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CAS No. : | 79135-69-6 | MDL No. : | MFCD05864409 |
Formula : | C18H18 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MMGWBBCAKHJUPL-UHFFFAOYSA-N |
M.W : | 234.34 | Pubchem ID : | 12867281 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-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 diethyl ether; ammonia; potassium amide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl ether; ammonia; sodium amide | ||
Multi-step reaction with 2 steps 1: ethanolic KOH 2: KNH2; liquid NH3; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl ether; ammonia; sodium amide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 29 % Spectr. 2: 26 % Spectr. | With lithium aluminium tetrahydride; titanium(III) chloride In tetrahydrofuran for 25h; Heating; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In ethanol at 60℃; for 6h; other p,p'-dialkyldiphenylacetylenes, other metallic catalysts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With hydrogen In ethanol at 40 - 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium hydroxide for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With copper(l) iodide; diethylamine; triphenylphosphine; palladium dichloride at 54 - 55℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With hexacarbonyl molybdenum; hex-3-yne; 2-fluorophenol In chlorobenzene for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / hydrogen / Pd-CaCO3 / ethanol / 40 - 50 °C 2: iodine / light petroleum / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 100 percent / bromine / CCl4 / cold, dark conditions 2: 90 percent / 43 percent KOH in 95 percent ethanol / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 73% 2: 7% | Stage #1: methanol; 1-ethyl-4-[2-(4-ethylphenyl)-1-ethynyl]benzene With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor at 70℃; Stage #2: With triethylamine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With methanol; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor at 70℃; for 17h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dysprosium In N,N-dimethyl acetamide at 80℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With oxygen; palladium diacetate; triethylamine; copper(ll) bromide In acetic acid at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 4h; Inert atmosphere; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In water; benzene at 80℃; | ||
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine In tetrahydrofuran; triethylamine at 20℃; Inert atmosphere; Schlenk technique; |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In water; benzene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In tert-Amyl alcohol at 120℃; for 6h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.762 % de | With ferrous(II) sulfate heptahydrate; methanesulfonic acid; trifluoroacetic acid; naphthalene-1,8-diamine In 1,4-dioxane; water at 120℃; for 24h; Inert atmosphere; Overall yield = 73 %; Overall yield = 61.4 mg; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With ferrous(II) sulfate heptahydrate; methanesulfonic acid; trifluoroacetic acid; naphthalene-1,8-diamine In 1,4-dioxane; water at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With sodium pivalate; lithium bromide; palladium dichloride; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 30h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triiron dodecarbonyl In diethyl ether at 120℃; for 24h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With dipotassium peroxodisulfate In acetonitrile at 90℃; for 24h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With silver tetrafluoroborate; carbonyl(η-5-cyclopentadienyl)diiodocobalt(III); silver(I) acetate In 1,2-dichloro-ethane at 70℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 1-ethyl-4-[2-(4-ethylphenyl)-1-ethynyl]benzene With iodine In dimethyl sulfoxide at 130℃; for 24h; Stage #2: 2-amino-1-benzylamine With acetic acid In dimethyl sulfoxide at 100℃; for 20h; | 3 Synthesis of 2,3-bis (4-ethylphenyl)-5-1,4-benzodiazepine (Compound 3) To the reaction tube, followed by adding 10.1 mg of iodine, 46.8 mg of 1,2-bis(4-ethylphenyl)acetylene, 2mL dimethyl sulfoxide, the reaction was carried out in an oil bath at 130 °C for 24 hours, the reaction solution was cooled to room temperature, followed by the addition of 97.7 mg of 2-aminobenzylamine and 1 mL of acetic acid, and placed in an oil bath at 100 C for 20 hours, and finally subjected to conventional treatment to obtain 55.0 mg of compound 3, Yield 78%. |
78% | Stage #1: 1-ethyl-4-[2-(4-ethylphenyl)-1-ethynyl]benzene With iodine In dimethyl sulfoxide at 130℃; for 24h; Stage #2: 2-amino-1-benzylamine With acetic acid In dimethyl sulfoxide at 20 - 100℃; for 20h; | 2 Example 2 2,3-bis (4-ethylphenyl) -5-hydro-1,4-benzodiazepine (Compound 2) To the reaction tube, 10.1 mg of iodine, 46.8 mg of 1,2-bis (4-ethylphenyl) acetylene and 2 mL of dimethylsulfoxide were successively added and reacted in an oil bath at 130 ° C for 24 hours, At room temperature, followed by the addition of 97.7 mg of 2-aminobenzylamine and 1 mL of acetic acid, followed by reaction in an oil bath at 100 ° C for 20 hours. Finally, 55.0 mg of compound 2 was obtained by conventional treatment in a yield of 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With silver hexafluoroantimonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In para-xylene at 120℃; for 24h; Inert atmosphere; Sealed tube; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88 % ee | With bis(1,5-cyclooctadiene)nickel(0); (3aS,8aS)-2,2-dimethyl-4,4,8,8-tetra(naphthalen-2-yl)tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 6-oxide; trimethylaluminum; XPhos In hexane; 1,3,5-trimethyl-benzene at 130℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Overall yield = 93 %; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 80℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With trichloroisocyanuric acid; water In acetonitrile at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With 2-phenylpyridine; lithium carbonate; copper(II) bis(trifluoromethanesulfonate); silver carbonate In 1,2-dichloro-ethane at 130℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 1,4-diaza-bicyclo[2.2.2]octane; sodium carbonate; palladium dichloride In N,N-dimethyl-formamide at 130℃; for 12h; Schlenk technique; | 2 Example 2: Synthesis of Compound 3ab 0.025 mmol PdCl2, 0.05 mmol DABCO, 0.6 mmol sodium carbonate, 0.5 mmol of triazole starting material 1a, 0.6 mmol of substituted diphenylacetylene 2b and 1.5 mL of DMF were sequentially added to a 25 mL Schelenk bottle, vacuumed and replaced with nitrogen. Three times, the Schelenk bottle was placed in a 130 ° C oil bath and stirred for 12 h, the heating was stopped, and the temperature of the reaction system was lowered to the chamber. After heating, the colorless transparent crystal product 3ab was isolated by column chromatography, and the eluent was petroleum ether/ethyl acetate (volume ratio)10:1), the structure of the compound was tested by nuclear magnetic 1H NMR, 13C NMR and mass spectrometry. Colorless transparent crystal, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With [RhCl2(p-cymene)]2; potassium acetate; sodium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube; | 4.2. General procedure for ruthenium-catalyzed annulation of 1,3-diphenylacetone with internal alkynes General procedure: A 25mL sealed tube was charged with 1,3-diphenylacetone 1a(0.2 mmol, 2.0 equiv), internal alkynes 2 (0.1 mmol, 1.0 equiv),[RuCl2(p-cymene)]2 (0.015 mmol, 15 mol%), KOAc (0.2 mmol, 2.0equiv), Na2CO3 (0.2 mmol, 2.0 equiv) and PhMe (0.5 mL). The vialwas evacuated and filled with N2 atmosphere, and stirred at 100 Cfor 24 h. After being cooled to room temperature, the mixture wasevaporated under reduced pressure. The residue was purified byflash column chromatography on silica gel, eluting with petroleumether to afford the desired products 3. |
54% | With [RhCl2(p-cymene)]2; potassium acetate; sodium carbonate In toluene at 100℃; for 24h; Sealed tube; Inert atmosphere; | 4 Example 4 Add dibenzyl ketone (42mg, 0.2mmol) to a 25mL sealed tube with magnets,The corresponding internal alkynes (0.1 mmol),Catalyst [RuCl2(p-cymene)]2 (9mg, 15%mol),0.5mL toluene, then add dry sodium carbonate (21mg, 0.2mmol),Potassium acetate (19mg, 0.2mmol),Purge nitrogen three times, react at 100°C for 24 hours,Then it is separated by column chromatography (eluent: petroleum ether) to obtain the target compound.The characterization is as follows. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With water; dibromoisocyanuric acid In acetonitrile at 75℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.091 % de | With cobalt(II) aceylacetonate; nickel(II) acetylacetonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 150℃; for 24h; Inert atmosphere; Overall yield = 91 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In ethanol; 1,2-dichloro-ethane at 100℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With decacarbonyldirhenium(0); bis(μ-diphenylamido)-bis(methylzinc); zinc trifluoromethanesulfonate In toluene at 150℃; for 72h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-bis((R)-1-(3,5-dimethylphenyl)ethyl)-4-methylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium <i>tert</i>-butylate; isopropyl alcohol In tetrahydrofuran at 60℃; for 18h; Inert atmosphere; Glovebox; Sealed tube; Green chemistry; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium <i>tert</i>-butylate; isopropyl alcohol In tetrahydrofuran at 100℃; for 18h; Inert atmosphere; Glovebox; Sealed tube; Green chemistry; | |
72% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium <i>tert</i>-butylate In tetrahydrofuran; isopropyl alcohol at 100℃; for 18h; Inert atmosphere; Green chemistry; | 22 Example 22:Synthesis of (E) -N- (2,3-bis (4-ethylphenyl) -1-phenylallyl) -4-methylbenzenesulfonamide Under a nitrogen atmosphere, the ligand AnIPr.HCl (5.5 mg, 5 mol%), t-BuOK (2.3 mg, 10 mol%) were sequentially added to the reaction flask.Ni (cod) 2 (5.5mg, 10mol%), THF (1.0mL), i-PrOH (1.0mL),Finally, raw materials 1e (47 mg, 0, 2 mmol) and 2a (62 mg, 0.24 mmol) were added.Stir at 100 ° C for 18 hours, cool to room temperature, and dilute with ethyl acetate.Filtered through diatomaceous earth and concentrated to obtain the target product 4d after column chromatography.White solid, yield (72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper diacetate In N,N-dimethyl-formamide at 100℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In dichloromethane at 20℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate at 100℃; for 15h; Glovebox; Inert atmosphere; Schlenk technique; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-bis((R)-1-(3,5-dimethylphenyl)ethyl)-4-methylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium <i>tert</i>-butylate In tetrahydrofuran; isopropyl alcohol at 60℃; for 18h; Inert atmosphere; Green chemistry; | 35 Example 35:Synthesis of (S, E) -N- (1- (4- (Diethylamino) phenyl) -2,3-bis (4-ethylphenyl) allyl) -4-methylbenzenesulfonamide Under a nitrogen atmosphere, the ligand AnIPr-1 (9.4 mg, 10 mol%), t-BuOK (1.4 mg, 12 mol%), Ni (cod) 2 (2.8 mg, 10 mol%), and THF were sequentially added to the reaction flask. (1.5mL), i-PrOH (1.5mL),Finally, raw materials 1e (23.4 mg, 0.1 mmol) and 2s (39.6 mg, 0.12 mmol) were added.Stir at 60 ° C for 18 hours, cool to room temperature, and dilute with ethyl acetate.Filter through diatomaceous earth and concentrate to isolate the target product 5d after column chromatography.White solid, yield (60%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; tetrabutylammonium acetate In methanol at 60℃; for 12h; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; sodium acetate In ethanol at 60℃; for 12h; Inert atmosphere; Green chemistry; | To a 13 × 150 mm test tube equipped with magnetic stir bar were added [RhCp*(CH3CN)3](SbF6)2 (6.6mg, 4 mol %), NaOAc (32.8mg, 0.4 mmol, 2 equiv) and 2a-2o (0.3 mmol, 1.5 equiv). The test tube was sealed with a rubber septum and removed from the glove-box. The solution of 1a-1r (0.2 mmol, 1 equiv)in EtOH (2 mL) was injected into the test tube via syringe. The reaction mixture was placed in a preheated oil bath (60 ) for 12 h. Then the reaction mixture was concentrated in vacuo, the residue was dissolved in methylene chloride and purified by column chromatography (silica gel, n-hexane/EtOAc =20/1). 1-Methyl-3,4-diphenylisoquinoline (3aa): The title compound was obtained as white crystal in 91% yield (54.2 mg). 1H NMR (400 MHz, CDCl3) δ 8.24 - 8.16(m, 1H), 7.66 (m, 1H), 7.63 - 7.55 (m, 2H), 7.41 - 7.28 (m, 5H), 7.26 - 7.12 (m,5H), 3.09 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 157.78, 149.37, 140.90, 137.56,136.06, 131.44, 130.32, 130.04, 129.29, 128.24, 127.66, 127.18, 127.01, 126.62,126.29, 126.19, 125.60, 22.73. HRMS (EI) calcd. for C22H17N: [M]+, 295.1361. Found: m/z 295.1358. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium acetate In 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With diisopropylsulfide; 3,4,5-trimethylbenzoic acid; copper diacetate; palladium diacetate; silver carbonate In toluene at 160℃; for 3h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0); phenylsilane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine In N,N-dimethyl-formamide at 80℃; for 12h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With chlorocarbonylbis(triphenylphosphine)rhodium(I) In chlorobenzene for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; manganese(II) acetate dihydrate; potassium <i>tert</i>-butylate In 1,2-dichloro-ethane; acetonitrile at 40℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis(acetylacetonate)nickel(II); 3,4,7,8-Tetramethyl-o-phenanthrolin; methoxybenzene; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; cobalt acetylacetonate at 155℃; for 18h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); water; sodium iodide at 20℃; for 5h; | (21) Diarylethynes 2a-r: General Procedure General procedure: The appropriate aryldiazonium tetrafluoroborate 1 (0.4 mmol),CaC2 (77 mg, 1.2 mmol), Pd(PPh3)4 (23 mg, 0.02 mmol), CuI (8mg, 0.04 mmol), NaI (180 mg, 1.2 mmol), and H2O (173 mg, 9.6mmol) in DES (1:2 choline chloride-urea) (4 mL) were stirred atr.t. for 5 h. When the reaction was complete (TLC), H2O (2 mL)and EtOAc (2 mL) were added. The resulting mixture was subjectedto ultrasonication for 5 min, then filtered to removesolids. The liquor was extracted with EtOAc (3 × 10 mL), and theextracts were washed with saturated brine (3 × 10 mL). Theresulting organic phase was dried (Na2SO4) and concentratedunder reduced pressure. The residue was purified by columnchromatography (silica gel, PE-EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.947 % de | With N-chlorophthalimide; ferrous sulfate hydrate; trifluorormethanesulfonic acid; water In fluorobenzene at 90℃; for 12h; Overall yield = 83 percent; Overall yield = 56 mg; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 80℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: 1-ethyl-4-[2-(4-ethylphenyl)-1-ethynyl]benzene; N-phenylbenzamidine With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; tetrabutyl ammonium fluoride; copper diacetate; Trimethylacetic acid In 1,2-dichloro-ethane; toluene at 80℃; for 48h; Stage #2: With bis-[(trifluoroacetoxy)iodo]benzene In 2,2,2-trifluoroethanol; 1,2-dichloro-ethane; toluene at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; tetrabutylammonium acetate In methanol at 60℃; for 12h; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With palladium diacetate; caesium carbonate; triphenylphosphine In toluene at 80℃; for 48h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With bis(1,5-cyclooctadiene)nickel (0); trimethylaluminum; (3aR,7aR)-2,3,3a,4,5,6,7,7a-Octahydro-1,3-bis(2,2-dimethylpropyl)-1H-1,2,3-benzodiazaphosphole-2-oxide In hexane; toluene at 80℃; for 12h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: diiron nonacarbonyl; potassium <i>tert</i>-butylate / tetrahydrofuran / 12 h / 75 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: silver(I) triflimide / 1,2-dichloro-benzene / 24 h / 170 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: diiron nonacarbonyl; potassium <i>tert</i>-butylate / tetrahydrofuran / 12 h / 75 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: silver(I) triflimide / 1,2-dichloro-benzene / 24 h / 170 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: diiron nonacarbonyl; potassium <i>tert</i>-butylate / tetrahydrofuran / 12 h / 75 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: silver(I) triflimide / 1,2-dichloro-benzene / 24 h / 170 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Stage #1: 1-ethyl-4-[2-(4-ethylphenyl)-1-ethynyl]benzene With diiron nonacarbonyl; potassium <i>tert</i>-butylate In tetrahydrofuran at 75℃; for 12h; Inert atmosphere; Stage #2: acetone With copper(II) choride dihydrate In tetrahydrofuran Inert atmosphere; | General procedure for the synthesis of cyclobutenedione General procedure: THF (150 mL) was addedto a mixture of Fe2(CO)9 (5.457 g, 15.00 mmol) and t-BuOK (2.245 g, 20.00 mmol) at roomtemperature under argon. The resulting mixture was stirred for 0.5 h at room temperatureand another 15 min at 65 °C. Diphenylacetylene (0.892 g, 5.00 mmol) was added andthen further stirred for 12 h at 75 °C. The mixture was cooled to room temperature,and CuCl2*2H2O (12.786 g, 75.00 mmol) in acetone (50 mL) was added. After filtration,the filtrate was concentrated under reduced pressure. The residue was purified by flashchromatography (petrol ether/EtOAc = 20:1) to give products. TheNMRdata are consistentwith previous reports in the literature (1a [32,37], 1b, 1d, 1f-1h [37], 1e [38]). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid In dichloromethane at 23℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With silver hexafluoroantimonate; C52H52Cl4O4Rh2; acetic acid In dichloromethane at 23℃; for 12h; enantioselective reaction; |