N-picolinamides as ligands for Ullmann-type homocoupling reactions

作者：Damkaci Fehmi^*; Altay Esra; Waldron Matthew; Knopp Michael A; Snow David; Massaro Nicholas

来源：Tetrahedron Letters, 2014, 55(3): 690-693.

DOI：10.1016/j.tetlet.2013.11.111

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

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 degrees 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.

• 出版日期2014-1-15