Patent ID: 6867298

Claim:
A method represented by Scheme 2: wherein X represents I, Br, Cl, alkylsulfonate, or arylsulfonate; Z represents optionally substituted aryl, heteroaryl or alkenyl; (N-containing-heterocycle)-H represents optionally substituted pyrazole, pyrrole, tetrazole, imidazole, indazole, 1,2,3-triazole, 1,2,4-triazole, indole, carbazole, benzotriazole, benzimidazole, guanine, purine, adenine, xanthine, 8-azaadenine, 8-azoapoxanthine, uracil, 6-azauracil, cytocine, thymine, 6-azathymine, uric acid, benzoylene urea, 4-(3H)-pyrimidone, pyridone, 1(2H)-phthalazinone, 1,2,3-benzotriazine-4(3H)-one, benzimidazolinone, 2-benzoxazolinone, thymidine, uridine, (−)-inosine, 1H-1,2,3,5-diazadiphosphole, 1H-1,2,3-azadiphosphole, 1H-1,2,4-azadiphosphole, 1H-1,2,4-diazaphosphole, 1H-1,2,3-diazaphosphole, 1H-1,3,2-diazaphosphole, 1H-1,2-azadiphosphole, 1H-1,3-azadiphosphole, 1H-1,2,3,4-triazaphosphole, 1H-1,2,3,5-dithiadiazolidene, 1H-1,3,2,4-dithiadiazolidene, 1,3,2-oxathiazole, 3H-1,2,3-oxathiazole, 1,3,2-dithiazole, 1H-1,2-azaborole, pentazole, 3H-1,2,3-dioxazole, 2H-1,2,3-oxadiazine, 2H-1,2,4-oxadiazine, 2H-1,2,5-oxadiazine, 2H-1,2,6-oxadiazine, 2H-1,2,3-thiadiazine, 2H-1,2,4-thiadiazine, 2H-1,2,5-thiadiazine, 2H-1,2,6-thiadiazine, 2H-1,2-thiazine, 1,3,5,2,4,6-trithiatriazine, 2H-1,2,4,5-oxatriazine, 4H-1,3,2,4-dithiadiazine, 2H, 4H-1,3,2,5-dioxadiazine, 2H-1,5,2,4-dioxadiazine, 2H-1,2,4,6-thiatriazine, 2H-1,2,4,5-thiatriazine, 4H-1,3,2-dithiazane, 4H-1,3,2-dioxazine, 2H-1,5,2-dioxazine, 1,3,4-dithiazane, 4H-1,3,2-oxathiazine, 2H, 4H-1,3,2-oxathiazine, 2H, 4H-1,5,2-oxathiazine, 2H-1,2-diazepine, 2H-1,3-diazepine, 2H-1,4-diazepine, 2H-1,2,5-triazepine, 2H-1,3,5-triazepine, 2H-1,2,4-triazepine, 1H-azepine, 2H-1,2,3,5-tetrazepine, 2H-1,2,4,6-tetrazepine, 2H-1,2,4,5-tetrazepine, 2H-1.5.2.4-dithiadiazepine, 1,3,5,2,4,7-trithiatriazepine, 1,3,5,2,4-trithiadiazepine, pentahydro-1,3,5,2,4,6,8-trithiatetrazocine, 2H,6H-1,5,2,4,6,8-dithiatetrazocine, 2H-1,2,5-oxadiazocine, 2H-1,2,6-oxadiazocine, 2H-1.2-oxazocine, 2H-1,2-thiazocine, 4H-1,2,5-thiadiazocine, 4H-1,2,6-thiadiazocine, 5H-[1,2,4]-thiadiazolo[1,5-b][1,2,4]oxathiazole, triazolothiadiazole, thienothiadiazole, 1H-imidazo[1,2-a]imidazole, 4H-furo[3,2-b]pyrrole[3,4-b], 1H-pyrrolopyrazole, 1H-[2,3-d]thienopyrazole, 1H-[3,4-d]thienopyrazole, 1H-[2,3-c]thienopyrazole, 1H-[3,4-c]thienopyrazole, 1H-1,3-benzazaphosphole, 1H-benzazepine, 2H-2-benzazepine, 1H-1,3-benzodiazepine, 1H-1,4-benzodiazepine, 1H-1,5-benzodiazepine, 1H-1,2,4-benzotriazepine, 1H-1,2,5-benzotriazepine, 1H-1,3,4-benzotriazepine, or 3H-3-benzazepine; catalyst consists essentially of a copper atom or ion, and at least one ligand selected from the group consisting of optionally substituted phenol 1-naphthol, alkyl amine, 1,2-diamine, 1,2-aminoalcohol, 1,2-diol, imidazolium carbene, 4-(dimethylamino)pyridine, 2-(aminomethyl)pyridine, 4,7-diphenyl-1,10-phenanthroline, 4,7-dimethyl-1,10-phenanthroline, 5-methyl-1,10-phenanthroline, 5-chloro-1,10-phenanthroline, and 5-nitro-1,10phenanthroline; base represents a Bronsted base.