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[ CAS No. 5216-36-4 ] {[proInfo.proName]}

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Chemical Structure| 5216-36-4
Chemical Structure| 5216-36-4
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Product Details of [ 5216-36-4 ]

CAS No. :5216-36-4 MDL No. :MFCD00438701
Formula : C16H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 228.25 Pubchem ID :-
Synonyms :

Safety of [ 5216-36-4 ]

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:

Application In Synthesis of [ 5216-36-4 ]

* 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.

  • Downstream synthetic route of [ 5216-36-4 ]

[ 5216-36-4 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 5216-36-4 ]
  • [ 2510-73-8 ]
YieldReaction ConditionsOperation in experiment
With 1,4-dioxane; nickel at 60℃; Hydrogenation;
  • 2
  • [ 1820-42-4 ]
  • [ 544-92-3 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-pyrrolidin-2-one
  • 3
  • [ 7603-37-4 ]
  • [ 5216-36-4 ]
  • [ 78811-65-1 ]
YieldReaction ConditionsOperation in experiment
68% for 6h; Irradiation;
  • 4
  • [ 67013-55-2 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
92% With potassium hydroxide In dimethyl sulfoxide
  • 5
  • [ 421-20-5 ]
  • [ 5216-36-4 ]
  • N,N'-dimethyl-4,4'-diphenylacetylenedicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% at 65 - 70℃; for 6h;
  • 6
  • [ 223562-46-7 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;

  • 7
  • [ 66107-32-2 ]
  • [ 14630-40-1 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
86 % Chromat. With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 12h;
YieldReaction ConditionsOperation in experiment
With methanol; potassium hydroxide; ethanol
  • 9
  • 4-butynylbenzonitrile [ No CAS ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
93% With 4-nitro-phenol; CH3CH2CMo[N(t-Bu)(3,5-C6H3Me2)]3 In various solvent(s) at 30℃; for 22h;
  • 10
  • [ 5216-36-4 ]
  • hexakis(4-cyanophenyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dicobalt octacarbonyl In 1,4-dioxane at 110℃; for 18h;
  • 11
  • [ 623-00-7 ]
  • [ 3032-92-6 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;

  • 12
  • [ 5216-36-4 ]
  • C16H12N2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With ammonium sulfide In N,N-dimethyl-formamide at 20℃; for 0.5h;
  • 13
  • [ 104-85-8 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 51 percent / bromine / 1 h / 140 °C 2: 92 percent / KOH (s) / dimethylsulfoxide
  • 14
  • [ 623-00-7 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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

  • 15
  • [ 75867-40-2 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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
  • 16
  • [ 5216-36-4 ]
  • [ 5216-37-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Raney nickel; dioxane / 60 °C / 22065.2 Torr / Hydrogenation 2: nitrobenzene; iodine
  • 17
  • [ 5216-26-2 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Zn 2: 1-methyl-pyrrolidin-2-one
  • 18
  • [ 4137-78-4 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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
  • 19
  • [ 107-58-4 ]
  • [ 5216-36-4 ]
  • [ 1032285-63-4 ]
  • [ 1032285-45-2 ]
YieldReaction ConditionsOperation in experiment
1: 71.3 mg 2: 33.5 mg With tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 24h;
  • 20
  • [ 107-58-4 ]
  • [ 5216-36-4 ]
  • [ 1032285-45-2 ]
  • 21
  • [ 5216-36-4 ]
  • C16H8N2*2FHO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With fluorosulphonic acid at -80℃;
  • 22
  • [ 5216-36-4 ]
  • [ 1088706-06-2 ]
YieldReaction ConditionsOperation 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℃;
  • 23
  • [ 3058-39-7 ]
  • [ 14630-40-1 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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).
  • 24
  • [ 5216-36-4 ]
  • [ 2487-98-1 ]
  • [ 1192648-74-0 ]
  • 5,6-bis(4-cyanophenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 25
  • [ 1942-45-6 ]
  • [ 5216-36-4 ]
  • [ 1208341-99-4 ]
YieldReaction ConditionsOperation in experiment
46% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; Pyridine hydrobromide; triphenylphosphine In o-xylene for 6h; Inert atmosphere; Reflux; regioselective reaction;
  • 26
  • [ 5216-36-4 ]
  • [ 1208342-17-9 ]
YieldReaction ConditionsOperation 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;
  • 27
  • [ 5216-36-4 ]
  • [ 622-79-7 ]
  • [ 1259487-37-0 ]
YieldReaction ConditionsOperation 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;
  • 28
  • [ 59507-56-1 ]
  • p-cyanophenylzinc iodide-lithium chloride complex [ No CAS ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;
  • 29
  • [ 623-00-7 ]
  • [ 994-71-8 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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).
  • 30
  • [ 5216-36-4 ]
  • [ 1352657-86-3 ]
  • [ 1352657-93-2 ]
YieldReaction ConditionsOperation in experiment
45% With bis(tri-t-butylphosphine)palladium(0); sodium carbonate In N,N-dimethyl-formamide at 100℃; for 46h;
  • 31
  • [ 5216-36-4 ]
  • [ 17878-37-4 ]
  • [ 1374337-08-2 ]
YieldReaction ConditionsOperation 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;
  • 32
  • [ 5216-36-4 ]
  • C27H27N5O2*2ClH [ No CAS ]
YieldReaction ConditionsOperation 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
  • 33
  • [ 5216-36-4 ]
  • 1-phenyl-4,5-bis-(4-amidinophenyl)[1,2,3]triazole dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 34
  • [ 5216-36-4 ]
  • 1-benzyl-4,5-bis-(4-amidinophenyl)[1,2,3]triazole dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 35
  • [ 5216-36-4 ]
  • [ 1350432-03-9 ]
YieldReaction ConditionsOperation in experiment
65% With sodium azide In N,N-dimethyl-formamide at 170℃; for 6h; Inert atmosphere;
  • 36
  • [ 5216-36-4 ]
  • 4,5-bis-(4-amidinophenyl)[1,2,3]triazole dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 37
  • [ 5216-36-4 ]
  • [ 1350432-05-1 ]
YieldReaction ConditionsOperation 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
  • 38
  • [ 5216-36-4 ]
  • [ 1350432-06-2 ]
YieldReaction ConditionsOperation 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
  • 39
  • [ 5216-36-4 ]
  • 2-phenyl-4,5-bis-(4-amidinophenyl)[1,2,3]triazole dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 40
  • [ 5216-36-4 ]
  • 2-benzyl-4,5-bis-(4-amidinophenyl)[1,2,3]triazole dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 41
  • [ 5216-36-4 ]
  • C26H25N5O2*2ClH [ No CAS ]
YieldReaction ConditionsOperation 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
  • 42
  • [ 5216-36-4 ]
  • C27H27N5O2*2ClH [ No CAS ]
YieldReaction ConditionsOperation 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
  • 43
  • [ 5216-36-4 ]
  • C20H21N5O2*2ClH [ No CAS ]
YieldReaction ConditionsOperation 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
  • 44
  • [ 5216-36-4 ]
  • C26H25N5O2*2ClH [ No CAS ]
YieldReaction ConditionsOperation 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
  • 45
  • [ 5216-36-4 ]
  • [ 622-37-7 ]
  • [ 1350432-21-1 ]
YieldReaction ConditionsOperation in experiment
77% With copper(ll) sulfate pentahydrate; sodium carbonate; <i>L</i>-proline; ascorbic acid In water; dimethyl sulfoxide at 120℃; for 15h;
  • 46
  • [ 5216-36-4 ]
  • [{Ni(1,2-bis(dimethylphosphino)ethane)}2(μ-diphenylsilyl)2] [ No CAS ]
  • [ 1401083-30-4 ]
  • [ 1401083-31-5 ]
YieldReaction ConditionsOperation in experiment
1: 10% 2: 70 %Spectr. In toluene at 60℃; for 24h; Inert atmosphere;
  • 47
  • C14H16O2BCN [ No CAS ]
  • [ 3058-39-7 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
49% With 1,3-dimethyl-2-imidazolidinone; potassium carbonate; triphenylphosphine; copper(l) chloride at 120℃; for 12h;
  • 48
  • potassium (4-cyanophenyl)ethynyltrifluoroborate [ No CAS ]
  • [ 623-00-7 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;
  • 49
  • [ 5216-36-4 ]
  • [ 1227476-15-4 ]
  • 3,4-bis(p-cyanophenyl)-2-phenylcinnolinium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 50
  • [ 3058-39-7 ]
  • [ 3032-92-6 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;

  • 51
  • [ 478501-26-7 ]
  • [ 5216-36-4 ]
  • [ 1445990-49-7 ]
YieldReaction ConditionsOperation 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;
  • 52
  • [ 3469-20-3 ]
  • [ 5216-36-4 ]
  • 4,4′-(12-phenylindolo[2,1-a]isoquinoline-5,6-diyl)dibenzonitrile [ No CAS ]
  • 53
  • [ 105-07-7 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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
  • 54
  • [ 5216-36-4 ]
  • [ 61613-20-5 ]
  • C29H19N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; lithium chloride In acetonitrile at 100℃; for 2h; Microwave irradiation; Green chemistry;
  • 55
  • [ 5216-36-4 ]
  • [ 4105-21-9 ]
  • C29H16N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; copper diacetate In toluene at 110℃; for 12h;
  • 56
  • [ 170891-76-6 ]
  • [ 5216-36-4 ]
  • 4,5-bis(4-cyanophenyl)-2,2-dimethyl-N-(quinolin-8-yl)pent-4-enamide [ No CAS ]
  • 4,5-bis(4-cyanophenyl)-2,2-dimethyl-N-(quinolin-8-yl)pent-4-enamide [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 57
  • [ 5216-36-4 ]
  • 5,5'-[2,5-bis(2,2-dibromovinyl)-1,4-phenylene]bis(ethyne-2,1-diyl)}bis(1,3-ditert-butylbenzene) [ No CAS ]
  • 4,4',4'',4'''-[3,8-bis(3,5-di-tert-butylphenyl)dicyclopenta[a,g]-s-indacene-1,2,6,7-tetrayl]tetrabenzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 58
  • [ 5216-36-4 ]
  • 2,6-bis(2,2-dibromovinyl)-1,5-bis(phenylethynyl)naphthalene [ No CAS ]
  • 4,4',4'',4'''-(4,10-diphenyldipentaleno[1,2-a:1',2'-f]naphthalene-2,3,8,9-tetrayl)tetrabenzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 59
  • [ 3032-92-6 ]
  • [ 2252-32-6 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;
  • 60
  • [ 5216-36-4 ]
  • [ 826-42-6 ]
  • C24H17N3 [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 61
  • [ 1013-88-3 ]
  • [ 5216-36-4 ]
  • 4,4'-(1-phenylisoquinoline-3,4-diyl)dibenzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 62
  • [ 623-00-7 ]
  • [ 1066-54-2 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;
  • 63
  • [ 1066-54-2 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;
  • 64
  • [ 5216-36-4 ]
  • [ 775-12-2 ]
  • (E)-4,4'-(1-(diphenylsilyl)ethene-1,2-diyl)dibenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With bromopentacarbonylmanganese(I); triphenyl-arsane In toluene at 150℃; for 10h; Schlenk technique; Sealed tube; Inert atmosphere; stereoselective reaction;
  • 65
  • [ 5216-36-4 ]
  • triisopropylsilylethynyl ferrocenyl ether [ No CAS ]
  • C37H38FeN2OSi [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 66
  • [ 33757-48-1 ]
  • [ 5216-36-4 ]
  • C48H26N6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With bis(1,5-cyclooctadiene)nickel (0) at 150℃; for 24h;
  • 67
  • [ 5216-36-4 ]
  • [ 126213-50-1 ]
  • (E,E)-2,5-bis[1,2-di(4-cyanophenyl)ethenyl]-3,4-ethylenedioxythiophene [ No CAS ]
  • (E,Z)-2,5-bis[1,2-di(4-cyanophenyl)ethenyl]-3,4-ethylenedioxythiophene [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 68
  • [ 40473-50-5 ]
  • [ 5216-36-4 ]
  • C29H18N2O [ No CAS ]
YieldReaction ConditionsOperation 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%.
  • 69
  • [ 5216-36-4 ]
  • N‐(pyrimidin‐2‐yl)indoline [ No CAS ]
  • 4,4',4'',4'''-{1-(2-pyrimidinyl)-2,3-dihydro-1H-benzo[g]indole-6,7,8,9-tetrayl}tetrabenzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 70
  • [ 3058-39-7 ]
  • bis-pivaloyloxyzinc acetylide [ No CAS ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
50 mg With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 25℃; Inert atmosphere;
  • 71
  • [ 623-00-7 ]
  • bis-pivaloyloxyzinc acetylide [ No CAS ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
84% With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 25℃; for 12h; Inert atmosphere;
  • 72
  • [ 3058-39-7 ]
  • [ 1066-54-2 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation 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;
  • 73
  • [ 5216-36-4 ]
  • N-(2-cyanophenyl)-N-(2-fluorophenyl)-3-(3-methoxyphenyl)propanamide [ No CAS ]
  • (E)-3-(3-(1,2-bis(4-cyanophenyl)vinyl)-5-methoxyphenyl)-N-(2-cyanophenyl)-N-(2-fluorophenyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 74
  • [ 5216-36-4 ]
  • (E)-4,4’-(1,2-dibromoethene-1,2-diyl)dibenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With water; dibromoisocyanuric acid In acetonitrile at 25℃; for 16h;
  • 75
  • [ 5216-36-4 ]
  • [ 98-80-6 ]
  • 4,4',4'',4'''-(naphthalene-1,2,3,4-tetrayl)tetrabenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate In tert-Amyl alcohol; water at 80℃; for 12h; Electrochemical reaction; Inert atmosphere;
  • 76
  • [ 5216-36-4 ]
  • 1-iodo-3-((2-methylallyl)oxy)benzene [ No CAS ]
  • 4,4'-(2a-methyl-2a,3-dihydro-2H-naphtho[1,8-bc]furan-4,5-diyl)dibenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With cesium acetate; palladium diacetate In N,N-dimethyl-formamide at 90℃; for 24h; Sealed tube; Inert atmosphere;
  • 77
  • [ 1030366-99-4 ]
  • [ 5216-36-4 ]
  • 4,4',4'',4'''-(benzo[4',5']imidazo[1',2':1,6]pyrido[3,2-g]benzo[4,5]imidazo[1,2-a][1,8]naphthyridine-6,7,9,10-tetrayl)tetrabenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In toluene at 140℃; for 12h; Sealed tube;
  • 78
  • [ 1235527-62-4 ]
  • [ 5216-36-4 ]
  • C31H19N5 [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 79
  • [ 603-76-9 ]
  • [ 5216-36-4 ]
  • 4,4'-(5,12-dimethyl-5,12-dihydroindolo[3,2-a]carbazole-6,7-diyl)dibenzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 80
  • [ 79-41-4 ]
  • [ 5216-36-4 ]
  • 4,4'-(3-methyl-2-oxo-2H-pyran-5,6-diyl)dibenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; tetrabutylammonium acetate In methanol at 60℃; for 12h; Electrochemical reaction;
  • 81
  • [ 223562-46-7 ]
  • [ 503-17-3 ]
  • [ 5216-36-4 ]
YieldReaction ConditionsOperation in experiment
78% With C68H52MoO4Si3 In toluene at 60℃; for 12h; Molecular sieve; Inert atmosphere;
  • 82
  • [ 5216-36-4 ]
  • [ 19348-61-9 ]
  • 4,4'-(1-oxo-2-(quinolin-8-yl)-1,2-dihydroisoquinoline-3,4-diyl)dibenzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 83
  • [ 5216-36-4 ]
  • C8H6FO2(1-)*Li(1+) [ No CAS ]
  • C23H15FN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Ru(C6Me6)(OAc)2]; acetic acid In 1,2-dichloro-ethane at 100℃; for 24h; regioselective reaction;
  • 84
  • [ 5216-36-4 ]
  • methyl 2-(2-iodophenyl)-3-methyl-2H-isoindole-1-carboxylate [ No CAS ]
  • methyl 5,6-bis(4-cyanophenyl)-11-methyleneisoindolo[2,1-a]quinoline-6a(11H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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;
Same Skeleton Products
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