| 96% |
With potassium carbonate In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere; |
|
| 96% |
With potassium carbonate In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere; |
General procedure for N-arylation of N-H heterocycles witharyl halides
General procedure: In an oven dried 100 mL round bottom flask, Cu-grafted catalyst(0.05 g), aryl halide (1 mmol), N-H heterocycles (1.2 mmol), K2CO3(2 mmol), and 10 mL DMSO were stirred under nitrogen atmo-sphere, at 100C. The reaction mixtures were collected at differenttime interval and identified by GC-MS and quantified by GC anal-ysis. |
| 96% |
With potassium carbonate In lithium hydroxide monohydrate; dimethyl sulfoxide at 110℃; for 24h; |
|
| 95% |
With copper (I) iodide; 3-acetyl-2H-1-benzopyran-2-one; Cs2CO3 In N,N-dimethyl-formamide at 25℃; for 24h; Inert atmosphere; |
|
| 93% |
With potassium carbonate In dimethyl sulfoxide at 120℃; for 10h; Inert atmosphere; |
|
| 92% |
With potassium hydroxide In lithium hydroxide monohydrate at 120℃; for 12h; Inert atmosphere; |
|
| 92% |
With copper (I) iodide; potassium hydroxide In dimethyl sulfoxide at 80℃; for 20h; Inert atmosphere; |
|
| 90% |
With Cs2CO3 In N,N-dimethyl-formamide at 120℃; for 24h; Sealed tube; |
|
| 86% |
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.5h; |
General procedure for the catalytic N-arylationof imidazole
General procedure: The reaction flask, containing 0.02 g Cu(II) nanocatalyst(contains 0.4 mol% of Cu(II)), imidazole (2.0 mmol),K2CO3 (1.0 mmol), and corresponding aryl halide(1.0 mmol) in 2.5 cm3 DMF, was immersed in a preheated oil bath and the reaction mixture was stirred under air atmosphere at 120 C until no further conversion of the starting aryl halide was observed by thin-layer chromatography(TLC). After completion of the reaction, the resulting mixture was allowed to cool to room temperature,and then the catalyst was separated out by an external permanent magnet, washed with ethyl acetate (EtOAc) anddried. The residue mixture was diluted by H2O and extracted with EtOAc (3 9 10 cm3). The extracted organic phases were dried over anhydrous Na2SO4, filtrated, concentrated and, finally, purified by silica gel chromatography using petroleum ether/ethyl acetate to afford the corresponding pure N-arylimidazole. |
| 84% |
With oxalic acid hydrazide; potassium phosphate tribasic trihydrate; tetrabutylammonium bromide; 2,5-hexanedione; copper(II) oxide In lithium hydroxide monohydrate at 25 - 140℃; for 0.1h; Microwave irradiation; |
|
| 81% |
With pyridine; [Cu2(pda)3(ReO4)2]2*2H2O; Cs2CO3 at 170℃; for 3h; Inert atmosphere; |
|
| 81% |
With tripotassium phosphate tribasic; copper (I) iodide; tetrabutylammonium bromide In lithium hydroxide monohydrate at 120℃; for 8h; Green chemistry; |
2.4 General protocol for C-N coupling reaction
General procedure: A 10 mL of vial was charged with CuI (10 mg, 0.05 mmol), PSP (0.25 mmol, size less than 90 μM), TBAB (40 mg, 0.25 mmol), base (1.0 mmol), aryl halides (0.5 mmol), arylamine (2.0 mmol), H2O (1.0 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into an oil bath, which was preheated to 70 °C (90 °C for alkyl amine, 120 °C for imidazole). The reaction mixture was stirred for another 16 h (8 h for imidazole). After allowing the mixture to cool to room temperature, the reaction mixture was filtrated, the precipitates were washed with water and ethyl acetate thoroughly. The filtrate was extracted with ethyl acetate (3×25 mL). The combined organic phases was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel to afford the desired products. |
| 78% |
With copper oxide (I); Cs2CO3 In N,N-dimethyl-formamide at 120℃; for 12h; |
General procedure for the synthesis of N-arylated products 3a-3t
General procedure: A 10-mL vial was charged with aryl halide (0.5 mmol), Cs2CO3 (1 mmol), Cu2O (0.05 mmol), N-containing heterocycles (0.75 mmol), DMF (1 mL), and a magnetic stir bar. The mixture was stirred at 120 °C (130 °C for entry 19). The reaction mixture was held at this temperature for 12 h (24 h for entry 18, 20, 21, and 25). After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether as the eluent) to provide the target products 3a-3t. |
| 77% |
With copper oxide (I); 2,6-bis(2-methylhydrazine-1-carbonyl)pyridine 1-oxide; tetrabutylammonium bromide; sodium hydroxide In lithium hydroxide monohydrate at 130℃; for 24h; Schlenk technique; |
3.1.2 General Procedure fortheSynthesis of 3a-3w
General procedure: A 25mL Schlenk tube was charged with Cu2O(0.05mmol),ArX (0.5mmol), NHR1R2(0.75mmol), NaOH (1mmol),TBAB (0.1mmol), L1 (0.1mmol) and water (1mL). Themixture was stirred at 130°C for 24h. The reaction mixturewas extracted with ethyl acetate (3 × 10mL), washed withwater and brine, dried over anhydrous Na2SO4,and concentratedin vacuo. The residue was purified by flash columnchromatograph on silica gel (ethyl acetate/petroleum etheras the eluent) to provide the target products 3a-3w. |
| 74% |
With Cs2CO3 In dimethyl sulfoxide at 110℃; for 24h; Green chemistry; |
|
| 73% |
With bis(8-hydroxyquinolato)copper(II); Cs2CO3 In dimethyl sulfoxide at 100℃; for 12h; |
|
| 70% |
With (2-furyl)methyl alcohol; tripotassium phosphate tribasic; copper (I) iodide In lithium hydroxide monohydrate at 150℃; for 21h; Sealed tube; Green chemistry; |
|
| 68% |
With copper oxide (I); 1-(2-methylhydrazine-1-carbonyl)isoquinoline 2-oxide; tetrabutylammonium bromide; sodium hydroxide In ethanol; lithium hydroxide monohydrate at 120℃; for 12h; Schlenk technique; |
4.2. General procedure for the synthesis of 3a-3w and 6
General procedure: A 25 mL Schlenk tube was charged with Cu2O (0.05 mmol), ArX (0.5 mmol), NHR1R2 (0.75 mmol), NaOH (1 mmol), TBAB (0.1 mmol), L2 (0.1 mmol) and H2O/EtOH (1 mL, 1/1, v/v). The mixture was stirred at 120 °C for 12 h. The reaction mixture was extracted with ethyl acetate (3 10 mL), washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel(ethyl acetate/petroleum ether as the eluent) to provide the target products 3a-3w and 6. |
| 68% |
With copper(II) oxide; sodium hydroxide; L-ascorbic acid In propane-1,2,3-triol at 120℃; for 12h; |
|
| 68% |
With propane-1,2,3-triol; copper(II) oxide; sodium hydroxide; L-ascorbic acid at 120℃; for 12h; |
|
| 65% |
With potassium carbonate In lithium hydroxide monohydrate at 100℃; for 24h; High pressure; |
General procedure for the Ullmann reaction catalyzed by Cu/HCS-MA-F127
General procedure: To a stirred solution of H2O (4 mL), aryl halide (1.0 mmol), nucleophile(1.2 mmol), Cu/HCS-MA-F127 and K2CO3 (2 mmol) wereadded at room temperature. Next, the reaction mixture was heated to100 °C in air and stirred for 24 h. After cooling down to room temperature,the catalyst Cu(at)HCS-MA-F127 was separated by centrifugation.The reaction mixture was partitioned by adding ethyl acetate (20mL) and water (20 mL). Subsequently, the organic phase was separatedand the aqueous phase was extracted with ethyl acetate (20 mL) twice.The combined organic phases were washed with brine, dried overNa2SO4, and concentrated in vacuo. Finally, the crude product waspurified by column chromatography with silica gel, eluting with apetroleum ether/ethyl acetate solvent mixture, to give the pure product. |
| 64% |
With copper (I) iodide; N-tetradecyl lactosamine; Cs2CO3 In lithium hydroxide monohydrate at 100℃; for 12h; |
|
| 60% |
With 2-(2-tert-butylhydrazinecarbonyl)pyridine-1-oxide; tetrabutylammonium bromide; copper atom; potassium hydroxide In lithium hydroxide monohydrate at 120℃; for 12h; Sealed tube; Green chemistry; |
Typical experimental procedure
Cu (0.05 mmol), L4 (0.1 mmol), aryl halides(0.5 mmol), imidazoles (0.75 mmol), KOH (1 mmol), TBAB (0.15 mol), and H2O(1 mL) were added to a 10 mL sealed tube. The reaction mixture was reacted at120 C in a pre-heated oil bath for 12 h. The reaction mixture was cooled to room temperature, diluted with 10 mL H2O, and then the mixture was extracted with ethyl acetate (3 20 mL). The combined organic phases were washed withwater and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel (ethyl acetate/petroleum ether, 2:1 to pure ethyl acetate) to afford the target products. |
| 59% |
With C26H18CuN2O8S2(2-)*2Na(1+); tetrabutylammonium bromide; sodium hydroxide In lithium hydroxide monohydrate at 100℃; Sealed tube; |
|
| 42% |
With norfloxacin; copper(II) bromide; sodium hydroxide In dimethyl sulfoxide at 120℃; for 24h; |
|
| 40% |
With copper (I) iodide; N,N′-di-β-D-glucopyranosylethylenediamine; Cs2CO3 In lithium hydroxide monohydrate at 100℃; for 24h; |
General procedure of CuI/L5 catalyzed Ullmann-type C-N coupling of aryl halides andnitrogen nucleophiles in water
General procedure: To a stirred solution of H2O (5 ml) were added CuI (0.1 mmol, 19 mg), aryl halides (1.0 mmol),nitrogen nucleophiles (1.2 mmol), Cs2CO3 (2 mmol, 651 mg) and L5 (0.1 mmol) were added tothe solution, subsequently the mixture was heated to 100 °C under air and stirred for 24 h. Whenthe reaction was finished, the mixture was cooled and partitioned by adding the ethyl acetate (20ml) and water (20 ml). Then, the organic phase was separated and the aqueous phase wasextracted with ethyl acetate (20 ml) twice. The combined organic phases were washed withsaturated brine, dried over Na2SO4, and concentrated in vacuo. Then the crude product waspurified by column chromatography through silica gel, eluting with ethyl acetate/petroleum ethersolvent mixture, to give the pure product. |
| 20% |
With copper chloride (I); sodium hydroxide; 3-(diphenylphosphanyl)propanoic acid In dimethyl sulfoxide at 100℃; for 12h; Sealed tube; |
Procedure for N-arylation of imidazoles:
General procedure: CuCl (0.04mmol), L2 (0.08mmol), aryl idione or bromide (0.5mmol), imidazole or 1H-benzo[d]imidazole (0.75mmol), NaOH (1mmol), and DMSO (1mL) was added to a 5mL tube, then sealed. The mixture was stirred at 100°C for certain time. After cooling to room temperature, the mixture was quenched with 10mL H2O and extracted with EtOAc (3×20mL). The combined EtOAc extracts were dried with anhydrous Na2SO4 and filtrated and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE/EtOAc (from 2:1 (v/v) to pure EtOAc) as the eluent to afford the desired products. |
| 99 % Spectr. |
With Cs2CO3 In dimethyl sulfoxide at 100℃; for 24h; |
|
| 86 %Spectr. |
With (1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-imidazol-2-yl)copper(I) chloride; Cs2CO3 In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; |
|
|
With tripotassium phosphate tribasic; N,N-dimethyl acetamide; Cu(isonicotinate)2 In n-hexadecane at 100℃; for 6h; |
|
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