-picolinamides as ligands for Ullmann-type homocoupling reactions

The use of N-phenylpicolinamide (NPPA) as a ligand in Ullmann-type homocoupling reactions of aryl iodides and bromides in common solvents, such as DMF and MeCN has been successfully demonstrated at room temperature. In addition, this work provided the first example of the homocoupling of an aryl chl...

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Bibliographic Details
Published in:Tetrahedron letters 2014-01, Vol.55 (3), p.690-693
Main Authors: Damkaci, Fehmi, Altay, Esra, Waldron, Matthew, Knopp, Michael A., Snow, David, Massaro, Nicholas
Format: Article
Language:English
Subjects:
Aromatic compounds
Aryl–aryl coupling
Chemical reactions
Chlorides
Copper catalyzed
Halides
Homocoupling
Iodides
Ligands
N-Picolinamides
Solvents
Tetrahedrons
Ullmann-type coupling
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Summary:The use of N-phenylpicolinamide (NPPA) as a ligand in Ullmann-type homocoupling reactions of aryl iodides and bromides in common solvents, such as DMF and MeCN has been successfully demonstrated at room temperature. In addition, this work provided the first example of the homocoupling of an aryl chloride at 82°C, which is a relatively low temperature when compared to regular Ullmann reaction temperatures. Also, NPPA was successfully employed in base—and heat free Suzuki reactions, including electron rich and poor aryl halides with heteroarylboronic acids in moderate yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.11.111