Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.
CuI-catalyzed coupling reaction of electron-deficient aryl iodides with aliphatic primary amines occurs at 40 degrees C under the promotion of N-methylglycine. Using l-proline as the promoter, coupling reaction of aryl iodides or aryl bromides with aliphatic primary amines, aliphatic cyclic secondary amines, or electron-rich primary arylamines proceeds at 60-90 degrees C; an intramolecular coupling reaction between aryl chloride and primary amine moieties gives indoline at 70 degrees C; coupling reaction of aryl iodides with indole, pyrrole, carbazole, imidazole, or pyrazole can be carried out at 75-90 degrees C; and coupling reaction of electron-deficient aryl bromides with imidazole or pyrazole occurs at 60-90 degrees C to provide the corresponding N-aryl products in good to excellent yields. In addition, N,N-dimethylglycine promotes the coupling reaction of electron-rich aryl bromides with imidazole or pyrazole to afford the corresponding N-aryl imidazoles or pyrazoles at 110 degrees C. The possible action of amino acids in these coupling reactions is discussed.
Zhang
Hui
H
Department of Chemistry, Fudan University, Shanghai 200433, China.
Cai
Qian
Q
Ma
Dawei
D
D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D006219:Halogens / Q000737:chemistry*; D007202:Indicators and Reagents; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry; D013696:Temperature
D000588:Amines; D000596:Amino Acids; D001555:Benzene Derivatives; D006219:Halogens; D007202:Indicators and Reagents; D007454:Iodides; D003300:Copper; C073870:cuprous iodide; D011392:Proline; D005998:Glycine