N-picolinamides as ligands for Ullmann-type homocoupling reactions

Fehmi Damkaci; Esra Altay; Matthew Waldron; Michael A. Knopp; David Snow; Nicholas Massaro

doi:10.1016/j.tetlet.2013.11.111

N-picolinamides as ligands for Ullmann-type homocoupling reactions

Fehmi Damkaci, Esra Altay, Matthew Waldron, Michael A. Knopp, David Snow, Nicholas Massaro

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9 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	690-693
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2013.11.111
State	Published - Jan 15 2014
Externally published	Yes

Keywords

Aryl-aryl coupling
Copper catalyzed
Homocoupling
N-Picolinamides
Ullmann-type coupling

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title = "N-picolinamides as ligands for Ullmann-type homocoupling reactions",

abstract = "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.",

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AU - Damkaci, Fehmi

AU - Altay, Esra

AU - Waldron, Matthew

AU - Knopp, Michael A.

AU - Snow, David

AU - Massaro, Nicholas

PY - 2014/1/15

Y1 - 2014/1/15

N2 - 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.

AB - 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.

KW - Aryl-aryl coupling

KW - Copper catalyzed

KW - Homocoupling

KW - N-Picolinamides

KW - Ullmann-type coupling

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N-picolinamides as ligands for Ullmann-type homocoupling reactions

Abstract

Keywords

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