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CAS No. : | 14592-56-4 | MDL No. : | MFCD00013122 |
Formula : | C4H6Cl2N2Pd | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RBYGDVHOECIAFC-UHFFFAOYSA-L |
M.W : | 259.43 | Pubchem ID : | 6093782 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 34.66 |
TPSA : | 47.58 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.77 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.57 |
Log Po/w (WLOGP) : | 2.44 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | -0.19 |
Consensus Log Po/w : | 0.83 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.44 |
Solubility : | 0.947 mg/ml ; 0.00365 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.18 |
Solubility : | 1.72 mg/ml ; 0.00661 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.1 |
Solubility : | 204.0 mg/ml ; 0.785 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.07 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P261-P270-P271-P264-P280-P361+P364-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 | UN#: | 3439 |
Hazard Statements: | H301+H311+H331 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 29% 2: 19% 3: 8% | In chloroform-d1 react. of starting compds. in CDCl3 at 50°C is monitored by (1)H-NMR spectroscopy.; unreacted initial org. material (44%) is remained after 5 days. NMR identification of resulting compds.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With d(4)-methanol In chloroform-d1 byproducts: HCl, Pd(OH)Cl; addn. of CD3OD to CDCl3 soln. of starting compds. and monitoring of react. by (1)H-NMR spectroscopy.; formation of org. compd. after 95 h.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In dichloromethane N2 or Ar atmosphere; stirring (3 h); partial evapn., addn. of EtOH, filtration, drying; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | In dichloromethane Ar-atmosphere; stirring at room temp. for 40 min; filtration, concn. (vac.), recrystn. (CH2Cl2); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In dichloromethane; benzene byproducts: MeCN; equimolar mixt. of ligand and Pd complex dissolved in warm CH2Cl2; evapd.; stirred with benzene under reflux for 30 min; filtered; solid recrystd. from CH2Cl2-ether (twice); dried under vac.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In dichloromethane under N2; soln. of PdCl2(CH3CN)2 in CH2Cl2 treated with soln. of the pyrazole in CH2Cl2, stirred at room temp. for 12 h; concd., ppt. filtered off, washed with Et2O and dried in vacuo; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile under N2atm. soln. (PdCl2(MeCN)2) in MeCN was treated with soln. ligand in MeCN and stirred for 14 h; soln. was concd., ppt. was filtered, washed with MeCN and dried in vacuo; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; acetonitrile byproducts: CH3CN; soln. of 6-aza-2-thiothymine in CH3OH added dropwise to suspn. of Pd-complex in CH3OH/CH3CN; mixt. stirred at room temp.; soln. filtered; filtrate kept at 25°C; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With CH3CN In dichloromethane; acetonitrile addn. of AgClO4 soln. to Pd-complex (both in CH3CN, pptn., stirring for 15 min), filtration, addn. of 2 equiv. of ligand soln. (in CH2Cl2, stirring for 1 h); evapn. to dryness, extn. (CH3CN), filtration, volume. reduction, crystn.(acetone addn. if necessary); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In not given (N2); organic ligand added to Pd-complex; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In benzene stirring overnight; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In dichloromethane soln. of Pd-complex in CH2Cl2 was treated with soln. of ligand in CH2Cl2for 12 h in Schlenk apparatus; concd., filtered, washed with Et2O, dried in vacuo; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In benzene dissolving, concn. (vac.); dissolving in CH2Cl2, crystn. on ether vapour action (5 d); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In dichloromethane under N2; a soln. of a ligand (3.96 mmol) in CH2Cl2 was added to a soln.of Pd-contg. compd. (3.6 mmol) in CH2Cl2; stirring for 0.5 h; the soln. was concd. to small vol. and dild. with diethyl ether to ppt.;crystn. from hot acetonitrile; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol soln. of N-based ligand and sodium fumarate in MeOH added to soln. of Pdcomplex in MeOH; filtered off; washed (H2O, MeOH); dried (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol soln. of N-based ligand and sodium fumarate in MeOH added to soln. of Pdcomplex in MeOH; filtered off; washed (H2O, MeOH); dried (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol soln. of N-based ligand and sodium fumarate in MeOH added to soln. of Pdcomplex in MeOH; filtered off; washed (H2O, MeOH); dried (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In dichloromethane (N2); using Schlenk techniques; dissolving of PhOP(OC10H6)2 (2 equiv.) and PdCl2(MeCN)2 (1 equiv.) in CH2Cl2; stirring at room temp. for 2 h; concn. on rotary evaporator; addn. of hexane; pptn., centrifugation; drying under vac., elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In dichloromethane (Ar, Schlenk technique); stirring CH2Cl2 soln. of 1:1 mixt. of palladiumcompd. and ferrocene deriv. for 1 h; concg., addn. of hexanes, keeping cold for 20 h, filtration, washing with diethyl ether, drying, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In 1,2-dichloro-ethane for 16h; Inert atmosphere; | Pd(quinox)Cl2:Quinoline-2-oxazoline (695.6 mg, 3.51 mmol) was weighed into an oven dried 100 mL round bottomed flask. A magnetic stir bar was added and the reaction was placed under N2 atmosphere. DCE (30 mL) was added to the reaction flask and stirred until quinox was completely dissolved. Pd(CH3CN)2Cl2 (880.3 mg, 3.39 mmol) was added to the reaction flask. The reaction mixture was allowed to stir for 16 h to form quinoline-2-oxazoline according to the reaction A precipitate formed and was filtered off using a Buchner funnel. The Pd(quinox)Cl2 complex was isolated (1.24 g, 99% yield) as an orange powder. Pd(quinox)Cl2 is completely insoluble in all common NMR solvents and the reaction becomes homogeneous upon treatment with aqueous TBHP. A decomposition temperature of 285° C. was measured |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane complex PdCl2(CH3CN)2 reacted with 2-(2-dicyclohexylphosphinophenyl)-1-methyl-benzoimidazole in CH2Cl2 for 1 h at room temp. under N2; XRD; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In toluene; at 20℃; for 12h; | I.2 Synthesis of Isonitrile-Pd ComplexesGeneral Procedure:[Pd(CH3CN)2Cl2] was dissolved in toluene and two equivalents of the isonitrile was added. The mixture was stirred 12 h at room temperature. The precipitate was filtered off, washed with cold pentane and dried under reduced pressure to afford the title compounds.Example IIIcis-[PdCl2(2,6-dimethylphenyl isonitrile)2][Pd(CH3CN)2Cl2] (200 mg, 780 μmol) was dissolved in toluene (8 ml) and 2,6-dimethylphenyl isonitrile from example II (212 mg, 1.60 mmol) was added. The mixture was stirred 12 h at ambient temperature. The precipitate was filtered off, washed with cold pentane (3×10 ml) and dried under reduced pressure to yield the title compound as white solid (333 mg, 757 μmol, 97%).IR (KBr): ν=2363, 2208, 1632, 1473, 1384, 1170, 771, 717, 576, 499, 453; HRMS (FAB+) C18H18N2ClPd [M-Cl-]+: calc. 403.0193. found: 403.0138. |
97% | In toluene; at 20℃; for 12h; | I.2 Synthesis of Isonitrile-Pd ComplexesGeneral Procedure:[Pd(CH3CN)2Cl2] was dissolved in toluene and two equivalents of the isonitrile was added. The mixture was stirred 12 h at room temperature. The precipitate was filtered off, washed with cold pentane and dried under reduced pressure to afford the title compounds.Example IIIcis-[PdCl2(2,6-dimethylphenyl isonitrile)2][Pd(CH3CN)2Cl2] (200 mg, 780 μmol) was dissolved in toluene (8 ml) and 2,6-dimethylphenyl isonitrile from example II (212 mg, 1.60 mmol) was added. The mixture was stirred 12 h at ambient temperature. The precipitate was filtered off, washed with cold pentane (3×10 ml) and dried under reduced pressure to yield the title compound as white solid (333 mg, 757 μmol, 97%).IR (KBr): ν=2363, 2208, 1632, 1473, 1384, 1170, 771, 717, 576, 499, 453; HRMS (FAB+) C18H18N2ClPd [M-Cl-]+: calc. 403.0193. found: 403.0138. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.73 g | Stage #1: dichloro bis(acetonitrile) palladium(II); triphenylphosphine In acetone at 20℃; for 18h; Inert atmosphere; Stage #2: lithium bromide In acetone for 3.5h; Inert atmosphere; Stage #3: lithium bromide In acetone for 504h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol; dichloromethane at 20℃; for 24h; Reflux; | trans-[PdCl2(PI)2] (1) 1-phenylimidazole (0.288 g, 2 mmol) was added slowly to a solution of [PdCl2(CH3CN)2] (0.259 g, 1 mmol) in 30 mL CH3OH:CH2Cl2 (50:50 V/V) mixture at room temperature. The resulting mixture was refluxed with stirring at room temperature for 24 h, during this the color of the solution changed from light yellow to dark yellow. The resulting solution was filtered and left at room temperature for slow evaporation crystallization. After three days, yellow color crystals were separated, washed with diethyl ether and dried. Yield: (0.325 g, 70%). Anal. Calc. for C18H16Cl2N4Pd: C, 46.45; H, 3.44; N, 12.04. Found: C, 46.66; H, 3.56; N, 12.34. IR(cm-1, Nujol):ν = 3422, 3142(C-H), 3011, 2923, 2853, 2359, 2341, 1636(C=N), 1597, 1513, 1457, 1384, 1306, 1277, 1233, 1159, 1129(C-N), 1095, 1062, 1000, 966, 819, 766, 738(C-H), 692, 668, 653, 610, 530. Far-IR:ν (Pd-Cl) = 353 cm-1. 1H NMR (δ ppm, 400 MHz, CDCl3, 298 K): 8.40(s, 2H, Imd), 7.60(d, 2H, J = 1.3 Hz, Imd), 7.37-7.53(m, 10H, J = 6.7 Hz, Ph), 7.15(t, 2H, J = 2.0 Hz, Imd). 13C{1H} NMR (CDCl3): 137.60(C-Imd), 135.90(C-Ph), 129.10(C-Ph), 128.60(C-Ph), 125.60(C-Imd), 122.30(C-Imd). UV-Vis: λmax (DMSO, ε[dm3 mol-1 cm-1]) = 342 (10976), 260 (8404). FAB-MS m/z 465(464), [M]+; 429(430), [M]+-Cl; 393(391), [M]+-Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In methanol; dichloromethane at 20℃; for 24h; Reflux; | trans-[PdCl2(MPI)2] (2) 1-(4-methoxyphenyl)-1H-imidazole (0.348 g, 2 mmol) was added slowly to a solution of [PdCl2(CH3CN)2] (0.259 g, 1 mmol) in 30 mL CH3OH:CH2Cl2 (50:50 V/V) mixture at room temperature. The resulting mixture was refluxed with stirring at room temperature for 24 h, during this the color of the solution changed from light yellow to dark yellow. The resulting solution was filtered and left at room temperature for slow evaporation crystallization. After 2 weeks, yellow color powder was separated, washed with diethyl ether and dried. Yield: (0.383 g, 73%). Anal. Calc. for C20H20Cl2N4O2Pd: C, 45.71; H, 3.81; N, 10.67. Found: C, 45.80; H, 3.96; N, 10.80. IR(cm-1, Nujol):ν = 3424, 3129, 3092, 2933, 2834, 1609(C=N), 1564, 1519, 1440, 1413, 1381, 1361, 1337, 1307, 1251, 1184, 1133(C-N), 1099, 1067, 1027, 955, 831, 810, 797, 730, 690, 666, 615, 524. Far-IR: ν (Pd-Cl) = 354 cm-1. 1H NMR (δ ppm, 400 MHz, CDCl3, 298 K): 7.65-7.74(m, 6H, J = 6.5 Hz, Imd), 7.39-7.44(m, 8H, J = 7.5 Hz, Ph), 3.49(s, 6H, OCH3). 13C{1H} NMR (CDCl3): 158.80(C-Ph), 136.10(C-Imd), 129.30(C-Ph), 124.80(C-Imd), 123.10(C-Imd), 122.60(C-Ph), 114.20(C-Ph) 54.60(C-OCH3). UV-Vis: λmax (DMSO, ε[dm3 mol-1 cm-1]) = 343 (10630), 260 (8449). FAB-MS m/z 525(524), [M]+; 489(491), [M]+-Cl; 453(451), [M]+ -Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In toluene at 30℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | at 35℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With triethylamine; In dimethyl sulfoxide; at 60 - 80℃; for 9h; | A mixture of 3a (0.514 g, 0.969 mmol), PdCl2(NCCH3)2 (0.246 g, 0.948 mmol), and NEt3 (0.251 g, 2.48 mmol) in DMSO (4 mL) was stirred at 60 C for 2h and then at 80 C for 7h. The resulting precipitates were filtered, washed with acetone, and dried under vacuum (0.269 g, 0.647 mmol, 68%). Anal. Calcd for C14H14Cl2N4Pd: C, 40.46; H, 3.40; N, 13.48. Found: C, 40.33; H, 3.31; N, 13.30. 1H NMR (400MHz, addition of LiCl, DMSO-d6): δ=4.01 (s, 3H, Me), 6.34 (d, 1H, -CH2-, 13Hz), 6.54 (d, 1H, -CH2-, 13Hz), 7.43 (m, 2H, H4 or H5, and H4″), 7.51 (dd, 2H, H3″), 7.69-7.76 (m, 4H, H4 or H5, H2″, H4′ or H5′), 7.86 (s, 1H, H4′ or H5′). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With Benzimidazol-2-thiol; In ethanol; at 85℃; for 48h;Inert atmosphere; | A suspension of PdCl2 (177 mg, 1 mmol) in dryacetonitrile (2 mL) and dry benzene (10 mL) was deoxygenatedand stirred at 85 8C under argon for 3 h to formmonomeric <strong>[14592-56-4]PdCl2(MeCN)2</strong>. The solvent was evaporated todryness and the residue was charged under argon with (L,202 mg, 0.5 mmol) in absolute ethanol (10 mL) and stirredat 85 8C for 48 h. The reaction mixture was cooled to roomtemperature and allowed to stand to form a linden-greensolid product, which was filtered, washed with ether, anddried under vacuum (284 mg, 75%). Dec. over 260 8C. Molarconductivity: 72.8 V1cm2mol1, 1:1 electrolyte. Found(calculated), C21H17Cl2N5PdS2; C, 42.98 (43.42); H, 3.10(2.95); N, 11.89 (12.06); S, 10.92 (11.04). FT-IR: see Table 1.1H NMR (DMSO-d6), dH ppm: 5.23 (d, J = 14.0, 4H, CH2), 7.33(td, J1 = 7.8, J2 = 1.2 Hz, 2H), 7.40 (td, J1 = 7.8, J2 = 1.3 Hz, 2H),7.45 (d, J = 8.0 Hz, 2H), 7.84 (d, J = 8.0 Hz, 2H), 8.15 (t,J = 7.8 Hz, H), 8.51 (d, J = 7.8 Hz, 2H), 14.19 (s, 2H, NH). 13CNMR (DMSO-d6), dC ppm: 35.35 (CH2), 111.47, 119.47,122.99, 124.03, 125.49, 133.17, 140.63, 143.40, 149.01,157.34 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: Bis(triazolium) diiodide 5 (200 g, 0.27 mmol) was treated with Ag2O (74 mg, 0.32 mmol) in CH2Cl2 and the mixture was stirred for 24 h under N2 atmosphere in the dark. An aliquot of the reaction mixture was evaporated and 1H NMR and ESI mass spectra were recorded to check the complete conversion of the iodide salt to the corresponding Ag complex 6. The absence of the triazolium proton resonance at 8.97 ppm in the 1H NMR spectrum clearly indicated the complete conversion of 5 to silver complex 7. After 24 h stirring [PdCl2(CH3CN)2] (75.8 mg, 0.29 mmol) was added to the reaction mixture and stirring was continued for another 24 h. The reaction mixture was filtered through a sintered crucible and solvent was evaporated under vacuum to give complex 8 as a pale yellow solid. It was washed with diethyl ether and ethyl acetate several times to obtained pure product (8) in 96% yield (171 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In methanol; benzene at 50℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In dichloromethane at 40℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethylamine In tetrahydrofuran at 20 - 30℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triethylamine In tetrahydrofuran at 20 - 30℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With triethylamine; In methanol; dichloromethane; at 20℃; for 3h; | [PdCl2(CH3CN)2] (26mg, 0.1mmol) was added to a solution of H2L (44mg, 0.1mmol) in 5mL of a CH2Cl2/MeOH (v/v 1/1) mixture, and then three drops of Et3N were added. The mixture was stirred for 3h at room temperature to obtain a clear yellow solution. Slow evaporation of the solvents gave light yellow crystals of 2. The product was filtered off, washed with MeOH and dried in vacuum. Yield 65% (35mg). Elemental analysis: Anal. Calc. for C22H26N6S2Pd: C, 48.48; H, 4.81; N, 15.42; S, 11.77. Found: C, 48.21; H, 4.85; N, 15.35; S, 11.60%. IR (KBr, cm-1): 3434 (m), 3052 (w), 2967 (m), 1547 (vs), 1503 (vs), 1467 (s), 1420 (s), 1379 (s), 1223 (m), 1089 (m), 749 (m), 618 (m). 1H NMR (500MHz, CDCl3, ppm): 1.33 (t, J=7.0Hz, 3H, CH3), 1.36 (t, J=7.0Hz, 3H, CH3), 2.78 (s, 3H, N=C-CH3), 3.03 (d, J=5.0, 3H, NCH3), 3.65 (m, 1H, NCH2), 3.74 (m, 1H, NCH2), 4.04 (m, 1H, NCH2), 4.24 (m, 1H, NCH2), 4.95 (s, br, NH), 6.53 (d, J=8.0Hz, 1H, C6H4), 6.83 (t, J=7.7Hz, 1H, C6H4), 6.86 (t, J=7.6Hz, 1H, C6H4), 7.15 (t, J=7.5Hz, 2H, Ph), 7.21 (t, J=7.2Hz, 1H, Ph), 7.37 (d, J=7.4Hz, 2H, Ph), 7.59 (d, J=8.0Hz, 1H, C6H4). +ESI MS (m/z): 544.98, 100%, [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In dichloromethane at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate In N,N-dimethyl acetamide; water at 70℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox; | 3.3. Synthesis and characterization of 5a and 5b Into a 20 mL brown Schlenk tube were placed Pd(PPh3)4(0.05 mmol, 0.0578 g), PdCl2(MeCN)2 (0.05 mmol, 0.0130 g), norbornene(2.1 mmol, 0.2 g), and K2CO3 (2.0 mmol, 0.277 g). Then, 4-iodotoluene (2.0 mmol, 0.26 mL) as well as 8 mL DMA (containing 0.5 M H2O) were transferred to the tube by syringe under N2. The mixturewas stirred at 70 C for 20 h. The solutionwas washed withH2O and ether. The organic layer was extracted twice with ether. It was then purified by Centrifugal Thin Layer Chromatography (CTLC)using CH2Cl2 as eluent. The solvent was removed under reduced pressure. The yield of 5a is 98% (0.0848 g, 0.0980 mmol). The residue was subjected to crystallization process by CH2Cl2 and hexanesand yellow crystals were resulted. Similar processes were taken forthe preparation of 5b except that dicyclopentadiene (2.0 mmol,0.264 g) was used. The yield of 5b is 98% (0.0922 g, 0.0980 mmol). Yellow crystals were resulted in crystallization process by CH2Cl2and heptane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate In N,N-dimethyl acetamide; water at 70℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox; | 3.3. Synthesis and characterization of 5a and 5b General procedure: Into a 20 mL brown Schlenk tube were placed Pd(PPh3)4(0.05 mmol, 0.0578 g), PdCl2(MeCN)2 (0.05 mmol, 0.0130 g), norbornene(2.1 mmol, 0.2 g), and K2CO3 (2.0 mmol, 0.277 g). Then, 4-iodotoluene (2.0 mmol, 0.26 mL) as well as 8 mL DMA (containing 0.5 M H2O) were transferred to the tube by syringe under N2. The mixturewas stirred at 70 C for 20 h. The solutionwas washed withH2O and ether. The organic layer was extracted twice with ether. It was then purified by Centrifugal Thin Layer Chromatography (CTLC)using CH2Cl2 as eluent. The solvent was removed under reduced pressure. The yield of 5a is 98% (0.0848 g, 0.0980 mmol). The residue was subjected to crystallization process by CH2Cl2 and hexanesand yellow crystals were resulted. Similar processes were taken forthe preparation of 5b except that dicyclopentadiene (2.0 mmol,0.264 g) was used. The yield of 5b is 98% (0.0922 g, 0.0980 mmol). Yellow crystals were resulted in crystallization process by CH2Cl2and heptane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In benzene at 80℃; for 24h; Schlenk technique; Inert atmosphere; | |
In benzene at 110℃; for 48h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: 2,6-bis(3-tert-butylimidazolium-1-yl)pyridine dichloride With silver(l) oxide In methanol; dichloromethane at 20℃; for 6h; Stage #2: dichloro bis(acetonitrile) palladium(II) In dichloromethane for 12h; Stage #3: sodium tetrafluoroborate In methanol; water | 4.6 Preparation of [Pd(CNC)Cl]BF4 (4) A mixture of 2,6-bis(3-tert-butylimidazolium-1-yl)pyridine dichloride (80.4mg, 0.203mmol) and Ag2O (48.3mg, 0.208mmol) in MeOH/CH2Cl2 (v/v, 1/9) (10mL) was stirred at room temperature for 6h. After filtration and evaporation to dryness, the residue was dissolved in CH2Cl2 (10mL), followed by addition of [PdCl2(NCMe)2] (52.3mg, 0.202mmol). After stirring for 12h, the mixture was filtrated and removed the solvent. To a MeOH (2mL) solution of the crude product was added NaBF4 (110mg, 1.00mmol) in H2O (10mL). After concentration of the mixture, the resulting precipitate was filtrated, washed with a small amount of H2O, and dried to give [Pd(CNC)Cl]BF4 (4) as a yellow solid (69.6mg, 62%). IR (KBr, pellet): ν(BF) 1083 (s)cm-1. 1H NMR (CD3CN): δ 8.35 (t, J=8.3Hz, 1H, 4-py), 7.86 (d, J=2.4Hz, 2H, imid), 7.72 (d, J=8.2Hz, 2H, 3,5-py), 7.53 (d, J=2.4Hz, 2H, imid), 1.87 (s, 18H, tBu). 13C{1H} NMR (CD3CN): δ 166.4 (CNHC), 151.7 (2,6-py), 147.1 (4-py), 123.0 (imid), 117.1 (imid), 109.6 (3,5-py), 62.6 (CMe3), 31.2 (CMe3). ESI-MS (m/z): 466.2 [M-BF4]+. Elemental analysis (%) calcd for C19H25N5PdClBF4: C, 41.33; H, 4.56; N, 12.68; found: C, 41.20; H, 4.11; N, 12.70. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane for 24h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In toluene;Inert atmosphere; | A suspension of [PdCl2(NCMe)2] (0.453 g, 1.175 mmol) in toluene(20 mL) was mixed with <strong>[4027-54-7]5-phenyl-3-(trifluoromethyl)-1H-pyrazole</strong> (0.50 g, 2.35 mmol). Yield: 0.83 g (79 %). dH (400MHz, DMSO-d6): 6.34 (1H, s, 4-H pz), 7.44 (3H, t, J7.6 Hz, 3’-H,4’-H and 5’-H), 7.91 (2H, d, J 7.6 Hz, 2’-H, 6’-H), 13.75 (1H, s, N-Hpz); dC (100 MHz, DMSO-d6):101.5 (C-4 pz), 123.5 (q, 1JF,C = 38.2Hz, C-F3), 125.9 (C-3’, C-5’), 129.4 (C-4’), 129.6 (C-2’, C-6’); 128.5(C-1’), 144.6 (C-3 pz), 150.1 (C-5 pz). dF (DMSO-d6): -60.41 (CF3). IR(Diamond ATR, cm-1): n(N-H) = 3226 cm-1; n(C=N) = 1611 cm-1.HR-MS (ESI): m/z (%)=600.9453 (100) [M+H]+. Found: C, 39.90,H, 2.35; N, 9.31 %. Calc. for C20H14Cl2F6N4Pd: C, 39.92; H, 2.35; N,9.31 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In chloroform for 1h; | Dichlorido(imidazolidine-2-thione)(triphenylphosphine)palladium(II)MeOH (1*MeOH): Complex 1*MeOH was preparedby adding a mixture of imidazolidine-2-thione (imzt) (40 mg; 0.39 mmol) and triphenylphosphine (101 mg;0.39 mmol) in CHCl3/CH3OH (1:1, 4 mL) to an orange solution of [PdCl2(CH3CN)2] (100 mg; 0.39 mmol) in CH3OH (10 mL). After stirring the mixture for 1 h, the resulting suspension was filtered and the yellow solid was washed with methanol, chloroform and pentane and dried under vacuum. Yield: 77%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In acetonitrile;Heating; | HL2 (0.08 g, 0.5 mmol) in acetonitrile (10 ml) was added to a hot solution of cis-PdCl2x(MeCN)2 (0.13 g, 0.5 mmol) in acetonitrile (10 ml). The resulting mixture was stirred, and the complex was precipitated and collected by filtration. The physical properties and analytical data of IIa are listedin Table 1, and the spectral data of IIa are listed in Table 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With triethylamine; In acetonitrile;Heating; | General procedure: cis-PdCl2x(MeCN)2 (0.26 g, 1 mmol) in hot acetonitrile (10 ml) was added to a solution of the respective ligand (2 mmol) and Et3N (0.29 ml, 2 mmol) in acetonitrile (10 ml). Precipitated yellow crystals were collected by filtration, washed with acetonitrile and dried in air. The physical properties and analytical data of compounds I-III are listed in Table 1, and the spectral data of compounds I-III are listed in Table 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.24 g | With sodium hydroxide In acetonitrile for 12h; | Preparation of complex 1 (Pd2L4) The synthetic method for preparation of compound 1 is asfollows: 0.09 g PdCl2 (0.5 mmol) and CH3CN (50 mL) wereplaced in a 100-mL round-bottomed flask equipped with areflux condenser and a magnetic stirrer. The mixture wasstirred and warmed to 70 °C to give a light orange solution.Then, 0.25 g ligand (1 mmol) and sodium hydroxide 0.5 M(2 mL) were added. The reaction mixture refluxed for 12 hand the green solid appeared. The green solution filtered andwashed with CH3CN (3 × 10 mL). The product was recrystallizedwith DMF and was used without further purification(yield 0.24 g, 80.0%, m.p. 207 °C). IR (KBr, cm-1): 3100w,2920w, 1593s, 1454s, 1317s, 1149s, 1087s, 989m, 831m,773m, 680m, 578m. 1H-NMR (DMSO-d6, ppm): 2.48 (-CH3),7.2-7.6 (benzene ring), 6.48, 7.23, 7.87 and 8.21 (pyridinering). Elemental analysis Calcd (%) for 1, C48H44N8O8Pd2S4:C, 47.96; H, 3.66; N, 9.32. Found: C, 47.62; H, 3.64; N, 9.27. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | 1,4-Diphenyl-3-methyl-1,2,3-triazolium iodide (1a) (2.18g, 6mmol) was treated with freshly prepared silver oxide (1.67g, 7.2mmol, 1.1 equiv.) in CH2Cl2 (35mL). The solution was stirred at room temperature in the dark for 16h under nitrogen atmosphere. The silver carbene complex thus generated was not isolated, it was directly treated with Pd(CH3CN)2Cl2 (1.71g, 6.6mmol, 1.1 equiv.) and stirred for 8h. The reaction mixture was passed through a bed of celite, and then removal of CH2Cl2 gave complex 2a as a pale yellow solid (1.19g) in 96% yield. mp: 189-191C; 1H NMR (500MHz, CDCl3) δ 8.37-8.35 (m, 4H), 7.97-7.95 (m, 4H), 7.58 (s, 12H), 4.06 (s, 6H); 13C NMR (125MHz, CDCl3) δ 143.9, 138.5, 130.7, 130.6, 129.6, 129.3, 125.3, 38.0; ESI-MS: HRMS: m/z calcd for C30H27N6Pd2Cl4 [M+H]+ 822.9121, found 822.9136. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In toluene Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1445 g | In tetrahydrofuran; at 20.0℃; for 9.5h;Inert atmosphere; | Take a dry 10L three-neck reaction flask, dry nitrogen is fully replaced and under nitrogen flow protection,Add 5.5 L of anhydrous tetrahydrofuran, stir and add 540 g of bis(acetonitrile)palladium dichloride.The obtained ligand di-tert-butyl-4-dimethylaminophenylphosphine was further reacted for 30 minutes, and a yellow solid was precipitated. After the reaction was continued for 9 hours at room temperature,After filtration, the filter cake was dipped in anhydrous tetrahydrofuran, drained and dried in a vacuum oven at 60 C.Obtaining a yellow crystalline powdery target product, namely dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium, yielding 1440 g to 1445 g,Elemental analysis showed that the product content exceeded 98.0%, the palladium content exceeded 15.0%, and the palladium calculated yield was 97.7% to 98.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In 1,2-dichloro-ethane at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With triethylamine; In acetonitrile; at 25℃; for 0.5h; | Triazene L1 (52.65 mg, 0.1927 mmol, 1.0 eq) was dissolved inCH3CN (5 mL), to this solution triethylamine (38.94 mg, 0.3854 mmol,2 eq) was added with stirring. To the resulting reaction mixture, a solutionof [Pd(CH3CN)2(Cl)2] (50 mg, 0.1927 mmol, 1.0 eq) in CH3CN(5 mL) was slowly added, and the resulting mixture was stirred for30 min at room temperature, during which time a red precipitateformed. The reaction mixture was filtered to obtain a reddish microcrystallinesolid, which was recrystallized by vapor diffusion of pentaneinto a concentrated solution of the product in CH2Cl2 at room temperatureto give red crystals, suitable for X-ray diffraction analysis(53.17 mg, 0.0703 mmol, 73%). MP=198-201 C. IR(KBr): 3014,2957, 1652, 1595, 1557, 1499, 1428, 1368, 1251, 1187, 1084, 826,748 cm-1. 1H NMR [CDCl3, 400 MHz]: δ 7.85 (dd, J=8.4, 1.6 Hz, 2H,ArA3), 7.54 (dd, J=8.4, 1.2 Hz, 2H, ArA6), 7.37 (dd, J=9.2, 5.2 Hz,4H, ArB2,6), 7.33 (td, J=7.2, 1.6 Hz, 2H, ArA5), 6.98 (t, J=8.8 Hz, 4H,ArB3,5), 6.93 (td, J=8.4, 1.2 Hz, 2H, ArA4), 3.62 (s, 6H, OCH3(A7)). 13C{1H} NMR [CDCl3, 100 MHz]: δ 169.8 (CA7), 161.1 (d, J=243.0 Hz,CB4), 151.8 (CA1), 146.9 (d, J=2.0 Hz, CB1), 134.3 (CA5), 131.9 (CA3),124.7 (d, J=8.0 Hz, CB2,6), 122.2 (CA4), 120.0 (CA6), 116.9 (CA2),114.7 (d, J=22.0 Hz, CB3,5), 53.8 (CA8). HRMS (ESI-TOF) m/z:[M+Na] Calc. for C28H22N6O4F2Pd2Na 780.9649; Found 780.9647.Anal. Calc. for C28H22N6O4F2Pd2 (757.36): C, 44.40; H, 2.93; N, 11.10.Found, C, 44.19; H, 2.85; N, 11.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With triethylamine; In acetonitrile; at 25℃; for 0.5h; | Complex 5 was prepared in the same manner as 4 using triazene L2(55.82 mg, 0.1927 mmol, 1.0 eq). Red crystals (49.34 mg, 0.0626 mmol,65%). MP=222-224 C. IR(KBr): 3023, 2937, 1651, 1557, 1476, 1433,1358, 1194, 1157, 1085, 819, 752 cm-1. 1H NMR [CDCl3, 400 MHz]: δ7.86 (dd, J=8.4, 1.6 Hz, 2H, ArA3), 7.53 (dd, J=8.4, 0.8 Hz, 2H,ArA6), 7.37 (d, J=8.8 Hz, 4H, ArB2,6), 7.35 (td, J=8.4, 1.6 Hz, 2H,ArA5), 7.23 (d, J=8.8 Hz, 4H, ArB3,5), 6.97 (td, J=8.0, 1.2 Hz, 2H,ArA4), 3.66 (s, 6H, OCH3(A8)). 13C {1H} NMR [CDCl3, 100 MHz]: δ 169.8(CA7), 151.6 (CA1), 149.3 (CB1), 134.3 (CA5), 131.9 (CA3), 131.1 (CB4),128.1 (CB3,5), 124.4 (CB2,6), 122.5 (CA4), 120.2 (CA6), 117.2 (CA2), 53.9(CA8). HRMS (ESI-TOF) m/z: [M+Na] Calc. for C28H22N6O4Cl2Pd2Na812.9046; Found 812.9042. Anal. Calc. for C28H22N6O4Cl2Pd2(790.26): C, 42.56; H, 2.81; N, 10.63. Found, C, 42.58; H, 2.78; N,10.52. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine; In tetrahydrofuran; at 20℃; for 3h;Glovebox; | To a THF solution (3 mL) of Pd(CH3CN)2Cl2 (0.104 g, 0.40 mmol)was dropwise added a solution of the chiral iminophenyl oxazolinylphenylamines (IPOPA) tridentate ligand (0.187 g, 0.40 mmol)and Et3N (0.044 g, 0.44 mmol, 1.1 eq.) in THF (2 mL) at room temperature in the glovebox. The mixture was stirred at room temperature for 3 h and then filtered. The filtrate was evaporated, and the solid residue was washed with toluene several times (3×5 mL). After removal of the combined organic filtrates in vacuo, the residue was recrystallized from toluene and hexane at -30 C to give the product as ared solid (170 mg, 70% yield). 1H NMR (400 MHz, CDCl3): δ 7.68 (d,1H), 7.37 (s, 1H), 7.33-7.15 (m, 7H), 7.10 (d, 1H), 6.90-6.75 (m, 2H),4.93-4.80 (m, 1H), 4.58-4.33 (m, 2H), 3,34-3.23 (m, 1H), 3,19-3.09(m, 1H), 2.60-2.46 (m, 1H), 1.50-1.25 (m, 12H), 0.97 (d, 3H), 0.91 (d,3H); 13C NMR (100 MHz, CDCl3): δ 161.5, 160.6, 150.2, 147.7, 142.3,140.4, 134.3, 133.8, 132.9, 130.0, 127.2, 126.0, 123.6, 123.2, 122.9,119.2, 118.4, 116.0, 69.4, 68.5, 30.9, 28.8, 28.7, 25.4, 24.0, 23.8, 23.0,18.6, 14.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium t-butanolate; In acetonitrile; at 50℃; for 24h;Inert atmosphere; Schlenk technique; | The ferrocenylphosphine-imidazolium salt 5-BF4 (200mg, 0.25 mmoles) was placed in dry, degassed MeCN (10mL) and <strong>[14592-56-4]PdCl2(MeCN)2</strong> (74.5mg, 0.29 mmoles) and tBuONa (30mg, 0.32 mmoles) were successively added. The mixture was heated at 50C for 24h, then the solvent was concentrated under reduced pressure. The residue was purified by flash column chromatography on silicagel (eluent: CH2Cl2/Acetone 95:5) to give a pale orange solid (243mg, 77% yield). 1H NMR (CDCl3, 400MHz, 298K): δ 8.04 (2H, dd, JHH=7.7Hz, JHP=12.1Hz, CH PPh2), 7.55-7.51 (1H, m, CH PPh2), 7.45 (2H, td, JHH=7.6Hz, JHP=2.6Hz, CH PPh2), 7.38-7.34 (1H, m, CH PPh2), 7.25 (2H, td, JHH=7.8Hz, JHP=2.5Hz, CH PPh2), 6.91-6.87 (2H, m, CH PPh2), 6.87 (1H, app. s, NCH=CH), 6.84 (1H, app. s, NCH=CH), 6.50 (1H, d, AB system, JHH=14.9Hz, CH2 Fc), 4.79-4.75 (2H, m, CpA+CH2 Fc), 4.44-4.39 (1H, m, CH2Im+), 4.39 (1H, t, JHH=2.7Hz, CH CpA) 4.36 (5H, s, CH CpB), 3.96 (1H, t, JHH=10.2Hz, CH2OSi(CH3)2C(CH3)3), 3.57 (1H, app. s, CH CpA), 3.51 (1H, dt, JHH=11.1Hz, 3.2Hz, CH2OSi(CH3)2C(CH3)3), 2.86 (1H, ddd, JHH=13.0Hz, 9.1Hz, 2.9Hz, CH2Im+), 0.83 (9H, s, CH2OSi(CH3)2C(CH3)3)), -0.01, -0.04 (2x3H, s, CH2OSi(CH3)2C(CH3)3). 13C{1H} NMR (CDCl3, 100.62MHz, 298K): δ 156.2 (d, JCP=9.9Hz, NCN), 136.0 (d, JCP=10.3Hz, CH PPh2), 134.9 (d, JCP=55.0Hz, Cq PPh2), 131.4 (d, JCP=2.9Hz, p-CHPPh2), 130.6 (d, JCP=11.3Hz, CH PPh2), 130.0 (d, JCP=2.0Hz, p-CH PPh2), 128.4 (d, JCP=10.5Hz, CH PPh2), 127.7 (d, JCP=55.1Hz, Cq PPh2), 127.6 (d, JCP=11.2Hz, CH PPh2), 123.6 (NCH=CH), 120.1 (NCH=CH), 87.1 (d, JCP=13.4Hz, Cq CpA), 74.3 (d, JCP=2.7Hz, CH CpA), 73.2 (d, JCP=6.6Hz, CH CpA), 71.4 (CpB), 70.9 (d, JCP=57.4Hz, Cq CpA), 70.1 (d, JCP=6.4Hz, CH CpA), 62.3 (CH2OSi(CH3)2C(CH3)3), 52.5 (CH2Im), 49.6 (CH2Fc), 25.8 (CH2OSi(CH3)2C(CH3)3), 18.0 (CH2OSi(CH3)2C(CH3)3), -5.4, -5.5 (2xCH2OSi(CH3)2C(CH3)3). 31P{1H} NMR (CDCl3, 161.99MHz, 298K): δ 4.4. MS (ESI) m/z 789 [M-Cl+Ca] (95), 767 [M-Cl+H2O] (100), 740 (68). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium phosphate; In 1,2-dichloro-ethane; at 80℃; for 2h;Inert atmosphere; | General procedure: 1 equivalent of Cl2Pd(MeCN)2 was added to a dry 1,2-dicloroethanesolution of the corresponding iminophosphorane (5 mL) and Na3PO4 inexcess under a nitrogen atmosphere. The solution was refluxed for 2 h.The solvent was removed under vacuum and the orange solid residueswere purified by flash chromatography (CH2Cl2/Hexane, 70:30). 3.3.8. Compound [PdCl{2-C8H5N(Ph2P=NC6H4SCH3- κ3-NNS)}] 658 mg of iminophosphorane 2 (0.132 mmol) and 34 mg(0.132 mmol) of (MeCN)2PdCl2. Yield mg 81 (%). M.p. 258-260 C(dec.). Anal. Calc. For C27H22N2P1S1Cl1Pd1 (578.0): C 55.97; H 3.83; N4.83. Found: C 56.01; H 3.87; N 4.80. MS (FAB+) 579 m/z (M+) 20%.IR (ν, cm-1): 1258.6 (νPN). 31P NMR (162 MHz, CDCl3, 20 C): δ 31.9;1H NMR (500 MHz, CDCl3, 20 C): δ 6.62 (s, H2), 7.48 (d, H4,3JH4H5=8 Hz), 6.96-6.91 (H5), 7.14 (dd, 1H6, 3J H6H5=7.5 Hz, 3JH6H7=8 Hz), 8.71 (d, H7, 3J H7H6=8 Hz), 6.64 (d, H10,3JH10H11=8.5 Hz), 6.91-6.95 (H11), 6.80 (dd, H12, 3JH12H11=7.5 Hz,3J H12H13=8 Hz), 7.30 (d, H13,3J H13H12=8 Hz), 2.85(s, 3H, SMe), 7.78-7.88 (m, 4H, Pho), 7.50-7.55 (m, 4H, Phm),7.61-7.68 (m, 2H, Php); 13C NMR (125 MHz, CDCl3, 20 C): δ 136.0 (s,C1), 110.7 (d, C2, 2JC2P=28 Hz), 129.5 (s, C3), 120.4 (s, C4), 119.1 (s,C5), 123.0 (s, C6), 118.0 (s, C7), 149.2 (s, C8), 153.3 (s, C9), 119.4 (d,C10, 3JC10P=8 Hz), 130.5 (s, C11), 120.8 (s, C12), 133.2 (s, C13), 126.2(s, C14), 28.2 (s, 1C, SMe), 129.5 (s, 2C, Phipso), 133.3 (d, 4C, Pho,2JCP=13 Hz), 129.6 (d, 4C, Phm,3JCP=12 Hz), 133.9 (d, 2C, Php,4JCP=7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium phosphate; In 1,2-dichloro-ethane; at 80℃; for 2h;Inert atmosphere; | General procedure: 1 equivalent of Cl2Pd(MeCN)2 was added to a dry 1,2-dicloroethanesolution of the corresponding iminophosphorane (5 mL) and Na3PO4 inexcess under a nitrogen atmosphere. The solution was refluxed for 2 h.The solvent was removed under vacuum and the orange solid residueswere purified by flash chromatography (CH2Cl2/Hexane, 70:30). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium phosphate; In 1,2-dichloro-ethane; at 80℃; for 2h;Inert atmosphere; | General procedure: 1 equivalent of Cl2Pd(MeCN)2 was added to a dry 1,2-dicloroethanesolution of the corresponding iminophosphorane (5 mL) and Na3PO4 inexcess under a nitrogen atmosphere. The solution was refluxed for 2 h.The solvent was removed under vacuum and the orange solid residueswere purified by flash chromatography (CH2Cl2/Hexane, 70:30). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium phosphate; In 1,2-dichloro-ethane; at 80℃; for 2h;Inert atmosphere; | General procedure: 1 equivalent of Cl2Pd(MeCN)2 was added to a dry 1,2-dicloroethanesolution of the corresponding iminophosphorane (5 mL) and Na3PO4 inexcess under a nitrogen atmosphere. The solution was refluxed for 2 h.The solvent was removed under vacuum and the orange solid residueswere purified by flash chromatography (CH2Cl2/Hexane, 70:30). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium acetate In acetonitrile at 25℃; for 18h; | Synthesis of [PdCI{4-[2-(2-hydroxyethoxy)=N{2,6JPr-C6H3}]2 (T3) T3 was synthesised by stirring a solution of bis(acetonitrile)palladium dichloride (0.100 g, 0.386 mmol) in acetonitrile (5.00 ml_). T2 (0.142 g, 0.386 mmol) and sodium acetate (0.063 g, 0.77 mmol) were added to the solution. The resulting orange mixture was stirred for 18 hours in an oil bath at ± 25 °C. The solvent was removed to obtain a yellow oily residue which was dissolved in DCM (50.0 ml_) and filtered through celite to remove any metallic palladium. The solvent volume was reduced and the solution was then layered with hexane at low temperature (-16 °C) to crystallise the product. The yellow crystalline solid was isolated by vacuum filtration and rinsed with hexane. The product was dried under vacuum. Yield: 0.156 g, 80%. FT-IR (VC=N, cm 1) 1597. m.p.: 150-154 °C. ESI-MS: [M-CI+2MeCN]+ 1065; [(M/2)-CI]2+ 474.1. Anal. Found: C, 53.6; H, 5.98; N, 2.36. Calc for C46Fl6oCl2N206Pd2: C, 54.1 ; H, 5.92; N, 2.74. |
With sodium acetate at 25℃; | 4.2.1. General procedure for μ-Cl palladacycle The μ-chloro bridged complex was synthesized by stirring a solutionof bis(acetonitrile)palladium dichloride (1 eq.) in acetonitrile (5.00 mL).The ligand (1 eq.) and sodium acetate (2 eq.) were added to the solution.The resulting red mixture was stirred for 18 h at 25 C. The solvent wasremoved, and the residue dissolved in DCM (50.0 mL) and filteredthrough celite to remove any metallic palladium. The filtrate volumewas reduced and layered with hexane at low temperature to solidify theproduct. The products were isolated by vacuum filtration, rinsed withhexane and dried under vacuum. | |
With sodium acetate at 25℃; | 4.2.1. General procedure for μ-Cl palladacycle The μ-chloro bridged complex was synthesized by stirring a solutionof bis(acetonitrile)palladium dichloride (1 eq.) in acetonitrile (5.00 mL).The ligand (1 eq.) and sodium acetate (2 eq.) were added to the solution.The resulting red mixture was stirred for 18 h at 25 C. The solvent wasremoved, and the residue dissolved in DCM (50.0 mL) and filteredthrough celite to remove any metallic palladium. The filtrate volumewas reduced and layered with hexane at low temperature to solidify theproduct. The products were isolated by vacuum filtration, rinsed withhexane and dried under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique; | 2.2.1 [{2,6-Bis(benzimidazol-2-yl)pyridine}PdCl]BF4 (PdL1) General procedure: To a solution of PdCl2(NCMe)2 (0.10g, 0.39mmol) in CH2Cl2 (30mL) was added L1 (0.12g, 0.39mmol) and NaBF4 (0.04, 0.39mmol) to give a yellow solution. The resultant mixture was stirred for 12 h and filtered through a short pad of Celite to remove the precipitate of NaCl. Hexane (10mL) was added to the filtrate to afford PdL1 as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique; | 2.2.1 [{2,6-Bis(benzimidazol-2-yl)pyridine}PdCl]BF4 (PdL1) To a solution of PdCl2(NCMe)2 (0.10g, 0.39mmol) in CH2Cl2 (30mL) was added L1 (0.12g, 0.39mmol) and NaBF4 (0.04, 0.39mmol) to give a yellow solution. The resultant mixture was stirred for 12 h and filtered through a short pad of Celite to remove the precipitate of NaCl. Hexane (10mL) was added to the filtrate to afford PdL1 as a yellow solid. Yield: 0.12g (57%). 1H NMR (400MHz, DMSO-d6): δH (ppm): 7.24-7.33 (m, 4H); 7.57 (d, 3JHH=8.1, 2H); 7.93 (d, 3JHH=8.1, 2H); 8.06 (d, 3JHH=8.0, 2H); 8.35 (t, 1H, 3JHH=7.9, H). 13C NMR (DMSO-d6): δC (ppm): 114.62; 116.73; 122.05; 124.91; 140.06; 142.87; 147.54; 152.97. FT-IR (cm-1): υ(N-H)=2728; υ(C=C)=1571; υ(C=N)=1476. TOF MS ES+, m/z (%)=451 [M, 100]+. HRMS-ESI [M+3H]+: m/z calc: 449.9738; found: 449.9730. Anal. calcd (%) for C19H13BClF4N5Pd: C, 42.26; H, 2.43; N, 12.97. Found (%): C, 41.95; H, 2.70; N, 12.71. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triethylamine; In chloroform-d1; at 20℃; for 24h;Schlenk technique; | Into a Schlenk tube, 13.7 mg (0.077 mmol) 1-phenyl-1H-tetrazole-5-thiol was added to 10 mg (0.038 mmol) of [<strong>[14592-56-4]PdCl2(MeCN)2</strong>] using 0.5 mLof CDCl3 as solvent. 25 μL (0.18 mmol) of Et3N was then added to the reaction mixture stirred for 24 h at room temperature. After the reactiontime had elapsed, the solvent was reduced in vacuo to yield the crudeproduct. The crude product obtained was washed with 1 mL diethyletherand subsequently washed with 1 mL H2O. The product was then dried invacuo for 6 h to yield (2) Appearance reddish brown solid, (Yield = 15.1mg, 81%). Solubility: soluble in chloroform; 1H NMR (400 MHz, CDCl3,30 0C) (ppm): 7.77 (d, 3J = 8 Hz, Harom), 7.53 (m, Harom); 13C{1H} NMR(100.6 MHz, CDCl3): 130.21; 129.46; 123.55; HR-ESI-MS [M 2tz]+ =566.1632; Elemental analysis; Anal. calcd. for C32H31N16Pd2S4: C,39.19%; H, 3.19%; N, 22.85%; S, 13.08%, Found C, 28.99%; H, 3.51%;N, 12.55%; S, 7.24%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,3‐bis[2,6‐bis(1‐propylbutyl)phenyl]‐4,5‐dichloro‐1H‐imidazolium chloride With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox; Stage #2: dichloro bis(acetonitrile) palladium(II) In tetrahydrofuran Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 40℃; for 4h; Inert atmosphere; Sealed tube; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In dichloromethane at 20℃; for 24h; | 2.2.2. Synthesis of Dichloro{bis-3,5-tert-buytl-1H-pyrazole}palladium(II) (2) L2 (139 mg, 0.771 mmol) and [PdCl2(NCMe)2] (100 mg,0.386 mmol) were dissolved in CH2Cl2 (20 mL), and then stirred continuously at room temperature for 24 h, affording an orange solution. This was followed by in vacuo removal of the solvent to produce compound 2 as a yellowish-orange solid. Yield: 150 mg(72 %); melting point: 220-224 °C (decompose without melting). 1HNMR(400MHz,CDCl3): δ (ppm) 1.00 (s, 2x9H,6xCH3); 1.76 (s,2x9H, 6xCH3); 5.82 (s, IH, 4-H pz); 11.65 (s, 1H, N-H) (Fig. SI-10).13C{1H} NMR (100 MHz, CDCl3) (ppm): 165.0 (Cf-C); 156.7(Ce-C); 101.7 (Cd-C); 32.4 (Cc-C); 31.1 (Cb-C); 30.0 (Ca-CH3)(Fig. SI-11). Elemental analysis; Anal. calcd. for C22H40Cl2N4Pd:C, 49.12 %;H, 7.50 %; N, 10.42 %. Found C: 48.92 %;H, 7.16 %, N,10.00 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In tetrahydrofuran for 3h; Inert atmosphere; Schlenk technique; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; for 10h; Overall yield = 90 percent; Overall yield = 422 mg; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96 % | In dichloromethane at 20℃; Inert atmosphere; | 9-(2-Mesityl-1H-indol-1-yl)-2-phenyl-9H-carbazole (rac-6m): N-(2-(mesitylethynyl)phenyl)-2-phenyl-9H-carbazol-9-amine 3m (19.1, 40.0 μmol, 1.00 eq.) and Pd(CH3CN)2Cl2 (2.08 mg, 8.00 μmol, 1.00 eq.) were dissolved in 10 mL of dry ethanol and the resulting mixture was stirred at 80°C for 48 h. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (cyclohexane/CH2Cl2 from 1:0 to 10:1) to give the title compound as a beige viscous solid (15.3 mg, 32.1 μmol, 80%): Rf 0.51 (cyclohexane/ CH2Cl2, 3:1); νmax (neat): 3055w, 3012w, 2959w, 2921w, 2860w, 1729w, 1609m, 1567w, 1484w, 1454s, 1312m, 1229m, 1150w, 1076w, 1037w, 907m, 853m, 803w, 735s, 697s; 1H NMR (500 MHz, CDCl3) δ = 8.07 (1H, d, 3J 8.1 Hz, C4'H), 8.05 - 8.02 (1H, m, C5'H), 7.76 - 7.73 (1H, m, C4H), 7.54 - 7.46 (3H, m, C3'H, C2'''H, C6'''H), 7.39 (2H, t, 3J 7.7 Hz, C3'''H, C5'''H), 7.32 - 7.26 (3H, C4'''H, C6'H, C7'H), 7.24 - 7.22 (1H, m, C1'H), 7.22 - 7.18 (1H, m, C5H), 7.05 - 6.97 (2H, m, C6H, C8'H), 6.72 (2H, d, 3J 6.7 Hz, C3''H, C5''H), 6.67 (1H, d, 4J 0.8 Hz, C3H), 6.51 - 6.47 (1H, m, C7H), 2.30 (3H, s, C2''-CH3), 2.22 (3H, s, C6''-CH3), 2.13 (3H, s, C4''-CH3); 13C NMR (126 MHz, CDCl3) δ = 141.4 (C1'''), 141.1 (C2'), 140.9 (C9a'), 139.4 (C8a'), 138.8 (C2), 138.7 (C6''), 138.6 (C2''), 138.4 (C4''), 136.3 (C7a), 128.7 (C3''', C5'''), 128.2 (C5''), 128.1 (C3''), 127.4 (C2''', C6'''), 127.2 (C4'''), 126.9 (C1''), 126.3 (C3a), 125.9 (C7'), 122.7 (C5), 121.6 (C4b'), 121.3 (C6 / C6'), 121.1 (C4a'), 120.9 (C4), 120.6 (C3'), 120.5 (C4'), 120.3 (C5'), 110.1 (C8'), 109.7 (C7), 108.4 (C1'), 104.2 (C3), 21.6 (C2''-CH3), 21.4 (C6''-CH3), 21.0 (C4''-CH3); ESI-MS: m/z calcd. for C35H29N2 477.2325 found 477.2318 [M+H+]. |
Tags: 14592-56-4 synthesis path| 14592-56-4 SDS| 14592-56-4 COA| 14592-56-4 purity| 14592-56-4 application| 14592-56-4 NMR| 14592-56-4 COA| 14592-56-4 structure
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