Pd-catalyzed C-N bond formation with heteroaromatic tosylates.
A protocol for the palladium(0)-catalyzed amidation of heteroaromatic tosylates was successfully developed. The methodology proved to be effective for a variety of heteroaryl tosylates including the pyridine, pyrimidine, quinoline and quinoxaline ring systems. Successful carbon-nitrogen bond formation with these heteroaryl tosylates could be performed with a wide range of primary amides, oxazolidinones, lactams, anilines and indoles, including one cyclic urea. Moreover, this C-N bond forming reaction provided products with high structural diversity. The coupling reaction was also amenable to scale up applications.
Mantel
Mette L H
ML
The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
Lindhardt
Anders T
AT
Lupp
Daniel
D
Skrydstrup
Troels
T
D000577:Amides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature; D014105:Tosyl Compounds / Q000737:chemistry*
D000577:Amides; D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds; D014105:Tosyl Compounds; D010165:Palladium; D002244:Carbon; D009584:Nitrogen