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With 1,1,3,3-Tetramethyldisiloxane; vanadium(V) oxytriisopropoxide; In toluene; at 60℃; for 20h;
General procedure: 40-Methyl-2-biphenylcarbonitrile 1d (Table 2 entry 4). To a nitrogen purged screw-capedvial containing 1d (630 mg, 3.3 mmol, 1.0 equiv) in 500 lL of toluene wereadded TMDS (5.8 mL, 32.8 mmol, 10.0 equiv) and V(O)(OiPr)3 (780 lL,3.3 mmol, 1.0 equiv) at rt. The mixture was then heated at 60 C for 20 h(the colorless solution turned into deep purple) and then cooled to roomtemperature. The clear solution was diluted with toluene (10 mL) and acidifiedusing aqueous H3PO4 85% (2.0 g diluted in 5.0 ml of water, 5.2 equiv). Theorganic layer was separated, washed with aqueous 1 m HCl (3 10 mL), driedover MgSO4 and concentrated under vacuum (40-methyl-2-biphenylcarboxaldehyde 2d was present in 70% estimated GC yield). Flashcolumn chromatography on silica gel (cyclohexane/ethyl acetate 9:1) afforded2d in 60% isolated yield
With copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In nitromethane; water; at 20 - 100℃; for 10h;
To a nitromethane (0.1 mL) solution of <strong>[1885-38-7]cinnamonitrile</strong> (1p) (30 mg, 0.232 mmol) were added H2O(1.0 mL), DBU (71 mg, 0.465 mmol), copper (I) iodide (8.8 mg, 0.0465 mmol), cesium (I) carbonate(38 mg, 0.116 mmol) at room temperature. The reaction mixture was heated at 100 C for 10 h andthen poured into water (50 mL). The organic layer was separated and the aqueous layer was extractedwith AcOEt. The combined organic layer was dried over MgSO4. The solvent was removed underreduced pressure. The residue was purified by preparative TLC on silica gel eluting with AcOEt-nhexane(1:1) to give (E)-4-phenylbut-3-enamide (2p)S1 (27 mg, 72%) as pale yellow powders.mp 142-144 C,
(b) (2E)-3-Phenyl-2-propenimidamide; Cinnanionitrile (25.0 g, 194 mmol) was dissolved in EtOH. The solution was cooled to 0 0C and HCl gas bubbled through the solution for 30 minutes. The solution was stirred at ambient temperature for 1 h and then concentrated under vacuum. The residue was dissolved in EtOH (100 niL), cooled to 00C and a solution of NH3/Me0H (7M, 69 mL, 484 mmol) was added dropwise through an addition funnel. Once added, the solution was allowed to warm to ambient temperature and stirred overnight and the resulting NH4Cl was filtered off. The solution was concentrated under vacuum and the resulting product was used without further purification (28.6 g crude). LC-MS: m/z 147.4 (MH+).
Step 2CinnamimidamideA solution of (2E)-3-phenylprop-2-enenitrile (25 g) in anhydrous ethanol (200 mL) was cooled to 0 C and hydrogen chloride gas bubbled through the solution for 30 minutes. The solution was stirred at ambient temperature for 16 hours and then concentrated under vacuum. The residue was dissolved in ethanol (100 mL), cooled to 0 C and a solution of ammonia/methanol (7 M, 69 mL) was added dropwise through an addition funnel. Once added, the solution was allowed to warm to ambient temperature and the resulting ammonium chloride was filtered off. The solution was concentrated under vacuum and the residue was dissolved in water, washed with ethyl acetate. The aqueous layer was dried to give the title compound (20 g), which was used next step without further purification. MS m/z: 147 (MH+).
(b) (2E)-3-Phenyl-2-propenimidamide; Cinnamonitrile (25.Og, 194mmol) was dissolved in EtOH (ethanol)(20OmL). The solution was cooled to 00C and HCI gas bubbled through the solution for 30 minutes. The solution was stirred at ambient temperature for 16h and then concentrated under vacuum. The residue was dissolved in EtOH (10OmL), cooled to 00C and a solution of NH3/MeOH (7M, 69mL, 484mmol) was added dropwise through an addition funnel. Once added, the solution was allowed to warm to ambient temperature and the resulting NH4CI was filtered off. The solution was concentrated under vacuum and the resulting white solid was used without further purification (26g crude). LCMS: m/z 147.4 (MH+).
(b) (2E)-3-Phenyl-2-propenimidamide; <n="106"/>Cinnamonitrile (25.Og, 194mmol) was dissolved in EtOH (ethanol) (20OmL). The solution was cooled to O0C and HCl gas bubbled through the solution for 30 minutes. The solution was stirred at ambient temperature for 16h and then concentrated under vacuum. The residue was dissolved in EtOH (10OmL), cooled to O0C and a solution of NHs/MeOH (7M, 69mL, 484mmol) was added dropwise through an addition funnel. Once added, the solution was allowed to warm to ambient temperature and the resulting NH4Cl was filtered off. The solution was concentrated under vacuum and the resulting white solid was used without further purification (26g crude). LCMS: m/z 147.4 (MH+).
With triethylamine; In neat (no solvent); at 20℃; for 1.08333h;Green chemistry;
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).
77%
With magnesia; (S)-1-benzyl-3-((S)-1-hydroxy-3-phenylpropan-2-yl)-5-isobutyl-4,5-dihydro-1H-imidazol-3-ium chloride; potassium tert-butylate; tetrabutylammomium bromide; palladium dichloride; In N,N-dimethyl-formamide; at 60℃; for 9h;
General procedure: To the mixture of imidazolium salt1 (0.4 % mmol) and PdCl2 (0.4 % mmol) in DMF (1mL) was added KOt-Bu (1.5 mmol), MgO (6mg), aryle halide (1mmol) and alpha, beta unsaturated (3mmol) and allowed to react at 60 C. After completion of the reaction, the mixture was allowed to cool toroom temperature andthen was extracted with CH2Cl2(10 mL). The organic layer was dried over MgSO4. The solvent was removed under reduced pressure and the crude material was purified bycolumn chromatography using hexane/EtOAc (30:3) as an eluent to give the product.
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