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CAS No. : | 25677-69-4 | MDL No. : | MFCD00044208 |
Formula : | C24H16N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HVCVRVKEIKXBIF-UHFFFAOYSA-N |
M.W : | 332.40 | Pubchem ID : | 11186609 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With phosphoric acid; orthoarsenic acid at 135℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 1,10-Phenanthroline; phenyllithium In toluene at 0℃; Inert atmosphere; Stage #2: With manganese(IV) oxide In dichloromethane | Synthesis of 2-subsituted-1,10-phenanthrolines from 1,10-phenanthroline. General procedure: A solution of 1,10-phenanthroline (1 g) in dry, degassed toluene (200 ml) was cooled to 0 °C under argon and subjected to vigorous stirring. The pre-titrated n-butyl- or phenyllithium solution was added dropwise via syringe in the following way: on addition of the first few drops of alkylating reagent, no permanent color change was observed. On further careful addition (typically one drop) the solution became intensely colored, indicating formation of the addition product. From this point 1.0 equiv of lithium reagent was added slowly and the solution left to stir for 5 min. Quenching with H2O (30 ml), extraction with CH2Cl2 (3 × 100 ml) and reoxidation by MnO2 gave the title product. Work-up by filtration of the CH2Cl2 solution through a short plug of alumina and additional washing with CH2Cl2 (2 × 100 ml) gave, after removal of the solvent, the 2-substututed-1,10-phenanthroline in good yields (2-phenyl-1,10-phenanthroline: 99% and 2-butyl-1,10-phenanthroline: 98%, as white powders). |
78% | Stage #1: 1,10-Phenanthroline; phenyllithium In hexane; toluene at 0 - 25℃; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: With manganese(IV) oxide In toluene for 6h; Inert atmosphere; Schlenk technique; Glovebox; | |
38% | Stage #1: 1,10-Phenanthroline; phenyllithium In dibutyl ether; toluene at 0 - 20℃; Stage #2: With manganese(IV) oxide In dichloromethane for 2h; |
Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium permanganate; sodium periodate | ||
With potassium permanganate; sodium periodate; potassium carbonate In water; <i>tert</i>-butyl alcohol for 14h; Heating; | ||
With potassium permanganate; sodium periodate; potassium carbonate In water; <i>tert</i>-butyl alcohol for 14h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; boric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium cyanoborohydride; acetic acid In methanol for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 63 percent / acetic acid; NaBH3CN / methanol / 6 h / Heating 2: PCl3; N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 3: N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 4: S8 / CH2Cl2 / 0.42 h / Heating 5: 77 percent / LiAlH4 / tetrahydrofuran / 1.67 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 63 percent / acetic acid; NaBH3CN / methanol / 6 h / Heating 2: PCl3; N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 3: N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 4: S8 / CH2Cl2 / 0.42 h / Heating 5: 41 percent / LiAlH4 / tetrahydrofuran / 0.75 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 63 percent / acetic acid; NaBH3CN / methanol / 6 h / Heating 2: PCl3; N,N-dimethylaniline / CH2Cl2 / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 63 percent / acetic acid; NaBH3CN / methanol / 6 h / Heating 2: PCl3; N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 3: N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 4: S8 / CH2Cl2 / 0.42 h / Heating 5: 77 percent / LiAlH4 / tetrahydrofuran / 1.67 h / Heating 6: 75 percent / HCl / 3 h / 80 °C 7: 56 percent / S8; sodium hydride / tetrahydrofuran / 0.83 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 63 percent / acetic acid; NaBH3CN / methanol / 6 h / Heating 2: PCl3; N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 3: N,N-dimethylaniline / CH2Cl2 / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 63 percent / acetic acid; NaBH3CN / methanol / 6 h / Heating 2: PCl3; N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 3: N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 4: S8 / CH2Cl2 / 0.42 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 63 percent / acetic acid; NaBH3CN / methanol / 6 h / Heating 2: PCl3; N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 3: N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 4: S8 / CH2Cl2 / 0.42 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 63 percent / acetic acid; NaBH3CN / methanol / 6 h / Heating 2: PCl3; N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 3: N,N-dimethylaniline / CH2Cl2 / 1 h / Heating 4: S8 / CH2Cl2 / 0.42 h / Heating 5: 77 percent / LiAlH4 / tetrahydrofuran / 1.67 h / Heating 6: 75 percent / HCl / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; sodium periodate; potassium permanganate / 2-methyl-propan-2-ol; H2O / 14 h / Heating 2: 1.99 g / diethyl ether 3: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C | ||
Multi-step reaction with 3 steps 1: potassium permanganate; sodium periodate; potassium carbonate / H2O; 2-methyl-propan-2-ol / 14 h / Heating 2: 35 percent / diethyl ether 3: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; sodium periodate; potassium permanganate / 2-methyl-propan-2-ol; H2O / 14 h / Heating 2: 1.99 g / diethyl ether | ||
Multi-step reaction with 2 steps 1: potassium permanganate; sodium periodate; potassium carbonate / H2O; 2-methyl-propan-2-ol / 14 h / Heating 2: 35 percent / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate; sodium periodate; potassium permanganate / 2-methyl-propan-2-ol; H2O / 14 h / Heating 2.1: 1.99 g / diethyl ether 3.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C 4.1: triethylamine / CHCl3 / 24 h / 20 °C 4.2: 75 percent / toluene / 48 h / Heating 5.1: 71 percent / m-chloroperbenzoic acid / CH2Cl2 / 64 h / 20 °C 6.1: 98 percent / aq. NaOH / methanol / 31 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: potassium permanganate; sodium periodate; potassium carbonate / H2O; 2-methyl-propan-2-ol / 14 h / Heating 2.1: 35 percent / diethyl ether 3.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C 4.1: triethylamine / CHCl3 / 24 h / 20 °C 4.2: 75 percent / toluene / 48 h / Heating 5.1: 71 percent / m-chloroperbenzoic acid / CH2Cl2 / 64 h / 20 °C 6.1: 98 percent / sodium hydroxide / methanol; H2O / 31 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate; sodium periodate; potassium permanganate / 2-methyl-propan-2-ol; H2O / 14 h / Heating 2.1: 1.99 g / diethyl ether 3.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C 4.1: triethylamine / CHCl3 / 24 h / 20 °C 4.2: 75 percent / toluene / 48 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate; sodium periodate; potassium permanganate / 2-methyl-propan-2-ol; H2O / 14 h / Heating 2.1: 1.99 g / diethyl ether 3.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C 4.1: triethylamine / CHCl3 / 24 h / 20 °C 4.2: 75 percent / toluene / 48 h / Heating 5.1: 71 percent / m-chloroperbenzoic acid / CH2Cl2 / 64 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate; sodium periodate; potassium permanganate / 2-methyl-propan-2-ol; H2O / 14 h / Heating 2.1: 1.99 g / diethyl ether 3.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C 4.1: triethylamine / CHCl3 / 24 h / 20 °C 4.2: 75 percent / toluene / 48 h / Heating 5.1: 71 percent / m-chloroperbenzoic acid / CH2Cl2 / 64 h / 20 °C 6.1: 85 percent / aq. NaOH / methanol / 31 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium permanganate; sodium periodate; potassium carbonate / H2O; 2-methyl-propan-2-ol / 14 h / Heating 2.1: 35 percent / diethyl ether 3.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C 4.1: triethylamine / CHCl3 / 24 h / 20 °C 4.2: 75 percent / toluene / 48 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: potassium permanganate; sodium periodate; potassium carbonate / H2O; 2-methyl-propan-2-ol / 14 h / Heating 2.1: 35 percent / diethyl ether 3.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C 4.1: triethylamine / CHCl3 / 24 h / 20 °C 4.2: 75 percent / toluene / 48 h / Heating 5.1: 71 percent / m-chloroperbenzoic acid / CH2Cl2 / 64 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.2% | With chloro(6-phenyl-2,2'-bipyridine)platinum In 2-ethoxy-ethanol for 3h; Heating / reflux; | 7 Example 7 Production of platinum complex (1b''-9) ((2,9-diphenyl-1,10-phenanthrolinato-C,N,N)platinum (II) chloride) [(1,2,5,6-η4)-1,5-hexadienyl]platinum(II) dichloride (500 mg, 1.44 mmol, 1.0 equivalent) and 2,9-diphenyl-1,10-phenanthroline (574 mg, 1.72 mmol, 1.2 equivalents) were charged into a schlenk flask, whose inside was replaced with nitrogen. Then, 2-ethoxyethanol (10 mL) was added thereto, and the mixture was heated, and allowed to react with stirring under reflux for 3 hours. Then, the solvent was distilled off under reduced pressure. The resulting red orange residue was purified with a silica gel column chromatography (eluent: dichloromethane / methanol = 100/1), and then recrystallized from hexane / dichloromethane. As a result, 706 mg of the platinum complex (1b''-9) was obtained as a red orange powder. Yield 87.2 %. 1H-NMR(500MHz CD2Cl2) :δ 7.11 (dt, J=1.3, 7.4Hz, 1H), 7.16-7.24(m, 1H), 7.49-7.58(m, 4H), 7.63-7.77(m, 1H), 7.80-7.91(m, 5H), 7.96(d, J=8.5Hz, 1H), 8.42(d, J=8.6Hz, 1H), 8.50(d, J=8.5Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12.7% | In acetic acid at 80℃; for 48h; | 20 To 0.23 g of pentafluorophenyl(1,5-cyclooctadiene)platinum (II) chloride synthesized in the same manner as with (2) of Example 17, and 0. 59 g of 2, 9-diphenylphenanthroline, 20 ml of acetic acid was added. The mixture was stirred at 80 °C for 2 days. The resulting orange solution was concentrated under reduced pressure, and purified by a silica gel column chromatography (eluent: toluene / chloroform = 1 / 1). As a result, 0.04 g of the platinum complex (1'''-12) was obtained as an orange solid. Yield: 12.7 %. 1H-NMR(CD2Cl2) δ:6.70-6.53(m, 1H), 6.96(dt, J=1.4, 7.4Hz, 1 H),7.02(dt, J=1.3, 7.3Hz, 1H), 7.16-7.22(m, 3H), 7.45-7.47(m, 2 H),7.57(dd, J=7.6, 1.6Hz, 1H), 7.80(d, J=8.4Hz, 1H), 7.89-7.93 (m,2H),7.97(d, J=8.9Hz, 1H), 8.45(d, J=8.7Hz, 1H), 8.51(d, J=8. 4Hz,lH)ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; water; acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In dichloromethane; acetonitrile (under Ar); addn. of the ligand in CH2Cl2 to a soln. of the starting complex in acetonitrile at room temp., stirring for 2 h; solvent is evapd., solid is dissolved in ethanol, filtn., crystn. in a refrigerator, recrystn.(ethanol), elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile refluxing mixt. (1:1) of CuCl and dpp in CH3CN for 36 h; soln. cooling, volume redn. (argon) on crystn., crystal filtration; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide prepared in situ, addn. of 3 equiv. of ligand; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In not given Pd-complex dissolved at 0°C, addn. AgBF4 (immediate formation white ppt.), mixt. kept 20 min, addn. of the phenanthroline, mixt. stirred (20°C, 1h); filtered (Pasteur pipet, cotton plug and Celite column), evapn., recrystn. (CH2Cl2/Et2O); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | In acetonitrile byproducts: 2,5-diphenylphenanthrolinium(1+), Cl(1-), AgCl; refluxing stoich. amts. of phenanthroline derivative and KAuCl4 with 2 equiv. Ag-tosylate (72 h); concn., filtration, extn. of ppt. (boiling MeCN), crystn. on Et2O diffusion into extract; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile byproducts: 2,5-diphenylphenanthrolinium(1+), Cl(1-), AgCl; refluxing stoich. amts. of phenanthroline derivative and KAuCl4 with 2 equiv. AgClO4 (72 h); concn., filtration, extn. of ppt. (boiling MeCN), crystn. on Et2O diffusion into extract; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | In acetonitrile the starting complex is added to a refluxing ligand soln. in acetonirile, refluxed for 1 d; filtd., diffusion of diethyl ether into the filtrate, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With LiCl In methanol; ethanol Hg-salt and the org. compound refluxed for 6 h in EtOH, LiCl in MeOH added, refluxed for 30 min; hot filtered, cooled to room temp., filtered out, washed (ethyl acetate); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | In ethylene glycol other Radiation; heating Ru-complex with 1 equiv. substituted phenanthroline (70 W microwave oven, Ar-atmosphere, 30 min), cooling, addn. of excess aq. NH4PF6, stirring at room temp. for 1 h; pptn. on water addn., chromy. (Al2O3, PhMe/MeCN=2:1); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In acetonitrile Ar-atmosphere; addn. of 2 equiv. of phen derivative to Cu-complex soln.,stirring for 10 min; pptn. on Et2O addn., filtration, dissoln. in CH2Cl2, crystn. on layeringwith Et2O; elem. anal.; | |
86% | In methanol for 1h; Inert atmosphere; | |
50% | In dichloromethane; acetonitrile at 20℃; for 1h; Inert atmosphere; |
50.1% | In dichloromethane at 20℃; Inert atmosphere; | |
In dichloromethane; acetonitrile N2-atmosphere; addn. of 2 equiv. ligand (in 25% CH2Cl2 in MeCN) to Cu-complex, stirring at room temp. for 30 min; evapn., recrystn. (CH2Cl2/Et2O); | ||
In acetonitrile Ar-atmosphere; stirring stoich. amts. for 10 min; evapn., dissoln. in CH2Cl2, crystn. on layering with Et2O; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In ethylene glycol reflux (3 h) of soln. of Ru complex and phenanthroline, cooling to room temp.; filtration, addn. of satd. aq. K(PF6) (100°C), cooling, crystn. (0°C, overnight), filtration, washing (water), drying (air), chromy. (silica gel, CH3CN/water/satd. aq. NaNO3 (100:5:0.5)), anion exchangewith K(PF6); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol stirring stoich. amts. at room temp. for 2 h; crystn. in freezer overnight; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In N,N-dimethyl-formamide reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; water reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In dichloromethane organic ligand and anhydrous CuBr refluxed in CH2Cl2 for 2 h;; diethyl ether added to the CH2Cl2 solution; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In dichloromethane organic ligand and anhydrous CuBr2 stirred in CH2Cl2 at room temp.; after filtration solution slowly evaporated; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In tetrahydrofuran (N2); 2,9-diphenyl-1,10-phenanthroline and NiCl2*6H2O in THF were refluxed for 8 h; filtered, washed with EtOH, Et2O, recrystd. from CH2Cl2, elem. anal.; | |
50% | In ethanol under N2, a slight excess of Ni-compd. soln. was added to N-compd. soln., stirring at room temp. for 9 h; soln. was removed, ppt. was filtered off, washed with Et2O, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In ethanol under N2, a slight excess of Ni-compd. soln. was added to N-compd. soln., stirring at room temp. for 9 h; soln. was removed, ppt. was filtered off, washed with Et2O, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In chloroform to stirred suspn. Pt complex in CHCl3 was added ligand, suspn. was heated to reflux for 24 h; ppt. was collected by filtration, washed with Et2O, dried in air; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.1% | In tetrahydrofuran (N2); 2,9-diphenyl-1,10-phenanthroline and NiBr2*6H2O in THF were refluxed for 8 h; filtered, washed with EtOH, Et2O, recrystd. from CH2Cl2, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.5% | In tetrahydrofuran (N2); 2,9-diphenyl-1,10-phenanthroline and CoCl2*6H2O in THF were refluxed for 8 h; filtered, washed with EtOH, Et2O, recrystd. from CH2Cl2/CH3CN, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In acetone Ar; ligands dissolved in acetone, Cu compd. (1:1:1 molar ratio) added. stirred at room temp. for 2 h; ppt. filtered off, recrystd. (acetone/Et2O), filtered off, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene (N2); a soln. of Cu compd. added to a soln. of ligands, stirred; filtered, evapd., recrystd. from toluene/hexane at -30°C; obtained impure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In not given byproducts: C6H5CHCH2; under vac.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | In diethyl ether (N2); a flask charged with ligands and Cu compd., Et2O added, stirred; filtered, evapd., washed (hexane), dried (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.9% | In tetrahydrofuran (N2), ligand and Cu salt (1:1) stirred in THF for 8 h; filtered; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.5% | In dichloromethane (N2), ligand and Cu salt (1:1) stirred in Ch2Cl2 for 8 h; filtered, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloromethane 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: tetrakis(2-phenylquinoline-C2,N')(μ-dichloro)diiridium(III); 2,9-diphenyl-1,10-phenanthroline In methanol; dichloromethane Inert atmosphere; Reflux; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87 % ee | Stage #1: 2,9-diphenyl-1,10-phenanthroline With Ru(trifluoromethanesulfonate)(N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine)(η6-cymene); hydrogen In methanol at 25℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: at 25℃; for 12h; Overall yield = 90 %; Overall yield = 100 %Spectr.; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: nitrobenzene / 120 °C 2: potassium hexacyanoferrate(III); sodium hydroxide / water / 0 °C 3: trichlorophosphate; phosphorus pentachloride / 110 °C 4: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / water; toluene / 5 h / 100 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: phosphorus tribromide / nitrobenzene / 5.5 h / 170 °C 2: cesium fluoride; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 48 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hexacyanoferrate(III); sodium hydroxide / water / 0 °C 2: trichlorophosphate; phosphorus pentachloride / 110 °C 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / water; toluene / 5 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro bis(acetonitrile) palladium(II) In chloroform; acetonitrile at 60℃; for 13h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In water; toluene at 100℃; for 5h; Inert atmosphere; | |
46% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 48h; Schlenk technique; Reflux; | 2.6. General synthesis of phenanthroline ligands General procedure: Diaryl-substituted phenanthrolines were prepared by combining thedihalo-substituted phenanthroline with the appropriate phenylboronicacid in a 100 mL Schlenk flask. The solids were suspended in 30 mL oftoluene and 20 mL of 2 M Na2CO3(aq), then purged with Ar for 15 min.Subsequently, Pd(PPh3)4 (0.175 g, 0.15 mmol) was added to the flask,purged for an additional 15 min, then heated at reflux under Ar whilerapidly stirring. After 48 h, the biphasic mixture was cooled to roomtemperature and the two layers were isolated. The aqueous layer waswashed with dichloromethane and all organic fractions were combined,dried using anhydrous MgSO4, and filtered. The solvent was removedby rotary evaporation, and the solids were recrystallized with minimaltoluene followed by vacuum filtration. If necessary, the volume of theresulting filtrate was reduced and hexanes added to induce precipitation.The mixture was vacuum filtered and resulting white solids were collected. 2.6.1. 2,9-Diphenyl-1,10-phenanthroline (Ph2phen) [43]Starting materials: 2,9-dichloro-1,10-phenanthroline (0.250 g,1.00 mmol), phenyl boronic acid (0.428 g, 3.51 mmol), Pd(PPh3)4(0.175 g, 0.150 mmol). Yield = 0.153 g (0.460 mmol, 46%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate; phosphorus pentachloride / 110 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / water; toluene / 5 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; dichloromethane at 20℃; for 144h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: [{Ir(μ-Cl)(2-(p-tolyl)pyridinato)2}2]; 2,9-diphenyl-1,10-phenanthroline In methanol; dichloromethane Inert atmosphere; Reflux; Stage #2: ammonium hexafluorophosphate In water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.5% | Stage #1: [iridium(III)(μ-chloro)(2-phenylpyridine)2]2; 2,9-diphenyl-1,10-phenanthroline In ethylene glycol for 16h; Reflux; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water Inert atmosphere; | Synthesis of [Ir(ppy)2(dmphen)]PF6 (complex 1) General procedure: [Ir(ppy)2Cl]2 (0.069 g, 0.064 mmol)and 2,9-dimethyl-1,10-penanthroline (0.027 mg, 0.128 mmol) were heated to reflux in an ethylene glycol solution (20 ml) for 16 h. The mixture was transferred into a separation funnel with water (90 ml) and washed through three extractions with diethyl ether (60 ml).A concentrated solution of ammonium hexafluorophosphate in water was slowly added intothe aqueous layer, yielding a colored suspension. The precipitate was collected by filtration[13] |
Stage #1: [iridium(III)(μ-chloro)(2-phenylpyridine)2]2; 2,9-diphenyl-1,10-phenanthroline In methanol; dichloromethane Inert atmosphere; Reflux; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane; water Inert atmosphere; |
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 |
---|---|---|
58% | Stage #1: bis[μ-chloro-bis(2-phenylisoquinolinato-C2,N)iridium(III)]; 2,9-diphenyl-1,10-phenanthroline In methanol; dichloromethane Reflux; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | Stage #1: In toluene at 0 - 20℃; for 15h; Inert atmosphere; Stage #2: With manganese(IV) oxide In dichloromethane | 2.2.8 2.2 Synthesis of 2,9-di-sec-butyl-1,10-phenanthroline (di-sec-butylphen) (1) General procedure: Compound 1 was synthesized as previously described [ 13] by reacting an anhydrous toluene solution of 1,10-phenanthroline (1.00 g, 4.23 mmol) with sec-butyl-lithium (12.84 ml of 1.45 M, 16.92 mmol). The reaction was stirred at 0° C. under an argon atmosphere and the alkyl-lithium reagent was added in a drop-wise fashion over a 20 minute period. This solution was allowed to stir at room temperature for an additional 15 hours under an inert atmosphere. The reaction mixture was then quenched with H2O (30.0 ml) and the organic layer separated. The aqueous layer was extracted three times with CH2Cl2 (20.0 mL), and the combined organic layers were treated with excess MnO2 (15.0 g). This reaction mixture was stirred overnight and then gravity filtered through celite. This amber filtrate was dried with MgSO4, gravity filtered, and the solvent was removed by rotary evaporation to yield an amber oil. The crude oil was purified by flash chromatography (basic alumina; 100% hexane wash; elution with 20% CH2Cl2 in hexanes) to yield a pale yellow/white solid. 1H NMR chemical shifts, peak multiplicities and peak integrations, and the UV-vis absorption maxima have been previously reported [13]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-((1R,2R)-2-amino-1,2-diphenylethyl)-3,5-bis(trifluoromethyl)benzenesulfonamide; formic acid; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In isopropyl alcohol at 40℃; for 24h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: [iridium(III)(μ-chloro)(2-phenylpyridine)2]2; 2,9-diphenyl-1,10-phenanthroline In methanol; dichloromethane for 6h; Reflux; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With ammonium peroxydisulfate; benzaldehyde In ethyl acetate at 30℃; for 24h; Irradiation; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In dichloromethane at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: cis-dichlorobis(2,2'-bipyridyl)ruthenium(II); 2,9-diphenyl-1,10-phenanthroline In ethylene glycol for 6h; Reflux; Inert atmosphere; Stage #2: potassium hexafluorophosphate In ethylene glycol Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In toluene for 6h; Schlenk technique; Inert atmosphere; Darkness; Reflux; | 2.7. General synthesis of Re(I)-phenanthroline complexes General procedure: Re(R2phen) complexes were prepared by combining Re(CO)5Cl,diaryl-substituted phenanthrolines, and 5 mL toluene in a 50 mLSchlenk flask. The mixture was purged with Ar for 15 min prior toheating at reflux in the dark. After 6 h, the yellow mixture was cooled toroom temperature and 25 mL of hexanes were added to induce furtherprecipitation. The yellow solids were collected by vacuum filtration andrinsed with hexanes. 2.7.1. fac-[Re(Ph2phen)(CO)3Cl] (Re(Ph2phen)) [46]Starting materials: Re(CO)5Cl (0.050 g, 0.14 mmol), Ph2phen(0.045 g, 0.14 mmol). Yellow solid; yield = 0.049 g (0.077 mmol,56%). 1H NMR (500 MHz, 298 K, CDCl3): δ (ppm) = 8.57 (d, 2H,J = 8.3 Hz), 8.06 (s, 2H), 7.94 (d, 2H, J = 8.3 Hz), 7.82-7.74 (broadsinglet, 4H), 7.62-7.58 (m, 6H). FTIR (CH2Cl2) ν(CO): 2024 cm-1,1924 cm-1, 1888 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | Stage #1: 2,9-diphenyl-1,10-phenanthroline; copper dichloride In ethanol at 20℃; for 1.5h; Inert atmosphere; Stage #2: bis(trifluoromethane)sulfonimide lithium In ethanol; water for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: copper(l) iodide; 2,9-diphenyl-1,10-phenanthroline In ethanol at 20℃; for 1h; Inert atmosphere; Stage #2: bis(trifluoromethane)sulfonimide lithium In ethanol for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.3% | Stage #1: silver tetrafluoroborate; C21H17ClN4Pd In dichloromethane; acetone at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: 2,9-diphenyl-1,10-phenanthroline; C8H12CuIN4(1+)*BF4(1-) In dichloromethane; acetone at 0℃; for 20h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.9% | In nitromethane; acetonitrile at 0℃; for 20h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.6% | Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,9-diphenyl-1,10-phenanthroline In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: C49H35BF2N6 In dichloromethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.3% | With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dimethoxyethane at 100℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane-d2 at 24.84℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100 %Spectr. | In dichloromethane-d2 |