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CAS No. : | 5216-36-4 | MDL No. : | MFCD00438701 |
Formula : | C16H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 228.25 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 1,4-dioxane; nickel at 60℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-methyl-pyrrolidin-2-one |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | for 6h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium hydroxide In dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | at 65 - 70℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With Mo(≡CPh)(OSiPh3)3(biphy); manganese(ll) chloride In toluene at 20 - 80℃; Inert atmosphere; Molecular sieve; | |
80% | With tris[N-(tert-butyl)(3,5-dimethylphenyl)amido]molybdenum(VI) propylidyne; tris(2-hydroxy-3-isopropylbenzyl)methane In tetrachloromethane at 40℃; for 12h; Molecular sieve; Inert atmosphere; Glovebox; | |
77% | With C68H52MoO4Si3 In toluene at 60℃; for 14h; Inert atmosphere; Molecular sieve; |
58% | With dichloromethane In toluene | |
58% | With dichloromethane In toluene at 80℃; | |
37% | With 2-(trifluoromethyl)phenol; CH3CH2CMo[N(t-Bu)(3,5-C6H3Me2)]3 In various solvent(s) at 30℃; for 22h; | |
15% | In various solvent(s) at 140℃; | |
26 %Chromat. | With (p-OMe-C6H4C≡)Mo(OCMe(CF3)2)3-(1,3-di(isopropyl)imidazol-2-ylidene)complex on silica650 In toluene at 20℃; for 4h; Molecular sieve; Inert atmosphere; Schlenk technique; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86 % Chromat. | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; potassium hydroxide; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 4-nitro-phenol; CH3CH2CMo[N(t-Bu)(3,5-C6H3Me2)]3 In various solvent(s) at 30℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dicobalt octacarbonyl In 1,4-dioxane at 110℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper(l) iodide; [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride; triethylamine; triphenylphosphine at 100℃; for 2h; Inert atmosphere; | |
49% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In benzene at 70℃; for 16h; | |
24% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In benzene for 16h; Reflux; |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In benzene at 70℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With ammonium sulfide In N,N-dimethyl-formamide at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 51 percent / bromine / 1 h / 140 °C 2: 92 percent / KOH (s) / dimethylsulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / CuI; triethylamine; PdCl2(PPh3)2 / benzene / 16 h / 70 °C 2: 89 percent / K2CO3; MeOH / CH2Cl2 / 0.5 h / 20 °C 3: 49 percent / CuI; triethylamine; PdCl2(PPh3)2 / benzene / 16 h / 70 °C | ||
Multi-step reaction with 2 steps 1: 85 percent / ZnBr2; Pd(PPh3)4 / tetrahydrofuran / 4 h / 60 °C 2: 37 percent / CH3CH2CMo[N(t-Bu)(3,5-C6H3Me2)]3; α,α,α-trifluoro-o-cresol / various solvent(s) / 22 h / 30 °C / 5 Torr | ||
Multi-step reaction with 2 steps 1: 93 percent / ZnBr2; Pd(PPh3)4 / tetrahydrofuran / 4 h / 60 °C 2: 93 percent / CH3CH2CMo[N(t-Bu)(3,5-C6H3Me2)]3; p-nitrophenol / various solvent(s) / 22 h / 30 °C / 1 Torr |
Multi-step reaction with 2 steps 1: 26 percent / triethylamine; CuI / Pd(PPh3)2Cl2 / 24 deg C, then 65 deg C 2: 15 percent / Mo(CO)6, 4-chlorophenol / various solvent(s) / 140 °C | ||
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / benzene / 16 h / 70 °C 2: potassium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / benzene / 16 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 89 percent / K2CO3; MeOH / CH2Cl2 / 0.5 h / 20 °C 2: 49 percent / CuI; triethylamine; PdCl2(PPh3)2 / benzene / 16 h / 70 °C | ||
Multi-step reaction with 2 steps 1: potassium carbonate / methanol; dichloromethane / 1 h / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Raney nickel; dioxane / 60 °C / 22065.2 Torr / Hydrogenation 2: nitrobenzene; iodine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Zn 2: 1-methyl-pyrrolidin-2-one |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: KI 2: Zn 3: 1-methyl-pyrrolidin-2-one | ||
Multi-step reaction with 2 steps 1: Zn 2: 1-methyl-pyrrolidin-2-one |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 71.3 mg 2: 33.5 mg | With tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With fluorosulphonic acid at -80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: 4,4'-ethynediyl-di-benzonitrile With fluorosulphonic acid; lead dioxide at -50℃; for 2.5h; Stage #2: With hydrogenchloride In water at -60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 6h; | |
72% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; | 4.4. General procedure for synthesis of symmetrically disubstituted ethynes by the reaction of bis(trimethylsilyl)ethyne with 2 equiv of aryl iodides. Di(4-cyanophenyl)ethyne (6b)56 To a solution of Pd(PPh3)4 (116 mg, 0.1 mmol), CuCl (99 mg, 1 mmol), and 4-iodobenzonitrile (2c) (458 mg, 2 mmol) in DMF (8 mL) in a 20 mL of Schlenk tube was added bis(trimethylsilyl)ethyne (5) (0.23 mL, 1 mmol) at rt. The reaction mixture was stirred for 6 h at 80 °C before quenching with 1 M HCl and extracted with diethyl ether (20 mL×3). The combined layers were washed with brine and dried over MgSO4. Filtration and evaporation gave a brown solid, which was purified by column chromatography (silica gel, hexane/ethyl acetate=9:1; Rf=0.21) to give the titled compound (164 mg, 0.72 mmol, 72% yield) as white solid. 1H NMR (300 MHz, CDCl3, rt): δ 7.61-7.69 (m, 8H). MS (EI, m/z (relative intensity)): 228 (M+, 100), 201 (10), 175 (5), 151 (5), 114 (5), 101 (3), 87 (5), 74 (5), 63 (2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methyl 3-pyridinecarboxylate; chlorobis(ethylene)rhodium(I) dimer; O,O'-[(R)-3,3'-bis(trimethylsilyl)-1,1'-binaphthyl-2,2'-diyl]-N,N-dimethylphosphoramidite In toluene at 110℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; Pyridine hydrobromide; triphenylphosphine In o-xylene for 6h; Inert atmosphere; Reflux; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With 4-methyltetrahydropyran; C51H78N3OPPtSi4 at 130℃; for 20h; Glovebox; Inert atmosphere; Sealed tube; | |
46% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; Pyridine hydrobromide; triphenylphosphine In o-xylene for 6h; Inert atmosphere; Reflux; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In benzene at 80℃; for 3h; Inert atmosphere; | |
60% | With copper(ll) sulfate pentahydrate; sodium carbonate; <i>L</i>-proline; ascorbic acid In water; dimethyl sulfoxide at 120℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: 1,2-bis(methylthio)acetylene With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran for 0.166667h; Inert atmosphere; Stage #2: p-cyanophenylzinc iodide-lithium chloride complex In tetrahydrofuran at 50℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; | Bis(4-benzonitrilyl)acetylene (8).6 Tetrakis(triphenylphosphino) palladium(0) (60 mg, 1.6 mol%), triphenylphosphine (8 mg, 0.9 mol%), 4-bromobenzonitrile (1.27 g, 6.98 mmol, 2.10 eq.), 1 (2.01 g, 3.32 mmol) and p-dioxane (25 mL) were combined in a Schlenk flask and heated to 100 °C for 2 h. The volume was reduced to 20 mL in vacuo and the solid was filtered and washed with cold hexanes. The resulting solid was combined with hexanes (15 mL), heated to reflux for 5 minutes, cooled to room temperature and filtered, resulting in a white solid, compound 8 (0.62 g, 74%). m. p.: 249-251 °C. 1H NMR (CDCl3; 300.17 MHz): d 7.65 (dd, J = 15.7 Hz, J = 9.4 Hz) 13C NMR (CDCl3; 75.485 MHz): d 132.2 (C-H), 131.8 (C-H), 127.1, 118.2, 112.5 (nitrile), 91.6 (acetylene). UV/Vis (toluene): lmax 324 nm (e = 48,800), 303 nm (e = 63,400). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With bis(tri-t-butylphosphine)palladium(0); sodium carbonate In N,N-dimethyl-formamide at 100℃; for 46h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With bis(η3-allyl-μ-chloropalladium(II)); tri-tert-butylphosphine; 4-nitrobenzaldehdye; lithium tert-butoxide In toluene at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 6 h / 170 °C / Inert atmosphere 2: tetra-(n-butyl)ammonium iodide; potassium carbonate / acetone / 20 h / 70 °C / Inert atmosphere 3: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: copper(ll) sulfate pentahydrate; sodium carbonate; <i>L</i>-proline; ascorbic acid / water; dimethyl sulfoxide / 15 h / 120 °C 2.1: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere 3.1: ammonia / ethanol / 24 h / 20 °C / Inert atmosphere 3.2: 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: copper(ll) sulfate pentahydrate; sodium carbonate; <i>L</i>-proline; ascorbic acid / water; dimethyl sulfoxide / 15 h / 120 °C 2.1: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere 3.1: ammonia / ethanol / 24 h / 20 °C / Inert atmosphere 3.2: 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium azide In N,N-dimethyl-formamide at 170℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium azide / N,N-dimethyl-formamide / 6 h / 170 °C / Inert atmosphere 2.1: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere 3.1: ammonia / ethanol / 24 h / 20 °C / Inert atmosphere 3.2: 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 6 h / 170 °C / Inert atmosphere 2: iron(III)-acetylacetonate; caesium carbonate; copper(II) oxide / N,N-dimethyl-formamide / 30 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 6 h / 170 °C / Inert atmosphere 2: tetra-(n-butyl)ammonium iodide; potassium carbonate / acetone / 20 h / 70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium azide / N,N-dimethyl-formamide / 6 h / 170 °C / Inert atmosphere 2.1: iron(III)-acetylacetonate; caesium carbonate; copper(II) oxide / N,N-dimethyl-formamide / 30 h / 90 °C / Inert atmosphere 3.1: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere 4.1: ammonia / ethanol / 24 h / 20 °C / Inert atmosphere 4.2: 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium azide / N,N-dimethyl-formamide / 6 h / 170 °C / Inert atmosphere 2.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / acetone / 20 h / 70 °C / Inert atmosphere 3.1: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere 4.1: ammonia / ethanol / 24 h / 20 °C / Inert atmosphere 4.2: 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(ll) sulfate pentahydrate; sodium carbonate; <i>L</i>-proline; ascorbic acid / water; dimethyl sulfoxide / 15 h / 120 °C 2: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(ll) sulfate pentahydrate; sodium carbonate; <i>L</i>-proline; ascorbic acid / water; dimethyl sulfoxide / 15 h / 120 °C 2: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 6 h / 170 °C / Inert atmosphere 2: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 6 h / 170 °C / Inert atmosphere 2: iron(III)-acetylacetonate; caesium carbonate; copper(II) oxide / N,N-dimethyl-formamide / 30 h / 90 °C / Inert atmosphere 3: hydrogenchloride / 168 h / 20 °C / Cooling with ice; sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(ll) sulfate pentahydrate; sodium carbonate; <i>L</i>-proline; ascorbic acid In water; dimethyl sulfoxide at 120℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 10% 2: 70 %Spectr. | In toluene at 60℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With 1,3-dimethyl-2-imidazolidinone; potassium carbonate; triphenylphosphine; copper(l) chloride at 120℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-ethyl-N,N-diisopropylamine In water; isopropyl alcohol at 100℃; for 0.333333h; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium tetrafluoroborate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; silver carbonate In tert-Amyl alcohol at 110℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine at 20℃; for 15h; Inert atmosphere; | |
42% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Inert atmosphere; | |
41% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In tetrahydrofuran at 40℃; for 24h; Inert atmosphere; |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 100℃; for 2h; Microwave irradiation; | ||
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In dimethyl sulfoxide at 50℃; for 4h; Schlenk technique; Inert atmosphere; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine In tetrahydrofuran; triethylamine at 20℃; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With tri-tert-butyl phosphine; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; cesium pivalate In 1,4-dioxane at 140℃; for 48h; Glovebox; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 0.75 h / 60 °C / Microwave irradiation 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / acetonitrile / 2 h / 100 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; lithium chloride In acetonitrile at 100℃; for 2h; Microwave irradiation; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; copper diacetate In toluene at 110℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.538 % de | With nickel diacetate; triphenylphosphine In isopropyl alcohol; toluene at 170℃; for 24h; Inert atmosphere; Sealed tube; Schlenk technique; Overall yield = 70 %; Overall yield = 64 mg; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | Stage #1: 4,4'-ethynediyl-di-benzonitrile; 5,5'-[2,5-bis(2,2-dibromovinyl)-1,4-phenylene]bis(ethyne-2,1-diyl)}bis(1,3-ditert-butylbenzene) With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; zinc In toluene at 110℃; Schlenk technique; Inert atmosphere; Stage #2: In toluene at 110℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | Stage #1: 4,4'-ethynediyl-di-benzonitrile; 2,6-bis(2,2-dibromovinyl)-1,5-bis(phenylethynyl)naphthalene With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; zinc In toluene at 110℃; Schlenk technique; Inert atmosphere; Stage #2: In toluene at 110℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; chloro[tris(para-methoxyphenyl)phosphine]gold(I) In N,N-dimethyl-formamide at 20℃; for 1h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With silver tetrafluoroborate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; mesitylenecarboxylic acid In <i>tert</i>-butyl alcohol at 115℃; for 10h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With cerium(IV) sulphate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; potassium acetate; silver trifluoromethanesulfonate In nitromethane at 100℃; for 36h; Schlenk technique; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With iodo(4,5-bis(diphenylphosphano)-9,9-dimethylxanthene)copper(I); palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 20℃; for 18h; Inert atmosphere; Schlenk technique; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bromopentacarbonylmanganese(I); triphenyl-arsane In toluene at 150℃; for 10h; Schlenk technique; Sealed tube; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With palladium diacetate; triphenylphosphine; zinc In toluene at 90℃; for 6h; Inert atmosphere; Glovebox; | General Procedure for the Palladium-Catalyzed CH Activation/Cyclization of Alkynyl Ferrocenyl Ethers 1 with Alkynes 2. General procedure: In a dry box under an argon atmosphere, Pd(OAc)2,(5.6 mg, 0.025mmol), PCy3 (14 mg, 0.050mmol), Zn (1.6 mg,0.025mmol) and toluene (0.50 mL) were placed in a vial, thenthe mixture was stirred for 10min. Alkynyl ferrocenyl ether 1(0.50mmol) and alkyne 2 (0.55mmol) were added. After thevial was closed with a screw cap and taken outside the dry box,the reaction mixture was stirred at 90 °C for 6 h. For isolation,the crude was passed through an alumina plug, followedby recrystallization from dichloromethane/methanol to providethe corresponding ferrocene-fused pyran derivatives 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis(1,5-cyclooctadiene)nickel (0) at 150℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,2-dimethylbutyric acid; Pd{dba(OMe)}2; tricyclohexylphosphine In 1,4-dioxane at 120℃; for 24h; Inert atmosphere; Overall yield = 72 %; | Palladium-catalyzed intermolecular double-hydroarylation of 2a with 1a. General procedure: A general procedure for theformation of 3. Substrate 1a (70 mg, 0.49 mmol) and 2a (267 mg, 1.5 mmol) were added sequentially to asolution of Pd{dba(OMe)}2 (20 mg, 0.025 mmol), PCy3 (14 mg, 0.050 mmol), and t-AmylCO2H (5.8 mg,0.048 mmol) in 1,4-dioxane (0.5 mL) prepared in a 3 mL-vial in a dry box. The vial was closed with a screwcap, taken outside the dry box, and stirred at 120 °C for 20 h. The reaction mixture was filtered throughCelite, and the filtrate was evaporated and dried in vacuo. The crude was purified by recrystallization fromCH2Cl2 and hexane and flash chromatography using hexane and ethyl acetate (hexane : ethyl acetate =100:0 to 85:15 graduent) to give 3aa as a mixture of EE-, EZ-, and ZZ-forms (86:14:<1) in 86% yield (211mg, 0.42 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 6h; | 7 Example 7 A 100 mL round bottom flask was charged with 2.00 g (10 mmol) of compound I-6, 4.56 g (20 mmol) of compound II-2, 0.98 g (1 mmol) of solid Sc(OTf) 3, and finally 40 mL of dried 1,2-dichloroethane. The alkane was stirred vigorously for 6 hours at 80°C. The reaction mixture was cooled to room temperature, poured into water, stirred and extracted with 50 mL of dichloromethane. The organic phase was combined and extracted. The organic phase was washed once with saturated brine and dried over anhydrous Na2SO4 . The solvent was evaporated on a rotary evaporator to give an oily residue. Purification by column chromatography gave the pure product of Compound III-5. White solid, 3.49 g, yield 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1-methyl-pyrrolidin-2-one at 120℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction; | 2. The representative procedure for the synthesis of compounds 3 General procedure: A flame-dried Schlenk tube was cooled to ambient temperature and filled with N2. To this tube were added 1-(2-pyrimidinyl)indoline (1a) (98.5 mg, 0.5 mmol, 1.0 equiv.), diphenylacetylene (2a) (195.8 mg, 1.1 mmol), [Cp*RhCl2]2 (12.4 mg, 0.02 mmol), AgSbF6 (27.5 mg, 0.08 mmol), Cu(OAc)2 (181.5 mg, 1.0 mmol) and NMP (2.0 mL). Then the tube was heated at 120 °C. After 12 h, the reaction mixture was cooled to ambient temperature, diluted with sat. aq. NH4Cl/NH3(1:1, 50 mL) and extracted with EtOAc (3 x 50 mL). The organic layer was washed by brine (50 mL), then separated, driedover Na2SO4 and filtered. The solvents were removed under reduced pressure. The residue was purified by silica gel columnchromatography (PE/EtOAc/DCM = 20:1:1→10:1:1) to afford the desired product 3aa (213 mg, 77%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50 mg | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 25℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; benzene at 60℃; Inert atmosphere; Sealed tube; | |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 60℃; for 18h; Inert atmosphere; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 20℃; for 18h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silver hexafluoroantimonate; silver orthophosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; propionic acid In 1,2-dichloro-ethane at 120℃; for 48h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With water; dibromoisocyanuric acid In acetonitrile at 25℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate In tert-Amyl alcohol; water at 80℃; for 12h; Electrochemical reaction; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With cesium acetate; palladium diacetate In N,N-dimethyl-formamide at 90℃; for 24h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In toluene at 140℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With acetic acid; triethylamine In N,N-dimethyl-formamide at 110℃; for 36h; Inert atmosphere; | 4.1 General procedure for Pd/Cu-BNP catalyzed synthesis of polycyclic triazoles General procedure: Under the open atmosphere, 1,2,3-triazole 3 (0.25mmol), diaryl acetylene 4 (1.5 equiv.), 2.5mol% of Pd/Cu-BNP (10wt% Pd and 5wt% Cu by ICP-OES analysis) and DMF (1.5mL) were successively added to oven dried reaction tube. Then Et3N (1.5mmol) and AcOH (50mol%) were added and closed with a glass-stopper. The reaction tube was then immersed in pre-heated oil bath with magnetic pellet and stirred at 110°C. The reaction was heated with stirring till complete consumption 3. After cooling down to room temperature, the solvent was removed under reduced pressure. Water was added to the reaction mixture and extracted with ethyl acetate (3×5mL). Brine wash (1×10mL) was given to the combined organic extractions and dried over anhydrous Na2SO4. Removal of solvent and silica gel column separation of crude using hexanes and ethyl acetate mixture (4:1) afforded the corresponding tricyclic triazoles 5a-w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With oxygen; palladium diacetate; copper(II) acetate monohydrate In dimethyl sulfoxide at 50℃; for 24h; Schlenk technique; | 4.2. General procedure (GP) for the domino synthesis of indolo [3,2-a]carbazoles 3 General procedure: Palladium(II)acetate (11.2 mg, 50.0 μmol, 10 mol%), copper(II)acetate monohydrate (24.9 mg, 125 μmol, 25 mol%), indole 1(500 μmol, 1.00 equiv) and/or alkyne 2 (250 μmol, 0.50 equivs), ifsolid, were placed in a Schlenk tube, which was evacuated and flushedwith oxygen three times. Then, indole 1 (500 μmol, 1.00 eq.) and/oralkyne 2 (250 μmol, 0.50 equivs), if present as a liquid, and DMSO(5 mL) were added. The reaction mixture was stirred until completeconversion (8 or 24 h, monitored by TLC, eluent: n-hexane/ethylacetate) at 50 °C under an oxygen atmosphere. After cooling to roomtemp, the solvent was removed under reduced pressure, the productmixture adsorbed on Celite and purified by column chromatographyon silica gel (eluent: n-hexane/dichloromethane) See Table 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; tetrabutylammonium acetate In methanol at 60℃; for 12h; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With C68H52MoO4Si3 In toluene at 60℃; for 12h; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With tris(o-methoxyphenyl)phosphine; silver carbonate; cobalt(II) iodide In 1,2-dichloro-benzene at 130℃; for 24h; Sealed tube; Glovebox; Inert atmosphere; regioselective reaction; | |
54% | With chlorobis(ethylene)rhodium(I) dimer In 1,2-dichloro-ethane at 40℃; for 36h; Glovebox; Irradiation; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [Ru(C6Me6)(OAc)2]; acetic acid In 1,2-dichloro-ethane at 100℃; for 24h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 12h; Schlenk technique; |