N-hydroxyimides as efficient ligands for the copper-catalyzed N-arylation of pyrrole, imidazole, and indole.
An experimentally simple, efficient, and inexpensive catalyst system was developed for the N-arylation of pyrroles, indoles, and imidazole with aryl and heteroaryl iodides, bromides, and chlorides by applying CuI as catalyst, N-hydroxysuccinimide (L1), N-hydroxymaleimide (L2), or N-hydroxyphthalimide (L3) as ligand, CH3ONa as base, and DMSO as solvent. A variety of functional groups are tolerated in the reaction, including those that are not compatible with Pd-catalyzed amidation methodology.
Ma
Heng-Chang
HC
Department of Chemistry, Zhejiang University, Hangzhou, China.
Jiang
Xuan-Zhen
XZ
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D007093:Imidazoles; D007094:Imides; D007211:Indoles; D007454:Iodides; D008024:Ligands; D011758:Pyrroles; D003300:Copper; C073870:cuprous iodide