| 98% |
With copper(II) acetate monohydrate; caesium carbonate; In N,N-dimethyl-formamide; at 110℃; for 24h;Inert atmosphere; |
General procedure: To a solution of Cu(OAc)2·H2O (0.01 mmol) in DMF (2 mL) were added aryl iodide (1.2 mmol), nitrogen-containing heterocycle (1.0 mmol), and Cs2CO3 (2 mmol) under nitrogen atmosphere. The mixture was stirred at 110 C for 24 h. After cooling to ambient temperature, the mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel. |
| 97% |
With copper phthalocyanine; sodium hydroxide; In dimethyl sulfoxide; at 100℃; |
General procedure: In a 50mL RB, N-H heterocycles (1.0mmol), aryl halide (1mmol), Cu(II)Pc (0.01mmol), NaOH (1.5mmol) and DMSO (2mL) was added. This reaction mixture was stirred to a preheated oil bath at 100C for 8-12h. After completion of the reaction, it was cooled to room temperature and 20mL ethyl acetate was added. It was filtered; solid catalyst was separated and washed with 2×5mL ethyl acetate. The washing and filtrate were combined and washed with water. Ethyl acetate was removed under reduced pressure and product was purified with column chromatography. |
| 91% |
With caesium carbonate;iron(III) acetylacetonate; copper(II) oxide; In N,N-dimethyl-formamide; at 90℃; for 30h;sealed tube;Conversion of starting material; |
Following General Procedure A (90 0C, 30 hours), 1H-pyrrole (104 muL, 1.5 mmol) is coupled with iodo-benzene (112 muL, LO mmol). The crude brown oil is purified by flash chromatography on silica gel (eluent: hexanes) to provide 130 mg (91 % isolated yield) of the desired product as a white solid. IdentificationMp: 600C. 1H NMR (400 MHz, CDCI3): delta 7.28-7.34 (m, 4H, H2^e), 7.14-7.15 (t, 1 H,H4), 6.99-7.00 (t, 2H, H7lio), 6.26-6.27 (t, 2H, H8,9).13C NMR (100 MHz, CDCI3): delta 140.82 (C1), 129.60 (C3>5), 125.66 (C4),120.57 (C216), 119.37 (C7)10), 110.46 (C8,9).IR (KBr): v (cnY1) = 3142, 3102, 2924, 1603, 1556, 1511, 1459, 1400, 1326, 1255, 1189, 1083, 1014, 919, 895, 758, 719, 608, 509. <n="52"/>GC/MS: rt = 14.09 min, M/Z = 143.HRMS: 143.0740 (M). Theoretical: 143.0735. |
| 90% |
With copper(I) oxide; caesium carbonate; N-phenyl-2-pyridincarboxamide-1-oxide; In dimethyl sulfoxide; at 120℃; for 20h;Inert atmosphere; |
General procedure: In 50 mL round bottom flask, aryl halide (1.0 mmol), pyrazole (1.2 mmol), ligand (0.04 mmol), Cu2O (0.10 mmol), cesium carbonate (2.0 mmol), and dry solvent (20 mL) were placed under nitrogen atmosphere. The reaction mixture was heated in oil bath up to specified temperature under constant stirring for 20 h and then allowed to cool to room temperature. The reaction mixture was filtered through a plug of Celite in a fritted filter funnel and washed with ethyl acetate. If DMSO is used as solvent, it is extracted by washing the filtrate with 25 mL water for three times. The organic phase was dried over anhydrous MgSO4 and was removed under reduced pressure to provide the crude product which was purified by column chromatography on silica gel, using hexane and ethyl acetate in 3:1 ratio, respectively, as an eluent. |
| 86% |
With toluene-4-sulfonic acid; at 165℃; for 0.916667h;Ionic liquid; Microwave irradiation; |
General procedure: In a new sealed pressure regulation 10-mL pressurized vial were placed aryl halide (1 mmol), p-toluenesulfonic acid (1 mmol, 0.172 g), [DBU][HOAc] (1.5 mL), N-nucleophile (2 mmol), and a Teflon-coated magnetic stir bar. The vessel was closed with a snap-on cap, stirred at room temperature for 5 min and then placed into the MW cavity. Microwave irradiation of 100 W at a set temperature of 165C was used and the reaction mixture was held under these conditions for the specified time. After completion of the reaction (monitored through TLC), the mixture was cooled to room temperature and was poured to a vessel containing distilled water. This was extracted with ethyl acetate (3*10 mL) and the combined organic phase was washed with brine (2*10 mL), dried over Na2SO4, and was concentrated under rotary vacuum evaporator. The crude product was purified by column chromatography using a mixture of ethyl acetate/n-hexane as eluent. |
| 86% |
With caesium carbonate; at 135℃; for 4h; |
General procedure: A mixture of pyrrole (3 ml), Cs2CO3 (1.96 g, 6 mmol), Cu0/4A or Cu2+/4A (0.3 g) and the appropriate aryl halide (3 mmol) were stirred at 135 C (bath temperature) for 4-36 h. Before adding to the mixture, Cu2+/4A was preheated at ca. 150 C for 1 h. The mixture was filtered, the solid was washed with dichloromethane. The filtrate was extracted with deionised water (2 x 40 ml). The organic phase was dried over Na2SO4 and concentrated in vacuum. The residue was distilled and clarified. Certain products (3c, 3f) were purified by recrystallization from MeOH. |
| 86% |
With potassium carbonate; In toluene; at 110℃; for 10h;Catalytic behavior; |
To a solution of N-H heterocycle (1 mmol) and aryl halide (2 mmol) in toluene were added catalyst (0.07 g, 0.016 mmol) and K2CO3 (276 g, 2 mmol) and the mixture stirred at 110 C for the specified time. The progress of the reaction was monitored by TLC. The reaction mixture allowed cooling to room temperature and ethyl acetate (25 mL) was added and the mixture stirred for 15 min to ensure product removal from catalyst. Then the catalyst was filtered, washed with ethyl acetate (2 9 25 mL). The organic layer was evaporated under vacuum on a rotary evaporator and the crude product was obtained. Further purification was achieved by column chromatography using ethyl acetate/n-hexane gradient. Structural assignments of the products are based on their 1H NMR and melting point. |
| 85% |
With 2-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethan-1-ol; copper(II) acetate monohydrate; sodium t-butanolate; In N,N-dimethyl-formamide; at 120℃; for 0.5h; |
General procedure: A mixture of N-unsubstituted compound 2 (1.0 mmol), aryl halide 1 (1.2 mmol), and t-BuONa (1.2 mmol) was stirred in DMF (0.3 mL) inthe presence of Cu(OAc)2·H2O (1 mol%) and 2-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanol (1 mol%) at 120 C for the time given inTable 2. The mixture was washed with EtOAc; after removal of thesolvent, the residue was purified by column chromatography (silicagel, petroleum ether-EtOAc). |
| 85% |
With potassium hydroxide; In dimethyl sulfoxide; at 100℃; for 5h; |
General procedure: A mixture of aryl iodide (1.0 mmol), Het-NH (1.2 mmol), KOH (2 mmol), nanomagnetic Fe3O4-TiO2/Cu2O (0.010 g equal to 1.4 mol% Cu2O) and anhydrous DMSO (2 mL) was stirred at 100 C. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and diluted by ethyl acetate and the catalyst was separated by an external magnet from the mixture, washed with acetone, dried in an oven at 80 C for 3 h and re-used for a consecutive run under the same reaction conditions. The combined ethyl acetate layer was washed with water and dried over anhydrous MgSO4. The residue was purified by recrystallization or short column chromatography on silica gel to afford the target products in excellent yield. |
| 85% |
With copper(l) iodide; N-hydroxyphthalimide; sodium methylate; In dimethyl sulfoxide; at 90℃; for 12h; |
In a 25 mL round bottom flask, add 3 mmol of sodium methoxide, 3 mL of DMSO solution,Then add 10 mol% of CuI (0.2 mmol, 38 mg) and 10 mol% ofN-hydroxyphthalimide (L1, 0.2 mmol, 33 mg), and stirred at room temperature for 30 minutes.Then, iodobenzene dissolved in DMSO (2 mL) was added dropwise to the reaction solution.(2mmol, 408mg) and pyrrole (2mmol, 134mg), the addition was completed within 3 minutes.The temperature of the oil bath was raised to 90 C. and the reaction was stirred for 12 h. After the reaction, 10 mL of saturated saline was added.Extract with ethyl acetate (3 × 10 mL), combine the extracts,The crude product after removing the solvent by rotary distillation was purified and separated by column chromatography to obtain a white solid.0.243 g, yield 85%. |
| 83% |
With potassium hydroxide; In dimethyl sulfoxide; at 100℃; for 4h; |
General procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), Cu2O/nano-CuFe2O4 magnetic composite (0.010 g) and anhydrous DMSO (2 mL) was stirred at 100 C. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and with diluted ethyl acetate and the catalyst was separated by an external magnet from the mixture, washed with acetone, dried in an oven at 80 C for 3 h and re-used for a consecutive run under the same reaction conditions. The combined ethyl acetate layer was washed with water, dried over anhydrous MgSO4, The residue was purified by recrystallization or short column chromatography on silica gel to afford the target products in excellent yield. |
| 80% |
With tetrabutylammomium bromide; copper; lithium hydroxide; In water; at 120℃; for 24h; |
General procedure: General procedure: iodobenzene (1.0mmol), pyrazole (1.5 mmol), LiOH (2.0 mmol), TBAB(0.2 mmol), active Cu (0.1 mmol) and 2 mL H2O were added to a 10 mL flask. The mixture was heated in an oil bath at 120?. When the reaction completed, the resulting mixture was cooled to room temperature and the product was extracted by ethyl acetate (10 mL×3). The combine dextracts were washed by brine (15 mL) , dried over MgSO4 and evaporated under reduced pressure. Further purification by silica gel column chromatography (5:1 petroleum ether/ethylacetate) give 1-phenyl-1H-pyrazole (2a, 0.126 g, 88%) as a Colorless liquid. |
| 75% |
With copper(ll) sulfate pentahydrate; sodium hydroxide; In dimethyl sulfoxide; at 110℃; for 12h;Sealed tube; |
General procedure: CuSO4·5H2O (12.50 mg, 0.05 mmol), the aryl iodide or bromide(1.0 mmol), pyrrole (1.5 mmol), NaOH (80 mg, 2 mmol), and DMSO(2 mL) were placed in a 10 mL sealed tube. The mixture was heatedat 110 C in a preheated oil bath for 12 h. It was then cooled to roomtemperature, diluted with 20 mL H2O, and the mixture was extractedwith ethyl acetate (3 × 20 mL). The combined organic phases waswashed with water and brine, dried over anhydrous Na2SO4, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel (ethyl acetate/petroleum ether, 1 : 100)to afford the target products. All C-N coupling products reported hereare known products and were characterised by GC-MS and 1H NMR,which were compared with the previously reported dates. |
| 62% |
With copper(l) iodide; tetrabutylammomium bromide; triethylentetramine; In water; at 125℃; for 12h; |
General procedure: Iodobenzene (1.0 mmol), imidazole (1.5 mmol), TEPA (2.0 mmol), TBAB (0.3 mmol), CuI (0.1 mmol), and 3 mL H2O were added to a 10 mL flask, which was subsequently capped with a rubber balloon. The mixture was stirred in a preheated oil bath at 125 C for 12 h. After cooling the mixture to the room temperature, 5 mL water was added and the product was extracted by ethyl acetate (10 mL×3). The combined organic layer was washed by brine (15 mL), dried over anhydrous MgSO4, and evaporated under the reduced pressure. Further purification by silica gel column chromatography (6:1 petroleum ether/ethyl acetate) give the 1-phenyl-1H-imidazole. |
| 57% |
With copper(l) iodide; manganese(II) fluoride; (1R,2R)-1,2-diaminocyclohexane; potassium hydroxide; In water; at 100℃; for 24h; |
General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999% purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98% purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis. |
| 52% |
With copper(l) iodide; potassium carbonate; dimethyl sulfoxide; glycerol; at 120℃; for 24h; |
General procedure: To a 25 ml two-necked round-bottom flask was placed a mixture of aryl iodide (1 mmol), indole (1.5 mmol), CuI (0.1 mmol), K2CO3 (2 mmol), and DMSO (1 mmol) in 2 ml glycerol. The reaction mixture was heated in an oil bath at 120C for 24 h with continuous stirring. After completion of reaction monitored by TLC, the reaction mixture was cooled to room temperature and was extracted with diethyl ether three times (3×10 ml). The combined organic layers were washed with brine solution and dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (60-120 mesh) to provide the N-aryl indole in 88% yield. The remaining glycerol/copper catalytic mixture was reused for further recycling study by adding fresh DMSO (1 mmol) to the catalytic system. All the products are well known in the literature and were confirmed by comparison of their spectroscopic data with literature data. |
| 52% |
With copper(l) iodide; potassium carbonate; dimethyl sulfoxide; In ethylene glycol; at 120℃; for 24h;Green chemistry; |
General procedure: To a 25ml two-necked round-bottom flask was placed a mixture of aryl iodide (1mmol), indole (1.5mmol), CuI (0.1mmol), K2CO3 (2mmol), and DMSO (1mmol) in 2ml glycerol. The reaction mixture was heated in an oil bath at 120C for 24h with continuous stirring. After completion of reaction monitored by TLC, the reaction mixture was cooled to room temperature and was extracted with diethyl ether three times (3×10ml). The combined organic layers were washed with brine solution and dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (60-120 mesh) to provide the N-aryl indole in 88% yield. The remaining glycerol/copper catalytic mixture was reused for further recycling study by adding fresh DMSO (1mmol) to the catalytic system. All the products are well known in the literature and were confirmed by comparison of their spectroscopic data with literature data. |
| 48% |
With copper(I) oxide; potassium phosphate; tetrabutylammomium bromide; In water; at 130℃; for 24h;Closed system; |
General procedure for N-arylation of amines:The N-nucleophile (1.47 mmol), Cu2O (Sigma-Aldrich, 99.99% purity, 0.147 mmol), K3PO4 (2.94 mmol), the aryl halide (1.76 mmol), phase transfer catalyst (0.147 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 130 C for 24 h, then the heterogeneous mixture was cooled to RT and diluted with dichloromethane. The resulting solution was directly filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of all products was confirmed by 1H and 13C NMR spectroscopic analysis. |
| 85%Chromat. |
With C16H12ClN3OPdS; potassium hydroxide; In dimethyl sulfoxide; at 110℃; for 10h; |
General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 M%) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy. |
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
