| 99% |
With [P5(η3-allyl)(4,4'-(CF3(CF2)9CH2OCH2)-2,2'-bpy)][OTf]; triethylamine In N,N-dimethyl-formamide at 145℃; for 2h; Microwave irradiation; |
|
| 98% |
With tris(triphenylphosphine) cobalt(I) chloride; potassium carbonate In various solvent(s) at 100℃; for 24h; |
|
| 98% |
With tetradecyl(trihexyl)phosphonium chloride; anhydrous Sodium acetate In lithium hydroxide monohydrate at 50℃; for 2h; |
|
| 98% |
With tetra-n-butylammonium acetate; triethylamine In butan-1-ol at 80℃; for 24h; Inert atmosphere; |
|
| 98% |
With triethylamine In N,N-dimethyl-formamide at 130℃; for 1h; |
|
| 96% |
With triethylamine In N,N-dimethyl-formamide at 100℃; for 3h; Green chemistry; |
General experimental procedures for Heck reaction
General procedure: The reactions were conducted in similar way as for Sonogashira reaction. Stirring the mixture of aryl halide (1.00 mmol), styrene derivative (1.50 mmol), Pd(at)MOF-808 (3 mol %), Et3N (2.00 mmol) and DMF (5.00 mL) at 100 °C for 2-8 h. After cooling down the mixture to room temperature, evaporating the solution under reduced pressure. After that, purifying the residue by silica gel column chromatography to collect the target coupling products |
| 95% |
With tripotassium phosphate tribasic In N,N-dimethyl-formamide at 140℃; for 2h; |
4.5 General procedure for Mizoroki-Heck coupling reactions
General procedure: In a 10-mL round-bottomed flask, a mixture of aryl iodide (1mmol), methyl acrylate (1.2mmol), and base (1.2mmol), was placed in 4ml of DMF, then a solution of complex 3a (0.05% mol) in 1mL of DMF was added. The reaction mixture was refluxed for the time stated in Tables1 and 2 at 140°C. The reaction mixture was poured into water (20mL) and extracted with ether or hexane (2×30mL). The combined organic layers were dried over anhydrous sodium sulfate. After the removal of the solvent in vacuo, the resulting crude was purified by column chromatography on silica gel (hexane-ethyl acetate) to give (E)-methyl p-methyl cinnamate (The purified product was identified by means of determination of mp and by 1H and 13C NMR, the data obtained are consistent with literature) [33]. |
| 95% |
With triethylamine at 100℃; for 0.5h; Ionic liquid; Green chemistry; |
Typical Procedure for the Mizoroki-Heck Reaction.
General procedure: In a typical procedure, iodobenzene (1.0 mmol, 0.203 g), methyl acrylate (1.2 mmol, 0.108 mL), potassium carbonate (1.5 mmol, 0.207 g), ZrO2ECP-Pd nanocatalyst (0.31 mol%, 0.005 g), and [bmim]PF6 (1 g, 3.5 mmol) were allowed to reac tat 100 °C. Upon the completion of the reaction which was monitored by TLC, the reaction mixture was cooled to room temperature and the catalyst was separated by centrifuge. n-Hexane (5 mL) was added to the reaction mixture and extraction was done for 15 min with vigorous stirring.(55)The organicl ayer was combined and concentrated under reduced pressure to give the crude product. The final product was purified by thin layer chromatography using n-hexane/ethyl acetate (50/1) to afford the pure product. |
| 95% |
With triethylamine In N,N-dimethyl-formamide at 100℃; for 17h; Inert atmosphere; Schlenk technique; |
2.5.1 Using Dimethyl Formamide (DMF) as the Solvent
General procedure: A Schlenk reactor kept under N2(g) atmosphere was filled with the aryl iodide (0.2mmol or 1eq.), the olefn (0.4mmolor 2eq.), triethylamine (Et3N, 83 μL, 0.6mmol or 3eq.),CSPPh2-Pd sufficient for 0.5mol% of Pd, and degassed DMF (1mL). The reaction system magnetically stirred at 100°C for 17h. Next, the reaction was removed from heatingand allowed to cool down to room temperature. Then, 5mL of ethyl acetate was added, and the crude mixture was washed with distilled water (3 × 5mL). The organic phasewas dried with magnesium sulfate, filtered, and concentrated for column chromatography (ethyl acetate/hexanes) for the isolation of the target product, which was identified by 1H and 13C NMR. |
| 94% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; |
|
| 93% |
With palladium diacetate; Potassium bicarbonate at 140℃; for 0.15h; Microwave irradiation; neat (no solvent); stereoselective reaction; |
|
| 93% |
With triethylamine In acetonitrile at 82℃; for 3h; diastereoselective reaction; |
General procedure for Heck and Sonogashira coupling reactions
General procedure: Aryl halide (1 mmol), alkene or alkyne (1.2 mmol), triethylamine (3 mmol) and 25 mg (0.07 mol%) Pd0-Mont. were added to 10 ml acetonitrile solution and the reaction mixture was stirred at 82 ◦C for stipulated time period. The progress of the reactions was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and the solid catalyst was separated from the mixture by filtered through sintered funnel (G-3). The recovered catalyst was washed with acetone, dried in a desiccator and stored for another consecutive reaction run. The product was extracted with ethyl acetate followed by evaporation of the solvent to yield the crude product which was finally purified by silica gel column chromatography using ethyl acetate and hexane as eluents. The products were identified by 1H NMR, mass spectrometry and melting point determination followed by their comparison with the standard literature data [45]. |
| 93% |
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere; |
|
| 92% |
With bis(acetonitrile)palladium(II) chloride; tripotassium phosphate tribasic; N,N'-(1,2-ethanediylidene)bishexahydro-1H-azepin-1-amine In N,N-dimethyl-formamide at 80℃; for 6h; |
|
| 92% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; |
|
| 92% |
With bis(acetonitrile)palladium(II) chloride; C9H13N3S; triethylamine In N,N-dimethyl-formamide at 160℃; for 0.05h; Microwave irradiation; regioselective reaction; |
|
| 92% |
With Pd immobilized on pine needle-derived active carbon; diethylaminomethyl-polystyrene at 130℃; for 4h; |
|
| 91% |
With triethylamine In N,N-dimethyl acetamide at 120℃; for 2h; |
|
| 91% |
With triethylamine In lithium hydroxide monohydrate; N,N-dimethyl-formamide; toluene at 100℃; for 20h; |
|
| 91% |
With triethylamine In neat (no solvent) at 120℃; for 0.833333h; Sealed tube; Inert atmosphere; Green chemistry; |
1.7 Typical procedure for the solvent-free Heckreaction
General procedure: aryl halide (1.0 mmol), olefin (1.5 mmol), triethylamine (1.5 mmol), Pd/Fe3O4PIL-NH2(0.011 mol% based on aryl halide) were introduced into a 5-mLscrew-capped tube after it was purged with argon for 10 min. The mixture wasstirred at 120 C for a giventime and then cooled to room temperature, 5 mL ethyl acetate/ethanol (1:1 v/v)was added into the tube. The catalyst Pd/Fe3O4PIL-NH2 was separated byan external magnet and washed with ethyl acetate/ethanol (1:1 v/v) (3×3 mL).Then the combined organic phase was concentrated, and the residue was purifiedby column chromatography over silica gel to afford the corresponding product. Theproducts were analyzed by NMR spectroscopy. |
| 91% |
With triethylamine In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 130℃; for 3h; |
2.3. General procedure for synthesis of trans-alkenes
General procedure: In a typical method, 1 mmol of bromobenzene, 1 mmol of methylacrylate, 0.04 g of PdNPsPANI/silica-HNS, and 2 mmol of Et3N wereadded to 5 mL of DMF:H2O (1:1) and allowed to stirrer at 130 C. Thereaction completion was monitored by TLC (n-hexane and ethyl acetatemixture as solvent-5:1). After completion of the reaction, the reactionwas cooled to room temperature, the catalyst was removed by filtration.The catalyst was then washed with Et2O (3 5 mL). The organic layerwas separated and dried over anhydrous Na2SO4. The solvent wasevaporated under reduced pressure to give the corresponding arylolefins.To optimize the reaction conditions, GC was used to investigatethe yields under each condition. The NMR spectroscopic data of known compounds were found to be identical with those reported in the literature. |
| 91% |
With triethylamine In neat (no solvent) at 120℃; for 1.33333h; Inert atmosphere; |
|
| 90% |
With triethylamine In acetonitrile at 100℃; for 23h; |
|
| 90% |
With triethylamine In N,N-dimethyl-formamide at 120℃; for 3h; |
General procedure for the Heck coupling reaction
General procedure: Aryl halide (1 mmol), alkene (1.5 mmol), triethylamine (2 mmol) and h-Fe3O4mTiO2-NH2-Pd (20 mg) were added to 3 mL DMF and the reaction mixture was stirred at 120Cfor the required time. After completion of the reaction, the reaction mixture was cooled toroom temperature and diluted with hot ethanol (10 ml). Then, the catalyst was separatedby an external magnet from the cooled mixture, washed with acetone, dried in an ovenand re-used for a consecutive run under the same reaction conditions. The filtrate wasconcentrated and the resulting residue was purified by short column chromatography onsilica gel to afford the desired product. |
| 90% |
With tripotassium phosphate tribasic; palladium diacetate; 2-benzothiazolecarboxaldehyde N,N-diphenylhydrazone In N,N-dimethyl acetamide for 1h; Irradiation; |
|
| 90% |
With potassium carbonate In neat (no solvent) at 40℃; for 2h; Irradiation; |
|
| 87% |
With Sodium hydrogenocarbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 22h; |
|
| 87% |
With tetrabutylammonium bromide; C19H24Br2N4OPd; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Sealed tube; |
|
| 86% |
With Cs2CO3 In lithium hydroxide monohydrate at 100℃; for 0.916667h; Green chemistry; |
|
| 85% |
With (3aS,7aS)-1,3-di-o-tolyl-octahydro-benzoimidazole-2-thione; triethylamine In N,N-dimethyl-formamide at 80℃; for 5h; |
|
| 85% |
With anhydrous sodium carbonate; 1,3-bis(2,4,6-trimethylphenyl)imidazolinium chloride In N,N-dimethyl-formamide at 150℃; for 20h; |
|
| 85% |
With C44H56N6O4Pd2(4+)*4Cl(1-); potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Sealed tube; Inert atmosphere; |
General Procedure for Heck Reaction
General procedure: Aryl halide (5 mmol), olefin (10 mmol), K2CO3 (5 mmol), and 1 (0.1 mol%)were taken in DMF (10mL) in a sealed tube (25mL) fitted with a Teflon cap underN2 atmosphere and the mixture was heated with stirring at 80 C for 4 h and cooledto room temperature. The solvent was evaporated under reduced pressure on arotary evaporator. The residue was extracted using EtOAc (310 mL) and driedover Na2SO4, and the solvent was removed on a rotary evaporator. The crude residueobtained was purified by column chromatography on silica gel, 60-120 mesh(petroleum ether-EtOAc, 98:2) |
| 85% |
With tripotassium phosphate tribasic In lithium hydroxide monohydrate at 80℃; for 0.916667h; |
|
| 85% |
With triethylamine In neat (no solvent) at 20℃; for 0.333333h; Green chemistry; diastereoselective reaction; |
Typical Procedure for the Mizoroki-Heck Cross-Coupling Reaction
General procedure: FMMWCNTs(at)CPA(at)SMTU(at)PdII NPs (IV) (0.35 mol-%,0.015 g) were added to a mixture of triethylamine (NEt3) (2 mmol, 0.202 g), methyl acrylate (1.2 mmol, 0.108 mL), and iodobenzene (1.0 mmol, 0.203 g) in solvent-free conditions at room temperature. After the completion of the reaction (15 min)which was monitored by TLC, the nanocatalyst was separated by a magnetic field, washed with ethyl acetate, and dried at room temperature for 24 h to be used in the next run. The reaction mixture was then extracted with ethyl acetate (55 mL) and the combined organic layer was dried over anhydrous Na2SO4. After evaporation of the solvent, the crude product was purifiedby TLC (or column chromatography using n-hexane/ethylacetate (50 : 1)) using n-hexane/ethyl acetate (8 : 2) to produce the pure methyl cinnamate (0.153 g, 98% yield). |
| 84% |
With 3,4,5,6-tetrahydro-2H-pyran-2-one at 130℃; for 2h; Green chemistry; |
|
| 84% |
With triethylamine In N,N-dimethyl acetamide at 130℃; for 5h; |
|
| 79% |
With 4-(pyridin-2-yl)pyrimidin-2-aminepaladium(II) chloride; anhydrous Sodium acetate In ethylene glycol at 120℃; for 6h; Green chemistry; |
|
| 77% |
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 11h; |
|
| 77% |
With tributyl-amine; tetrabutylammonium bromide; anhydrous sodium carbonate at 150℃; for 0.025h; microwave irradiation; |
|
| 77% |
With triethylamine In N,N-dimethyl-formamide at 100℃; for 8h; Green chemistry; |
General procedure for Heckreaction:
To a round bottom flask containing 3 mol% of Pd-PCS, mix-ture of organic halide (1 equiv.), olefinic compound (1 equiv.) andtriethyl amine (1 equiv.) were added. DMF was used as the solvent.A water cooled condenser was placed on the flask and stirred forabout 8 h at 100C. The reaction mixture was cooled, filtered andwashed initially with dichloromethane and then with water. Thefiltrate was extracted with diethyl ether. The ether layer was col-lected and dried over anhydrous sodium sulphate. It was filteredand solvents were removed in a rotary vacuum evaporator. Theresidue was recrystallized from dichloromethane. |
| 76% |
With potassium carbonate In N,N-dimethyl-formamide for 2h; Heating; |
|
| 76% |
With tetrabutylammonium bromide; anhydrous Sodium acetate In N,N-dimethyl-formamide at 140℃; for 30h; |
|
| 55% |
With tetrabutylammonium hydrogensulfate; potassium carbonate In lithium hydroxide monohydrate for 0.133333h; microwave irradiation; |
|
| 54% |
With triethylamine In carbon dioxide at 80℃; for 60h; |
|
| 30% |
With triethylamine In N,N-dimethyl-formamide at 140℃; for 3h; Sealed tube; Inert atmosphere; Green chemistry; |
2.2. General procedure for Heck reaction
General procedure: To a dried sealed tube, aryl halide (0.25 mmol), activated alkene(0.3 mmol), Na2CO3 (0.75 mmol), polymer supported palladium catalyst(2 mol%) were added followed by the addition of DMF (2 ml). Thereaction mixture was then stirred at 120 °C under N2 atmosphere andprogress of the reaction was monitored by TLC. After completion of thereaction (3 h), the reaction mixture was extracted with ethyl acetateand water. The organic layer was separated and dried over anhydrousNa2CO3 and concentrated on rotary evaporator. The obtained crudeproduct was separated by column chromatography using appropriateEthylacetate/Hexanemixture (85 to 95: 15 to 5) and the yields werenoted. The structure of the products was characterized using spectroscopic analyses and in comparison with literature data. |
|
With tributyl-amine at 100℃; for 8h; |
|
|
With triethylamine In N,N-dimethyl-formamide Heating; |
|
| 100 % Spectr. |
With triethylamine In acetonitrile at 100℃; for 12h; |
|
|
With triethylamine In N,N-dimethyl acetamide at 205℃; microwave irradiation; |
|
| 94 % Chromat. |
With triethylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 7h; |
|
| 90 % Chromat. |
With triethylamine In N,N-dimethyl-formamide at 120℃; for 0.5h; microwave irradiation; |
|
| 95 %Chromat. |
With [PdMe(MeCN){G1-CH(3,5-Me2pz)2}][BAr(f)4]; triethylamine In acetonitrile at 80℃; for 23h; Inert atmosphere; |
|
| 97.8 %Chromat. |
With porous chitosan microspheres supported palladium catalyst In ethylene glycol; dimethyl sulfoxide at 110℃; for 5h; |
3.6. General procedure for Pd/PCMS catalyzed heck cross-coupling reactions in DMSO
General procedure: To a 20 ml round bottom flask containing 5.0 ml DMSO, added aromatic iodide (1.0 mmol), acrylate (2.0 mmol), Pd/PCMS (0.01 mmol) and potassium acetate (7.5 mmol). The resulting solution was allowed to stir and the reaction progress was monitored by TLC and/or GC/MS analysis. After completion, the reaction mixture was cooled down, and then quenched with 10 ml of water and extracted three times with ethyl acetate (3 × 20 ml). The combined organic layer was washed with water, saturated brine, and then dried over anhydrous Na2SO4. Solvent was removed under a reduced pressure. The cross-coupling product was purified by silica gel chromatography with petroleum ether and ethyl acetate. The cross-coupling products are known and they are all consistent with the chemical structures as characterized from 1H NMR and GC/MS analysis. |
|
With [PdI2{1-Mes-3-(2-phtCH2CH2)Imz-2-ylidene}(γ-picoline)]; triethylamine In N,N-dimethyl-formamide at 65℃; for 3h; Inert atmosphere; Schlenk technique; |
|
|
With C120H111N2O14*Pd(2+)*2Br(1-); triethylamine In N,N-dimethyl-formamide at 120 - 160℃; for 24h; |
|
|
With triethylamine In N,N-dimethyl-formamide at 120℃; for 4h; |
|
|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; |
|
|
With naphthalene; C218H190Br2N4O28Pd; triethylamine In N,N-dimethyl-formamide at 130℃; Inert atmosphere; |
|
|
With triethylamine In N,N-dimethyl-formamide at 120℃; for 3h; regioselective reaction; |
|
|
With triethylamine In N,N-dimethyl-formamide at 120℃; for 3h; regioselective reaction; |
|
|
With potassium carbonate In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 120℃; for 12h; |
|
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