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[ CAS No. 5216-31-9 ] {[proInfo.proName]}

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Chemical Structure| 5216-31-9
Chemical Structure| 5216-31-9
Structure of 5216-31-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5216-31-9 ]

CAS No. :5216-31-9 MDL No. :MFCD01596894
Formula : C14H8F2 Boiling Point : -
Linear Structure Formula :- InChI Key :HFFUXLCRPYMGFM-UHFFFAOYSA-N
M.W : 214.21 Pubchem ID :5240533
Synonyms :

Calculated chemistry of [ 5216-31-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.78
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.07
Log Po/w (XLOGP3) : 4.14
Log Po/w (WLOGP) : 4.28
Log Po/w (MLOGP) : 5.12
Log Po/w (SILICOS-IT) : 4.72
Consensus Log Po/w : 4.27

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.33
Solubility : 0.00999 mg/ml ; 0.0000466 mol/l
Class : Moderately soluble
Log S (Ali) : -3.85
Solubility : 0.0304 mg/ml ; 0.000142 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.56
Solubility : 0.000587 mg/ml ; 0.00000274 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.26

Safety of [ 5216-31-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5216-31-9 ]

* 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 [ 5216-31-9 ]

[ 5216-31-9 ] Synthesis Path-Downstream   1~82

  • 1
  • [ 6214-23-9 ]
  • [ 5216-31-9 ]
  • methyl [2,3,4,5-tetra(4'-fluorophenyl)cyclopenta-2,4-dienylidene]acetate [ No CAS ]
  • 2
  • [ 352-34-1 ]
  • [ 1066-54-2 ]
  • [ 5216-31-9 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20℃; for 18h;Inert atmosphere; Schlenk technique; Darkness; General procedure: PdCl2(PPh3)2 (168mg, 0.24 mmol, 6.0 mol%), CuI (76 mg, 0.40 mmol, 10 mol%) and 1-bromo-4-iodobenzene (1.1 g, 4.0 mmol) were added into a 50-mL 2-neck round-bottom flaskwith a magnetic stirring bar. The flask was evacuated and refilled with N2 gasfollowing the usual Schlenk technique. Dry toluene (20 mL) was added while stirring.N2-sparged DBU (3.6 mL, 24 mmol, 6.0 equiv), trimethylsilylacetylene (0.28 mL, 2.0mmol, 1.0 equiv) and distilled water (29 muL, 1.6 mmol, 40 mol%) were addedconsecutively. The reaction flask was wrapped with aluminum foil and stirred at roomtemperature for 18 h. The reaction was quenched with water (20 mL) and extractedwith diethyl ether (20 mL). The organic layer was washed with 10% aqueous HCl (3 15 mL), brine (20 mL), dried over Na2SO4, gravity-filtered and the solvent removedin vacuo. The crude product was purified by silica gel column chromatography inhexane and concentrated in vacuo to obtain 1b in 34% (229 mg, 0.68 mmol) yield aswhite crystals.1
  • 4
  • [ 26305-75-9 ]
  • [ 5216-31-9 ]
  • sodium cyclopentadienide [ No CAS ]
  • [ 616-38-6 ]
  • [ 1092707-47-5 ]
  • (η5-carbomethoxycyclopentadienyl)(triphenylphosphine)-2,3,4,5-tetra(para-fluorophenyl)cobaltacyclopentadiene [ No CAS ]
  • 5
  • [ 26305-75-9 ]
  • [ 5216-31-9 ]
  • sodium cyclopentadienide [ No CAS ]
  • (η4-tetra(para-fluorophenyl)cyclobutadiene)(η5-cyclopentadienyl)cobalt [ No CAS ]
  • [ 1092707-34-0 ]
  • 6
  • [ 5216-31-9 ]
  • [ 588-56-7 ]
YieldReaction ConditionsOperation in experiment
83% With pyridine; hydrogen; at 80℃; under 22502.3 Torr; for 16h;Autoclave; The added AuNPore (5.0mg, 5mol%)In the autoclave of the catalyst,Pyridine (3 mL) was added,Substrate 1,2-bis (4-fluorophenyl) acetylene (107.12 mg, 0.5 mmol)Hydrogen (3.0 MPa),Placed in a magnetic stirrer at 80 C for 16 h,Column chromatography (silica gel,200-300 mesh; development agent,Petroleum ether) to give 89.0 mg of (Z) -1,2-bis (4-fluorophenyl)Yield 83%.
52% With borane-ammonia complex; cobalt(II)(2,6-bis(morpholinomethyl)pyridine)bromide; In methanol; at 50℃; for 14h;Inert atmosphere; General procedure: To an oven-dried 10 mL screw-capped vial, alkyne 1 (0.5 mmol), amino-borane (0.6 mmol), Co-complex (2-4 mol%) and methanol (1 mL) were added under a gentle stream of argon.The mixture was stirred for 10-14 h at 50-80 C (bath temperature) followed by cooling to 25C. The mixture was filtered through a celite pad with several washings (3 x 3 mL dichloromethane) and concentrated in vacuo. The yield of alkene was determined by GC with diphenyl as the internal standard.
With [(PPh3)CuCl]4; hydrogen; lithium tert-butoxide; In isopropyl alcohol; toluene; at 100℃; under 3800.26 Torr; for 3h;Schlenk technique; Autoclave; General procedure: In a glove box, to a vial, [(PPh3)CuCl]4 (7.2 mg, 5.0 mumol),toluene (1.0 mL), LiOtBu (40 mg, 0.50 mmol) and iPrOH (60 mg, 1.0 mmol) were added in thisorder. After the resulting mixture was stirred for 1 min at room temperature, 1a (160 mg, 1.0 mmol)and toluene (2.0 mL) were added. The vial was placed in an autoclave and the autoclave was takenout of the glove box. N2 in the autoclave was replaced with H2 by positive pressure of H2. Then, themixture was stirred at 100 C for 3 h under 5 atm of H2. After cooling to room temperature, H2 wasreleased and the mixture was diluted with EtOAc. The conversion was determined by GC analysiswith n-tridecane (18 mg, 0.10 mmol) as an internal standard. The resulting solution was filteredthrough a pad of silica gel and the yields of the products were determined by 1H NMR analysis with1,3,5-trimethoxybenzene as an internal standard.
  • 7
  • [ 5216-31-9 ]
  • [ 244090-34-4 ]
  • [ 1185863-96-0 ]
  • 8
  • [ 352-34-1 ]
  • [ 471-25-0 ]
  • [ 55606-94-5 ]
  • [ 5216-31-9 ]
YieldReaction ConditionsOperation in experiment
68%; 8%Chromat. With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane; In dimethyl sulfoxide; at 30 - 80℃; for 9h;Darkness; Aerobic condition; General procedure: Aryl iodide (2.0 mmol), propiolic acid (168.1 mg, 2.4 mmol) Pd(PPh3)2Cl2 (70.2 mg, 0.1 mmol), 1,4-bis(diphenylphosphino)butane (85.3 mg, 0.2 mmol), CuI (38.1 mg, 0.2 mmol), DBU (730.8 mg, 4.8 mmol) and K2CO3 (331.7 mg, 2.4 mmol) were combined with DMSO (4.0 mL) in a small round-bottomed flask. The resulting reaction mixture was stirred under aerobic and dark conditions at 30 C for 6 h and subsequently at 80 C for 3 h. The solvent was removed from the reaction mixture under the vacuum. The crude mixture was dissolved with Et2O (15 mL), washed with brine (15 mL × 3), dried over MgSO4, and filtered. The combined solvent was removed under vacuum, and the resulting crude product was purified by flash chromatography on silica gel.
  • 9
  • [ 2789-88-0 ]
  • [ 5216-31-9 ]
  • [ 1611-83-2 ]
  • [ 1309763-17-4 ]
  • [ 1309763-16-3 ]
  • 10
  • [ 5216-31-9 ]
  • [ 1611-83-2 ]
  • [ 1309763-16-3 ]
  • 11
  • [ 88070-48-8 ]
  • [ 5216-31-9 ]
  • 3,4-bis(4-fluorophenyl)-2-methylisoquinolin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium iodide dihydrate; palladium 10% on activated carbon; potassium acetate; caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 36h;Schlenk technique; General procedure: A mixture of a substituted benzamide (1) (0.3 mmol, 1.0 equiv),an alkyne (2) (0.6 mmol or 0.9 mmol, 2.0 equiv or 3.0 equiv),10% Pd/C (0.03 mmol, 10 mol%, Alfa Aesar, No. 044696, eggshell,reduced), NaI·2H2O (0.6 mmol, 2.0 equiv), Cs2CO3 (0.3 mmol, 1.0equiv), and KOAc (0.6 mmol, 2.0 equiv) was weighted in a Schlenktube equipped with a stir bar. DMF (1.0 mL) was added and themixture was stirred at 120 C for 36 h under air. Afterwards, themixture was filtered and washed with H2O (30 mL) and extractedwith CH2Cl2 (3×30 mL). The combined organic phase was driedwith anhydrous Na2SO4. After removal of solvents under reducedpressure, the residue was absorbed to small amounts of silica. Thepurification was performed by flash column chromatography onsilica gel with EA:PE (Petroleum ether) = 1:5 or 1:10 as eluent.
  • 12
  • [ 2446-51-7 ]
  • [ 5216-31-9 ]
  • [ 1346684-69-2 ]
YieldReaction ConditionsOperation in experiment
94% With di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; anhydrous Sodium acetate In methanol at 20℃; for 8h; Inert atmosphere;
84% With bis[dibromido(η6-p-cymene)osmium(II)]; anhydrous Sodium acetate; glacial acetic acid at 60℃; for 24h;
82% With di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; potassium 2,4,6-trimethylbenzoate In lithium hydroxide monohydrate at 60℃; for 12h; Schlenk technique; Inert atmosphere; 2.2 General Procedure for Ruthenium-CatalyzedAnnulation of N-Methoxybenzamideswith Alkynes in PEG-400/H2O General procedure: A Schlenk tube equipped with a magnetic stir bar was charged with [RuCl2(p-cymene)]2 (9.2 mg, 0.015 mmol,3 mol%), N-methoxybenzamide 1 (0.5 mmol), potassium 2,4,6-trimethylbenzoate (20.3 mg, 0.1 mmol, 20 mol%), and PEG-400 (2.0 mL). The reaction tube was evacuated and backfilled with argon (this sequence was carried out three times) and then alkyne 2 (0.75 mmol, if liquid) and water(1.0 mL) were added by syringe (alkyne that was solid at room temperature was added with the ruthenium catalyst).The reaction mixture was stirred at 60 °C for 12 h underan argon atmosphere. After being cooled to room temperature,the reaction mixture was extracted with diethyl ether(3 × 10 mL). The combined ether layer was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired isoquinolone 3.
50% With di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; potassium 2,4,6-trimethylbenzoate In lithium hydroxide monohydrate at 60℃; for 16h; Inert atmosphere;
With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; caesium acetate In chlorobenzene at 60℃; for 16h; Schlenk technique;
With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; caesium acetate In methanol at 60℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;

  • 13
  • [ 5216-31-9 ]
  • [ 62-53-3 ]
  • [ 628320-79-6 ]
YieldReaction ConditionsOperation in experiment
76% With Cp*Rh(H2O)3(OTf)2; oxygen; acetic anhydride; In pentan-1-ol; at 100℃; for 24h; The aniline to 1a (55. 0muL, 0 . 6mmol), <strong>[5216-31-9]1,2-bis(4-fluorophenyl) acetylene</strong> 2d (85.7 mg, 0 . 4mmol), Cp*Rh (H2O)3(OTf)2(11.8 mg, 5mol %), acetic anhydride (59. 0muL, 0 . 6mmol), adding 2.0 ml in tertiary amyl alcohol , oxygen (1atm), 100 degrees reaction 24 hours after stop the reaction, add NaOH (48 mg, 1 . 2mmol) and methanol 2 ml after stirring one hour, column chromatography get the pure product 2,3-di(4-fluorophenyl)-indole 3ad. The product is white solid, yield 76%.
  • 14
  • [ 613-91-2 ]
  • [ 5216-31-9 ]
  • [ 1401548-50-2 ]
YieldReaction ConditionsOperation in experiment
44% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper(II) acetate monohydrate; Trimethylacetic acid; In methanol; at 120℃; for 24h;Sealed tube; General procedure: A mixture of acetophenone oxime 1a (0.2 mmol), diphenylacetylene 2 (0.24 mmol, 1.2 equiv), [Cp*IrCl2]2 (3 mol%), PivOH (0.06 mmol, 0.3 equiv), Cu(OAc)2. H2O (0.4 mmol, 2 equiv) and MeOH (2 mL) in a 15mL glass vial [sealed with poly(tetrafluoroethylene)(PTFE) cap] was heated at 120 C with vigorous stirring for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through Celite. The filtrate was concentrated in vacuo and purified by column chromatography on silica gel to give the corresponding product 4.
  • 15
  • [ 5216-31-9 ]
  • [ 100-52-7 ]
  • [ 1264166-21-3 ]
YieldReaction ConditionsOperation in experiment
59% With tert.-butylhydroperoxide; ferrocene; In acetonitrile; at 80 - 140℃; 0.2 mmol of benzaldehyde, 0.3 mmol of bis-(4-fluorophenyl)acetylene, 0.001 mmol of ferrocene, 0.6 mmol of t-butyl hydroperoxide, and 2.0 mL of acetonitrile were added to a 10 mL reaction tube at 80-140 C. In the oil bath, the reaction is 20-30h. The reaction was stopped and cooled to room temperature. The reaction solution was diluted with dichloromethane and extracted three times with water. The organic phase was dried over anhydrous Na 2 SO 4 and filtered. Column chromatography gave 36.9 mg of the desired product in a yield of 59%.
  • 16
  • [ 766-98-3 ]
  • [ 352-34-1 ]
  • [ 5216-31-9 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃;Schlenk technique; Inert atmosphere; General procedure: Chapter one: A 100 mL schlenk tube was charged with iodobenzene (3.0 mmol), ethynyltrimethylsilane (3.6 mmol), PdCl2(PPh3)2 (0.15 mmol), CuI (0.15 mmol), Et3N:THF = 3:2 (10.0 mL). Then the tube was charged with nitrogen, and was stirred at room temperature for the indicated time until complete consumption of starting material as monitored by TLC analysis. After the completion of the reaction, then the reaction mxtuire was filtered and the filtrate diluted in ethyl acetate and washed with water. The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The crude product was purified by silica gel column chromatography (petroleum ether unless otherwise noted) to give the corresponding trimethyl(phenylethynyl)silanes, and used for the next reaction.
  • 17
  • [ 1271-86-9 ]
  • [ 5216-31-9 ]
  • (Sp)-1-[(N,N-dimethylamino)methyl]-2-(6-fluoro-2,3,4-tris(4-fluorophenyl)naphthalen-1-yl)ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With t-Boc-L-valine; tetrabutylammomium bromide; oxygen; palladium diacetate; potassium carbonate; In N,N-dimethyl acetamide; at 80℃; for 48h; General procedure: To a solution of alkyne 2 (0.46 mmol) in DMA (1.5 mL) wasadded Boc-L-Val-OH (8.7 mg, 0.04 mmol), Pd(OAc)2 (4.5 mg,0.02 mmol), K2CO3 (27.6 mg, 0.2 mmol), TBAB (tetrabutylammonium bromide) (16.1 mg, 0.05 mmol) and ferrocene 1(0.02 mmol) successively. The mixture was stirred at 80 C under air (open flask) for 48 h. After the reaction was complete,it was quenched with saturated aqueous NaHCO3 solution and extracted with EtOAc for three times. The combined organic layers were washed with H2O and brine successively, then driedover anhydrous Na2SO4 and filtrated. After the solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether 1:10, v/v, 3% Et3N) to afford the desired product 3.
  • 18
  • [ 169057-08-3 ]
  • [ 5216-31-9 ]
  • C27H19F2NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With copper diacetate; palladium diacetate; In N,N-dimethyl acetamide; dimethyl sulfoxide; tert-butyl alcohol; at 100℃; for 12h;Inert atmosphere; Sealed tube; General procedure: To a mixed solvent of t-BuOH/DMAc/DMSO (0.6 mL/0.3 mL/0.1mL) containing Pd(OAc)2 (10 mol %) and Cu(OAc)2 (0.3 mmol,2 equiv.), substrate 1 (0.15 mmol, 1.0equiv.) and 2 (0.23 mmol, 1.5 equiv.)were added under nitrogen atmosphere. The mixture was stirred at 100 C until 1 disappeared as monitored by TLC. Oncooling, the solvent was removed under reduced pressure and the residue waspurified by flash chromatography (petroleum ether: ethyl acetate = 12:1 to 10:1)to give the product 4
  • 19
  • [ 5216-31-9 ]
  • [ 7606-13-5 ]
  • [ 1609562-74-4 ]
YieldReaction ConditionsOperation in experiment
87% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In 1,2-dichloro-ethane; at 120℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: N,N-Diethylpicolinamide (1; 0.2 mmol, 1.0 equiv), [Cp*RhCl2]2 (0.005 mmol, 2.5 mol%), AgSbF6 (0.02 mmol, 10 mol%), Cu(OAc)2 (0.4 mmol, 2.0 equiv), alkyne 2 (0.44 mmol, 2.2 equiv) and DCE (2 mL) were added to a 20-mL Schlenk tube. After being purged with nitrogen, the mixture was stirred at 120 C for 24 h. Then concd aq NH3 (2 mL) was added and stirred for 5 min. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on silica gel to afford isoquinoline 3.
  • 20
  • [ 5216-31-9 ]
  • [ 591-51-5 ]
  • [ 1223047-89-9 ]
YieldReaction ConditionsOperation in experiment
59% General procedure: To a solution of Cp2ZrCl2 (1.2 mmol, 351 mg) in 5 mL THF, n-BuLi (2.4 mmol, 1.5 mL, 1.6 M in hexane) was added at-78 C and the mixture was stirred for 1 h at the same temperature. To this solution, 4-dimethylaminopyridine (DMAP, 122 mg, 1.0 mmol) was added. The resulting mixture was warmed to room temperature and stirred for 1 h. Diphenylacetylene (1.0 mmol, 178 mg) was added and the mixture was stirred for 1 h at the same temperature. Subsequently, PhLi (2.0 mmol) was added and the solution was stirred for 12 h at room temperature. Then TCQ (2.0 mmol) was added and stirred for another 12 h to afford alkenylzirconocene 4a. The mixture was quenched with HCl solution to afford product 3a in 62% isolated yield.
  • 21
  • [ 5216-31-9 ]
  • [ 673485-54-6 ]
  • [ 1610537-53-5 ]
YieldReaction ConditionsOperation in experiment
85% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; acetic acid at 120℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;
  • 22
  • [ 5216-31-9 ]
  • [ 1571899-52-9 ]
  • [ 1609205-86-8 ]
YieldReaction ConditionsOperation in experiment
61% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; In acetonitrile; at 100℃; for 20h;Sealed tube; General procedure: To an oven-dried sealed tube charged with N-p-tolyl-1H-indole-1-carboxamide (1a) (37.5 mg, 0.15 mmol, 100 mol%), [RhCp*Cl2]2(2.3 mg, 0.0037 mmol, 2.5 mol %), and Cu(OAc)2.H2O(60 mg, 0.3 mmol, 200 mol %) was added 4-octyne (2a) (33 mg, 0.3 mmol, 200 mol %) and MeCN(1 mL). The reaction mixture was allowed to stir for 20 h at 100 oC.The reaction mixture was diluted with EtOAc (10 mL) and concentrated in vacuo. The residue was purified by flash column chromatography (n-hexanes/EtOAc= 100:1) to afford the alkenylated product 3a (25.2 mg) in 74% yield.
  • 23
  • [ 5216-31-9 ]
  • [ 217813-03-1 ]
  • [ 1450812-34-6 ]
YieldReaction ConditionsOperation in experiment
59% With bis(eta3-allyl-mu-chloropalladium(II)); tri-tert-butyl phosphine; tetramethylammonium bromide; lithium ethoxide; In toluene; at 120℃; for 24h;Inert atmosphere; Under a nitrogen atmosphere, 1 mmol of 2- (trimethylsilyl) -3-methoxyphenyl trifluoromethanesulfonate, 2 mmol of bis (4-fluorophenyl) acetylene, 0.025 mmol Of chlorinated allyl palladium dimer, 0.1 mmol of tri-t-butylphosphine, 2 mmol of lithium ethoxide, 1.5 mmol of tetramethylammonium bromide and 5 mL of toluene solvent.The reaction temperature was constant at 120 C for 24 hours using an oil bath.After cooling, the filtrate was concentrated and the filtrate was concentrated to give the crude product.The crude product was subjected to decolorization by silica gel column eluting with petroleum ether to give 223 mg of 1,1-dimethyl-3,4-bis (4-fluorophenyl) -7-methoxybenzothiazole > 98%, white solid), the separation yield was 59%.
  • 24
  • [ 5216-31-9 ]
  • [ 172487-18-2 ]
  • 1-ethoxy-2,3-bis(4-fluorophenyl)phosphindole 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With silver(I) acetate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere; General procedure: A suspension of phosphinate 1a (85 mg, 0.50 mmol), diphenylacetylene(2a; 178 mg, 1.00 mmol), AgOAc (167.0 mg, 1.00 mmol) inDMSO (2.0 mL) was stirred under N2 atmosphere at r.t., and then at 120 C for 12 h. At r.t., the reaction mixture was diluted with H2O(10 mL) and extracted with EtOAc (3 ~ 25 mL). The combined organiclayers were dried (Na2SO4). After filtration and evaporationof the solvents in vacuo, the crude product was purified by columnchromatography on silica gel (n-hexane.EtOAc, 5:1 2:1) to afford3aa as an off-white oil; yield: 104 mg (60%).
  • 25
  • [ 5378-52-9 ]
  • [ 5216-31-9 ]
  • 3,4-bis(4-fluorophenyl)-2-aminoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate; copper(II) acetate monohydrate; In N,N-dimethyl-formamide; at 120℃; for 6.0h;Sealed tube; Inert atmosphere; Green chemistry; 1032 g were weighed in this order1,2-bis (4-methylphenyl) acetylene (0.5 mmol),0.2191 g of <strong>[5378-52-9]phenyl-1H-tetrazole</strong> (1.5 mmol),0 ? 0031 g [Cp * RhCl2] 2 (0. 005 mmol),0 ? 1997g Cu (OAc) 2 .H20 (1.0mmol) and0,0984 g of potassium acetate (1.O mmol) was addedIn a 25 mL sealed tube containing a magnetic stir bar,2. OmL N, N-diethylformamide was added.The cannula was sealed under nitrogen,The mixture was stirred in an oil bath at 120 C for 6 hours.After the end of the reaction, the column was separated with petroleum ether-ethyl acetate as the eluent,Obtained as a white solid, 0.1054 g,Target productThe isolated yield of 3,4-bis (4-methylphenyl) -2-aminoisoquinoline was 65%.
  • 26
  • [ 5216-31-9 ]
  • [ 114-83-0 ]
  • N-(2,3-bis(4-fluorophenyl)-1H-indol-1-yl)acetamide [ No CAS ]
  • 27
  • [ 5216-31-9 ]
  • 3-bromo-6-fluoro-2-(4-fluorophenyl)benzo[b]selenophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With selenium(IV) oxide; hydrogen bromide; triethylamine; cyclohexene; In 1,4-dioxane; at 20℃; for 72h; General procedure: Selenium(IV) oxide (9.32 g, 84.0 mmol) was dissolved in 48% hydrobromic acid (36.0 ml) and stirred at room temperature for15 min. A solution of 1 (5.00 g, 21.0 mmol), cyclohexene (5.18 g, 63.0 mmol), and triethylamine (11.7 ml, 84.0 mmol) in dioxane (100 ml) was added dropwise, and the reaction mixturewas stirred for 24 h. Then reaction mixture was quenched with EtOAc (ethyl acetate) (400 ml) and brine (100 ml). After stirring for additional 15 min, organic phase was separated and aqueous phase was extracted with EtOAc (2 200 ml). Combined organic phases were washed with brine (100 ml), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a mixture of petroleum ether and EtOAc (40:1) as eluent. Note: not collectable solid precipitates appear in first fractions. After evaporation of solvents, pale yellow oil was obtained, which slowly crystallizes upon standing at room temperature. After recrystallization from a mixture of petroleum ether and EtOAc (5:1), compound 2 was obtained in 50% yield (4.16 g) as a white crystalline solid;
  • 28
  • [ 5216-31-9 ]
  • [ 1137-96-8 ]
  • 2-(phenyl)-3-(4-fluorophenyl)-3-(4-fluorobenzoyl)-2,3-dihydro-1H-indole [ No CAS ]
  • 2-(phenyl)-3-(4-fluorophenyl)-3-(4-fluorobenzoyl)-2,3-dihydro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid; In ethyl acetate; at 80℃; for 15h;Sealed tube; Inert atmosphere; General procedure: Nitrones (0.2 mmol), diarylacetylenes (0.3 mmol), [Cp*RhCl2]2 (4 mol%), AgSbF6 (16 mol%), PivOH (2.0 equiv)and ethyl acetate (2 mL) were charged into the sealed tube. The reaction mixture was stirred at 80 C for 15 h. After cooled to room temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using triethylamine/PE or PE/EA to afford compounds 3.
  • 29
  • [ 5216-31-9 ]
  • [ 62-53-3 ]
  • [ 366-63-2 ]
YieldReaction ConditionsOperation in experiment
72% With 1,10-Phenanthroline; copper(II) choride dihydrate; silver trifluoromethanesulfonate; 1,2-bis-(diphenylphosphino)ethane; palladium dichloride; In 1,4-dioxane; water; at 100℃; for 24h; General procedure: To a tube equipped with a condenser was added aniline (1, 0.2 mmol), diphenylacetylene (2, 0.4 mmol), PdCl2 (3.5 mg,0.02 mmol), CuCl2·2H2O (6.8 mg, 0.04 mmol), DPPE (7.9 mg,0.02 mmol), 1,10-phenanthroline monohydrate (15.9 mg, 0.08 mmol), AgOTf (10.3mg, 0.04 mmol), H2O (18 mg, 18 muL, 1 mmol), dioxane (0.25 mL). Themixture was stirred and heated at 100 C for 24 h until the substratedisappeared as monitored by TLC. The reaction mixture was cooled down to room temperature,dried under vacuum and purified by column chromatography on silica gel toobtain the desired products 3 (petroleumether:ethyl acetate = 20:1).
  • 30
  • [ 42918-20-7 ]
  • [ 5216-31-9 ]
  • 1,2-bis(4-fluorophenyl)-3-methylnaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With palladium(II) trifluoroacetate; caesium carbonate; glyoxal bis(N-methyl-N-phenylhydrazone) In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;
  • 31
  • [ 5216-31-9 ]
  • [ 611-73-4 ]
  • C22H14F2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With boron trifluoride diethyl etherate; In fluorobenzene; at 70℃; for 5h; In a reaction tube 0. 3 mmol of benzoylformic acid,0. 6 mmol of bis (4-fluorophenyl) acetylene,0. 09 mmol of boron trifluoride etherate and 2 mL of fluorobenzene at 70 C for 5 h. After completion of the reaction, the solvent was distilled off under reduced pressure, and the mixture was further subjected to column chromatography using a mixture of petroleum ether and ethyl acetate. The volume ratio of ethyl acetate was 5: 1, then the pure product was obtained in a yield of 91% and a purity of 98%.
  • 32
  • [ 5216-31-9 ]
  • [ 101-42-8 ]
  • 2,3-bis(4-fluorophenyl)-N,N-dimethyl-1H-indole-1-carboxamide [ No CAS ]
  • 33
  • [ 13909-34-7 ]
  • [ 5216-31-9 ]
  • [ 1864-94-4 ]
  • C28H19F2NO3S [ No CAS ]
  • 34
  • [ 5216-31-9 ]
  • [ 21399-33-7 ]
  • [ 1613470-78-2 ]
YieldReaction ConditionsOperation in experiment
69% With Cp*Rh(H2O)3(OTf)2; benzoic acid; In methanol; at 25℃; for 24h; The phenylhydrazone 4b (0.3mmol), <strong>[5216-31-9]1,2-bis(4-fluorophenyl) acetylene</strong> 2d(0.5mmol), Cp*Rh (H2O)3(OTf)2(0.01mmol), benzoic acid (0.125mmol), by adding 4.0 ml methanol, the air lower, 25oC reaction 24 hours after cessation of the reaction, pure product of column chromatography to obtain isoquinoline 4bd. The product is white solid, yield 69%.
  • 35
  • [ 5216-31-9 ]
  • [ 34801-22-4 ]
  • C40H24F2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With silver hexafluoroantimonate; [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; copper(II) acetate monohydrate; In tetrahydrofuran; at 120℃; for 12h;Schlenk technique; Inert atmosphere; General procedure: A 25 mL Schlenk-type tube (with a Teflon high pressure valve and side arm) was charged withcompound 1a (34.6 mg, 0.10 mmol), alkynes (0.20 mmol), Cu(OAc)2.H2O (5.0 mg, 0.025 mmol),[RuCl2(p-cymene)]2 (6.1 mg, 0.01 mmol), AgSbF6 (13.7 mg, 0.04 mmol) and THF (1 mL). Thereaction tube was evacuated and back-filled with N2 (3 times, ballon). After the reaction mixturewas stirred at 120 oC for 12 h, it was allowed to cool down to room temperature. The reactionmixture was diluted with ethyl acetate (20 mL), and then filtered through a pad of Celite. Thefiltrate was washed with brine (10 mL), dried over Na2SO4, and concentrated in vacuo. Theresidue was purified by silica gel preparative TLC to give the corresponding products
  • 36
  • [ 38707-70-9 ]
  • [ 5216-31-9 ]
  • C38H23F4NO [ No CAS ]
  • 37
  • [ 38707-70-9 ]
  • [ 5216-31-9 ]
  • C38H22BrF4NO [ No CAS ]
  • 38
  • [ 5216-31-9 ]
  • [ 100-09-4 ]
  • [ 1223047-72-0 ]
YieldReaction ConditionsOperation in experiment
71% With [bis(acetato)-(eta-p-cymene)-ruthenium]; In 1,4-dioxane; n-heptane; 1,3,5-trimethyl-benzene; at 80℃; for 24h;Inert atmosphere; Sealed tube; General procedure: The general procedure for decarboxylative alkyne hydroarylation is as follows. In a nitrogen-atmosphere glovebox, [Ru(p-cymene)(OAc)2] (7, 71 mg, 0.2 mmol) and 10.0 ml of mixed solvent (4.0 ml dioxane, 4.0 ml mesitylene and 2.0 ml heptanes) were added into a 20 ml scintillation vial equipped with a magnetic stir bar. The mixture was stirred for ten minutes to be used as a homogeneous stock solution of catalyst precursor. A 4 ml scintillation vial equipped with a magnetic stir bar was charged with the alkyne substrate (0.2 mmol, 1.0 equiv.), arenecarboxylic acid substrate (0.4 mmol) and 1.0 ml of the stock solution of catalyst precursor (containing 0.02 mmol of complex 7). The vial was then sealed with a Teflon-lined cap, transferred out of the glovebox and stirred in an 80 C oil bath for 24 hours. The reaction mixture was cooled to room temperature and then all volatile materials were removed under reduced pressure. Further purification was achieved by flash column chromatography using dichloromethane, ethyl acetate and hexanes as the eluent. The E/Z alkene stereo- and regioselectivity for aromatic substitution was determined by 1 H NMR spectroscopy of the unpurified reaction mixture. Yields of the isolated products are based on the average of two runs under identical conditions.
  • 39
  • [ 934-37-2 ]
  • [ 5216-31-9 ]
  • 3,4-bis(4-flurophenyl)-2-methylimidazo[5,1,2-cd]indolizine [ No CAS ]
  • 40
  • [ 5216-31-9 ]
  • [ 406207-65-6 ]
  • 2-tert-butyl-3,4-bis(4-fluorophenyl)imidazo[5,1,2-cd]indolizine [ No CAS ]
  • 41
  • [ 5216-31-9 ]
  • C15H17NO4 [ No CAS ]
  • C29H23F2NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With benzoic acid; palladium dichloride; In N,N-dimethyl acetamide; at 120℃; under 760.051 Torr; for 24h; Take 2-carbonyl butyryl-7- carbonylmethyl ester - indolizine55.1 mg (equivalent to 0.20 mmol)1,2-bis (4-fluorophenyl) acetylene was 64.3 mg (corresponding to 0.30 mmol)Palladium chloride was 3.5 mg (equivalent to 0.02 mmol)(Corresponding to 0.03 mmol) of 2,6-dichlorobenzoic acid and 2.0 ml of N, N-dimethylacetamide were heated and stirred at 120 C for 24 hours under 1 atmosphere of oxygen to obtain a fifth numbered target product 76.0 mg (78% yield).
  • 42
  • [ 1008-89-5 ]
  • [(eta.(5)-pentamethylcyclopentadienyl)Rh(H2O)3](OTf)2 [ No CAS ]
  • [ 1493-13-6 ]
  • [ 5216-31-9 ]
  • [ 1440420-79-0 ]
YieldReaction ConditionsOperation in experiment
90% With oxygen; In methanol; at 120℃; under 760.051 Torr; for 22h; The 2 - phenylpyridyl 1a (71 muL, 0 . 5mmol), two 1, 2 - (4 - fluorophenyl) acetylene 2d (107.1 mg, 0.5 mmol), Cp * Rh (H2 O)3 (OTf)2 (3.0 mg, 1 mol %), HOTf (44 muL, 0.5 mmol), adding 2.0 ml in methanol, oxygen (1atm), 120 o C reaction 22 hours after stopping the reaction, diatomaceous earth filter, dichloromethane washing, to collect organic phase of the drying solvent, methanol/ethyl ether/petroleum ether (1:4: 100) washing, to get the pure product isoquinoline salt derivative 3ad. The product is a white solid, yield 90%
  • 43
  • [ 5216-31-9 ]
  • [ 4403-69-4 ]
  • 2,3-bis(4-fluorophenyl)-5-hydro-1,4-benzodiazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% To the reaction tube, adding 10.1 mg of iodine, 42.8 mg of <strong>[5216-31-9]1,2-bis(4-fluorophenyl)acetylene</strong>, 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, finally, 51.2 mg of compound 7 was obtained by conventional treatment, and the yield was 77%.
77% To the reaction tube, 10.1 mg of iodine was added, and 42.8 mg1,2-bis (4-fluorophenyl) acetylene, 2 mL of dimethylsulfoxide, reacted in an oil bath at 130 C for 24 hours, the reaction solution was cooled to room temperature, and then 97.7 mg of 2-aminobenzylamine and1 mL of acetic acid and reacted in an oil bath at 100 C for 20 hours and finally by conventional treatment to give 51.2 mg of compound 6 in yield77%.
  • 44
  • [ 5216-31-9 ]
  • [ 122-79-2 ]
  • 3,4-bis(4-fluorophenyl)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.3% With copper acetylacetonate; tris(triphenylphosphine)ruthenium(II) chloride; di-n-butyliodotin hydride; 3-ethyl-1-methyl-1H-imidazol-3-ium 2,2,2-trifluoroacetate; In 1,4-dioxane; dimethyl sulfoxide; at 20 - 80℃; for 6h;Inert atmosphere; At room temperature, Under a nitrogen atmosphere, To a suitable amount of an organic solvent (a mixture of 1,4-dioxane and DMSO in a volume ratio of 1: 2.5) 100 mmol of the compound of formula (I) 170 mmol of the compound of formula (II), 11 mmol catalyst (2.75 mmol) Tris(triphenylphosphine)ruthenium(II) chloridewins and the f 8.25 mmol of a mixture of Bu2SnIH) 25 mmol accelerator Cu (acac) 2 and 12 mmol additives 1-ethyl-3-methylimidazole trifluoroacetate; then the temperature was raised to 80 C and the reaction was stirred at this temperature for 6 hours. After the reaction was completed, The reaction mixture was filtered while hot, The filtrate was naturally cooled to room temperature, Then add deionized water to fully oscillate, Then add chloroform extraction 2-3 times, combined with organic phase, Concentrated under reduced pressure, The resulting residue was subjected to flash column chromatography on silica gel, A mixed solvent of ethyl acetate and acetone in a volume ratio of 1: 2 was used as the eluent, To give the compound of formula (III) in a yield of 97.3%.
  • 45
  • [ 21251-12-7 ]
  • [ 5216-31-9 ]
  • [ 1346684-69-2 ]
YieldReaction ConditionsOperation in experiment
85.1% With bis(1,5-cyclooctadiene)nickel(0); sodium acetate; In methanol; at 80℃; for 8h; In the inductor is added in 20 ml of methanol, and sequentially adding 1 mmol of the formula (I - 3) compound, 1.2 mmol of the formula (II - 3) compound, 0.1 mmol cobalt acetylacetonate, 0.05 mmol double (1, 5 - cyclooctadiene) nickel and 0.5 mmol sodium acetate, heating to 80 C, reaction at the temperature for 8 hours. After the reaction is finished, remove the volatile matter, water and ethyl acetate extraction, the combined organic phase, salt water for washing and drying of sodium sulfate, then the solvent is removed. The resulting residue by 300 - 400 mesh silica gel column chromatographic separation, from the formula (III - 3) compound, yield of 85.1%
  • 46
  • [ 98-01-1 ]
  • [ 5216-31-9 ]
  • [ 7073-69-0 ]
  • [ 1264166-21-3 ]
YieldReaction ConditionsOperation in experiment
18% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; potassium iodide; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 20h;Inert atmosphere; General procedure: Using diaryl acetylenesA 5-mL two-necked flask equipped with a stir bar was charged with [RhCl(cod)]2 (0.0125 mmol,6.16 mg), BINAP (0.0125 mmol, 7.78 mg), 1a-c (0.25 mmol), KI (0.25 mmol, 41.5 mg), and Na2CO3(1.0 mmol, 106.0 mg). The central neck of the flask was equipped with a reflux condenser havinga N2 gas-bag (2 L), which was connected by a three-way stopcock at its top, and a rubber septumwas inserted i n to the side neck. The flask was evacuated and backfilled with N2 (three times).Xylene (1.0 mL), 2a (0.75 mmol, 161.3 mg), and furfural (1.75 mmol, 168.2 mg), were then added.After degassing the reaction mixture three times by the freeze-pump-thaw method, the flask wasfilled with N2. The mixture was placed in an oil bath that had been preheated to 140 C for 20 h.After cooling to room temperature, the resulting solution was filtered through a pad of celite, andthe filtrate was concentrated in vacuo. The resulting crude product was purified by flash columnchromatography on silica-gel to afford 3aa-3ac.
  • 47
  • [ 106-43-4 ]
  • [ 5216-31-9 ]
  • [ 73183-34-3 ]
  • (Z)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-tolyl-1,2-di(4-fluorophenyl)ethene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% General procedure: In a glove box, a vial was charged with 2 (0.75mmol) and a solution of Pd(OAc)2 (1.1 mg, 5.0 mumol) and RuPhos (4.7 mg, 10 mumol) in toluene(1.0 mL), and the resulting solution (solution A) was stirred for 10 min at room temperature. To another vial, CuCl (0.50 mg, 5.0 mumol), RuPhos (2.3 mg, 5.0 mumol), NaOtBu (96 mg, 1.0mmol), B2(pin)2 (254 mg, 1.0 mmol), toluene (1.0 mL), 1 (0.50 mmol) and the solution A were added in this order. The resulting mixture was stirred for 3 h at 80 C. After the reaction, the mixture was filtrated through a pad of silica gel and all of the volatiles were removed in vacuo.The product was purified by MPLC on silica gel to give the corresponding products.
  • 48
  • [ 318-54-7 ]
  • [ 5216-31-9 ]
  • 2,2,2-trifluoro-1-(6,7,8,9-tetrakis(4-fluorophenyl)-3-methyl-3H-benzo[e]indol-1-yl)ethanone [ No CAS ]
  • 49
  • [ 5216-31-9 ]
  • [ 20103-09-7 ]
  • C34H20F4N2 [ No CAS ]
  • 50
  • [ 5216-31-9 ]
  • [ 1293389-28-2 ]
  • C20H10F4N2S [ No CAS ]
  • (E,E)-4,7-bis[1,2-di(p-fluorophenyl)ethenyl]-5,6-difluoro-2,1,3-benzothiadiazole [ No CAS ]
  • 51
  • [ 5216-31-9 ]
  • [ 1293389-28-2 ]
  • (E,E)-4,7-bis[1,2-di(p-fluorophenyl)ethenyl]-5,6-difluoro-2,1,3-benzothiadiazole [ No CAS ]
  • (E,Z)-4,7-bis[1,2-di(p-fluorophenyl)ethenyl]-5,6-difluoro-2,1,3-benzothiadiazole [ No CAS ]
  • (Z,Z)-4,7-bis[1,2-di(p-fluorophenyl)ethenyl]-5,6-difluoro-2,1,3-benzothiadiazole [ No CAS ]
  • 52
  • [ 5216-31-9 ]
  • N‐(pyrimidin‐2‐yl)indoline [ No CAS ]
  • 6,7,8,9-tetrakis(4-fluorophenyl)-1-(2-pyrimidinyl)-2,3-dihydro-1H-benzo[g]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 12h;Schlenk technique; Inert atmosphere; 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.
  • 53
  • [ 5216-31-9 ]
  • [ 28144-70-9 ]
  • 2-(4-fluorophenyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With [2,2]bipyridinyl; palladium(II) trifluoroacetate; In 1,4-dioxane; at 100℃; for 0.12h; The starting material 2-aminobenzamide (0.3 mmol, 1 equiv),Starting material 4,4'-difluorodiphenylacetylene (0.9 mmol,3equiv), catalyst palladium trifluoroacetate (Pd(TFA) 2, 0.03 mmol, 10%) and ligand 2,2'-bipyridine (bpy, 0.06 mmol, 20%) were added to the reaction vessel for continuous reaction vessel Perform 3 pumping-oxygen operations and continueThe reaction solvent 1,4-dioxane (1,4-dioxane, 0.4 mL) was added to the reaction vessel, followed by reaction at 100 C in an oil bath.Stir at temperature until the end of the reaction (about 12h), then spin off the reaction solvent and pass column chromatography (filled with 300 mesh in column)400 mesh silica gel, separated by dichloromethane and ethyl acetate in a volume ratio of 10:1 as an eluent), after separation and purification, whiteSolid, yield 80%.
  • 54
  • [ 5216-31-9 ]
  • 6-fluoro-1-(4-fluorobenzyl)-3,4-bis(4-fluorophenyl)isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; hydroxylamine; potassium acetate; In ethanol; water; at 140℃; for 18h;Sealed tube; Inert atmosphere; 0.2142 g of bis(4-fluorophenyl)acetylene (1.0 mmol) was weighed in order.184 muL of 50% aqueous hydroxylamine solution (3.0 mmol),0.0062 g [Cp*RhCl2] 2 (0.01 mmol),0.0491 g of potassium acetate (0.5 mmol) in a 25 mL sealed tube containing a magnetic stir bar,Add 4.0 mL of ethanol.Seal the sealed tube under nitrogen conditions,It was stirred in an oil bath at 140 C for 18 hours.After the reaction, the column was separated with petroleum ether-ethyl acetate as an eluent.Obtained 0.1794g of a yellow solid.The isolated yield of the objective product 6-fluoro-1-(4-fluorobenzyl)-3,4-bis(4-fluorophenyl)isoquinoline was 81%.
  • 55
  • [ 5216-31-9 ]
  • [ 27257-15-4 ]
  • 5,6-bis(4-fluorophenyl)-7,12-dimethyl-7,12-dihydropyrido[2,3-b]pyrido[3',2':4,5]pyrrolo[2,3-e]indole [ No CAS ]
  • 56
  • [ 201230-82-2 ]
  • [ 2446-51-7 ]
  • [ 5216-31-9 ]
  • 9-fluoro-12-(4-fluorophenyl)isoindolo[2,1-b]isoquinoline-5,7-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% N-methoxybenzamide 1a was sequentially added to a 15 mL schlenk reaction tube as described in Example 1.(60.4 mg, 0.4 mmol), chlorobenzene (2 mL),2d (94.2mg, 0.44mmol), [Cp*RhCl2]2 (6.2mg, 2.5mol%), cesium acetate (23.0mg, 0.12mmol), heated in a 60 C oil bath for 16h, after the reaction is over, Palladium acetate (9.0 mg, 0.04 mmol), silver trifluoroacetate (176.7 mg, 0.8 mmol), sodium carbonate (21.2 mg, 0.2 mmol), vacuum three times, and then heated in a 120 C oil bath were added to the system. Stir for 15 h, quench the reaction with saturated ammonium chloride solution, extract with dichloromethaneThe organic phase was washed with deionized water and saturated brine and dried over anhydrous sodium sulfate. Filtration, concentration under reduced pressure, and separation and purification on silica gel column (eluent to a volume ratio of 10/1 in dichloromethane/ethyl acetate) afforded a yellow solid isoindole [2,1-b]isoquinolin-5. 7-diketone 3l (88 mg, 61%).
  • 57
  • [ 5216-31-9 ]
  • [ 42116-43-8 ]
  • 3-fluoro-5,6,13-tris(4-fluorophenyl)isoquinolino[2,1-b]cinnolin-7-ium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With silver hexafluoroantimonate; silver tetrafluoroborate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In acetonitrile at 80℃; Schlenk technique; Inert atmosphere; Sealed tube;
  • 58
  • diethyl(4-fluorophenyl)aluminum [ No CAS ]
  • [ 95895-33-3 ]
  • [ 5216-31-9 ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; at 60℃; for 34h;Inert atmosphere; General procedure: Under a dry nitrogen atmosphere, a mixture of Pd(PPh3)4 (5.78mg, 0.005mmol) and DPPE (3.98mg, 0.01mmol) in a reaction vessel was added an (hetero)arylaluminum compound (0.8mmol) in 2mL THF followed by an addition of alkynylbromides (0.50mmol). The resulted solution was stirred at 60C for 4-72h. After completion the reaction, the mixture was diluted with saturated ammonium chloride solution (5mL) and extracted with ethyl acetate (3×15mL). The combined organic layers were dried overanhydrous Na2SO4, filtered and evaporated in vacuum. The residue was subjected to flash column chromatography onsilica gel (hexane or ethyl acetate and hexane) to afford the corresponding 1, 2-disubstituted acetylenes 4
  • 59
  • [ 5216-31-9 ]
  • [ 102-04-5 ]
  • 3-benzyl-1,2-bis(4-fluorophenyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With [RhCl2(p-cymene)]2; potassium acetate; sodium carbonate; In toluene; at 100℃; for 24h;Inert atmosphere; Sealed tube; 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.
  • 60
  • [ 5216-31-9 ]
  • [ 1707-03-5 ]
  • 3,4-bis(4-fluorophenyl)-1-phenyl-1H-2,1-benzoxaphosphorin-1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; silver carbonate In 1,2-dichloro-ethane at 110℃; for 0.5h; Microwave irradiation; 14 Preparation method In a 10 mL microwave reaction tube, add compound I-1 (0.3 mmol), compound II-6 (0.36 mmol), Ag2CO3 (0.6 mmol), NaHCO3 (0.30 mmol), [RhCp*Cl2]2 (0.012 mmol) ), 1,2-dichloroethane (1.5 mL), the mixture was placed in a microwave reactor at 110° C. for 30 min at a microwave power of 100 w; TLC (thin layer chromatography) detected until the reaction was complete. Purification by post-treatment: cooling to room temperature, pressure concentration. The crude product was separated and purified by silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 15:12:1, and the pure product was obtained as a white solid, and the yield was 79%.
70% With chloropyridinecobaloxime(III); cesium fluoride; 9-(2-mesityl)-10-methylacridinium perchlorate In chloroform; water at 20℃; Inert atmosphere; Irradiation; Schlenk technique;
  • 61
  • [ 5216-31-9 ]
  • [ 51608-60-7 ]
  • (E)-N-(2,3-bis(4-fluorophenyl)-1-phenylallyl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium tert-butylate; In tetrahydrofuran; isopropyl alcohol; at 100℃; for 18h;Inert atmosphere; Green chemistry; 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, 1 g (42.8 mg, 0.2 mmol) and 2a (62 mg, 0.24 mmol) of raw materials were added.Stir at 100 C for 18 hours, cool to room temperature, and dilute with ethyl acetate.Filter through diatomaceous earth and concentrate to isolate the target product 4f after column chromatography.White solid, yield (73%).
  • 62
  • [ 2565-18-6 ]
  • [ 5216-31-9 ]
  • 2,6-dibutyl-3,4,7,8-tetrakis(4-fluorophenyl)-2,6-dihydro-2,6-naphthyridin-1,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With dirhodium tetraacetate; silver hexafluoroantimonate; silver carbonate; In tetrahydrofuran; at 20℃;Reflux; The preparation method is as follows: Add a solution of <strong>[2565-18-6]N-<strong>[2565-18-6]butyl acrylamide</strong></strong> in tetrahydrofuran at a concentration of 1 M in a clean 30 mL round bottom flask filled with stirring magnets. Then the catalyst cerium acetate (10 mol%), oxidant silver carbonate (3 eq), Additive silver hexafluoroantimonate (0.5 eq), 1,2-bis(4-fluorophenyl)acetylene (1.0 eq). This mixture was stirred at room temperature for one hour and then heated to reflux overnight. The reaction was detected by thin plate chromatography, and after cooling, the reaction was cooled to room temperature. The reaction was quenched with water and extracted 4×20 mL with ethyl acetate. Wash with saturated brine and dry over anhydrous sodium sulfate. The sodium sulfate was removed by filtration, and the solvent was evaporated to dryness. Using petroleum ether/ethyl acetate as the eluent, Purified by column chromatography (mobile phase: ethyl acetate/petroleum ether = 1/5) A pale yellow solid product was obtained in a yield of 66%.
  • 63
  • [ 1187-59-3 ]
  • [ 5216-31-9 ]
  • 3,4,7,8-tetrakis(4-fluorophenyl)-2,6-dimethyl-2,6-dihydro-2,6-naphthyridin-1,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With dirhodium tetraacetate; silver hexafluoroantimonate; silver carbonate; In toluene; at 20℃;Reflux; The preparation method comprises the following: A toluene solution of <strong>[1187-59-3]N-<strong>[1187-59-3]methyl acrylamide</strong></strong> was added to a clean 30 mL round bottom flask containing stirring magnets at a concentration of 1 M. Then the catalyst cerium acetate (10 mol%), oxidant silver carbonate (3 eq), Additive silver hexafluoroantimonate (0.5 eq), 1,2-bis(4-fluorophenyl)acetylene (1.0 eq). This mixture was stirred at room temperature for one hour and then heated to reflux overnight. The reaction was detected by thin plate chromatography, and after the reaction was completed, it was cooled to room temperature, and the reaction was quenched with water. Extract 4×20 mL with ethyl acetate and wash with saturated brine. Dry over anhydrous sodium sulfate and remove sodium sulfate by filtration. The solvent was evaporated under reduced pressure to give a crude material. Using petroleum ether/ethyl acetate as the eluent, Purified by column chromatography (mobile phase: ethyl acetate/petroleum ether = 1/2) A pale yellow solid product was obtained in a yield of 55%.
  • 64
  • [ 5216-31-9 ]
  • [ 1121545-24-1 ]
  • 7,8-bis(4-fluorophenyl)benzo[4,5]cyclohepta[1,2,3-de]naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With silver (II) carbonate; palladium diacetate; tri(4-chlorophenyl)phosphine In 1,2-dichloro-ethane at 80℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube;
  • 65
  • [ 5216-31-9 ]
  • C13H16IN3 [ No CAS ]
  • C27H23F2N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid; triethylamine; In N,N-dimethyl-formamide; at 110℃; for 24h;Inert atmosphere; 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 110C. 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.
  • 66
  • [ 5216-31-9 ]
  • [ 19099-54-8 ]
  • [ 73183-34-3 ]
  • (Z)-2-(5-fluoro-2-(2-(4-fluorophenyl)-1-(2-isopropylphenyl)vinyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With palladium diacetate; sodium carbonate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; 11 Preparation of (Z)-2-(5-fluoro-2-(2-(4-fluorophenyl)-1-(2-isopropylphenyl)vinyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 0.3 mmol of sodium carbonate, 0.1 mmol of 1,2-bis(4-fluorophenyl)acetylene, 0.005 mmol of palladium acetate, 0.005 mmol of bis(2-diphenylphosphinophenyl)ether, and 0.15 mmol of boronic acid pinacol ester. 0.15 mmol of 2-isopropyliodobenzene and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube, and the nitrogen was repeatedly filled 10 times, placed in an oil bath at 120 ° C for 24 hours; cooled to room temperature. The reaction solution was diluted with ethyl acetate and washed with water three times.Dry the organic phase with anhydrous Na2SO4, filter, concentrate, thin layer chromatographyPurification afforded 34.1 mg of the desired product in a yield of 71%. The nuclear magnetic and high resolution mass spectra of this compound were characterized as follows:
  • 67
  • [ 5216-31-9 ]
  • [ 15754-60-6 ]
  • (Z)-1-(4,5-bis(4-fluorophenyl)-2-methylpent-4-en-2-yl)-1H-pyrazole [ No CAS ]
  • 68
  • [ 5216-31-9 ]
  • [ 291514-02-8 ]
  • 4,5-bis(4-fluorophenyl)-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]isothiazole 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate; acetic acid In 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Schlenk technique; diastereoselective reaction;
  • 69
  • [ 5216-31-9 ]
  • [ 245368-50-7 ]
  • 5,6-bis(4-fluorophenyl)-1,3,4,4a,5,7a-hexahydrocyclopenta[c][1,2]thiazine 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate; trifluoroacetic acid In 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Schlenk technique; diastereoselective reaction;
  • 70
  • [ 5216-31-9 ]
  • [ 52260-22-7 ]
  • [ 1401548-50-2 ]
YieldReaction ConditionsOperation in experiment
98% With tris(acetonitrile)(eta5-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) delta 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) delta 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.
  • 71
  • [ 825644-26-6 ]
  • [ 5216-31-9 ]
  • (S)-6-fluoro-2,3-bis(4-fluorophenyl)-1H-inden-1-ol [ No CAS ]
  • C21H13F3O [ No CAS ]
  • 72
  • [ 5216-31-9 ]
  • [ 54015-96-2 ]
  • C39H24F4N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium acetate In 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; Inert atmosphere;
  • 73
  • [ 5216-31-9 ]
  • [ 136886-00-5 ]
  • C32H17F7NOP [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; silver carbonate; In 1,2-dichloro-ethane; at 130℃; for 0.333333h;Microwave irradiation; In a 10 mL microwave reaction tube, add compound I-1 (0.3 mmol), compound II-6 (0.36 mmol),Ag2CO3 (0.6mmol), NaHCO3 (0.36mmol),[RhCp*Cl2]2 (0.012mmol), 1,2-dichloroethane (3.0mL), the mixture was placed in a microwave reactor at 130 for 20min, TLC (thin layer chromatography) detected until the reaction was complete .Perform post-treatment purification: cool to room temperature and concentrate under pressure.The crude product is separated and purified by silica gel column chromatography[V (petroleum ether): V (ethyl acetate) = 7:1, that is, to obtain a pure product, white solid, yield: 87%.
  • 74
  • [ 591-50-4 ]
  • [ 5216-31-9 ]
  • [ 88-65-3 ]
  • 9,10-bis (4-fluorophenyl)phenanthrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetramethyl ammonium acetate; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h;Schlenk technique; Inert atmosphere; General procedure: To a Schlenk tube were added aryl iodides 1 (0.2 mmol, 1.0 equiv),1,2-diphenylethynes 2 (0.2 mmol, 1.0 equiv), 2-bromobenzoic acid 3 (0.24 mmol, 1.2equiv), PdCl2(dppf) (0.01 mmol, 5 mol %), K2CO3 (0.6 mmol, 3.0 equiv), Me4NOAc(0.6 mmol, 3.0 equiv), and DMSO (0.2 M, 1 mL). Then the tube was charged with nitrogen, and was stirred at 140 oC (oil bath temperature) for the indicated time until complete consumption of starting material as monitored by TLC analysis. After the reaction was finished, the resulting suspension was filtered and washed with ethyl acetate. The combined filtrates were concentrated under reduced pressure and purifiedon a silica-gel column chromatography (petroleum ether/EtOAc) to give product 4.
  • 75
  • [ CAS Unavailable ]
  • [ 5216-31-9 ]
  • [ 5472-23-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
67% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In tetrahydrofuran at 80℃; for 10h;
  • 76
  • [ 13129-23-2 ]
  • [ 5216-31-9 ]
  • C20H14F2O3 [ No CAS ]
  • C20H14F2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); 2,2-dimethylbutyric acid; tricyclohexylphosphine In 1,4-dioxane at 100℃; for 43h; Overall yield = 35 percent; regioselective reaction;
  • 77
  • [ 5216-31-9 ]
  • [ 19264-68-7 ]
  • [ 1264166-21-3 ]
  • [ 86-74-8 ]
YieldReaction ConditionsOperation in experiment
73% With silver hexafluoroantimonate; silver orthophosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 2,6-dimethylbenzoic acid In 1,2-dichloro-ethane at 120℃; for 24h; Inert atmosphere; Rh-Catalyzed Reaction of 9-Benzoylcarbazoles 1 with Alkynes 2. General procedure: To a 10 mL screw-cap vialwere added 9-benzoylcarbazole 1 (0.1 mmol), alkyne 2 (0.15 mmol) [Cp*RhCl2]2 (0.01 mmol, 6 mg),AgSbF6 (0.04 mmol, 14 mg), Ag3PO4 (0.01 mmol, 4 mg), 2,6-dimethylbenzoic acid (0.2 mmol, 30 mg),DCE (2 mL), and naphthalene (ca. 30 mg) as internal standard. The mixture was stirred under argon(1 atm) at 120 °C (bath temperature) for 24 h. The reaction mixture was diluted by ethyl acetate (40mL). The organic layer was washed by 1N HCl aq. (20 mL, three times) and brine (20 mL) and driedover Na2SO4. After evaporation of the solvents under vacuum, product 3 and 9H-carbazole 4 wereisolated by column chromatography on silica gel using hexane-ethyl acetate as eluent. Furtherpurification by GPC (gel permeation chromatography) was performed, if needed.
  • 78
  • [ 927384-42-7 ]
  • [ 5216-31-9 ]
  • 13,14-bis(4-fluorophenyl)-7H-benzo[3,4][1,2]azaborinino[1,2-a]naphtho[1,8-de][1,3,2]diazaborinine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With palladium diacetate; sodium carbonate; triphenylphosphine; lithium chloride In acetonitrile at 120℃; for 24h; Inert atmosphere; Schlenk technique;
  • 79
  • [ 24892-81-7 ]
  • [ 5216-31-9 ]
  • 1,2-bis(4-fluorophenyl)-4-phenylnaphthalene [ No CAS ]
  • 80
  • [ 83-12-5 ]
  • [ 5216-31-9 ]
  • [ 2766581-08-0 ]
YieldReaction ConditionsOperation in experiment
65% With di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; caesium acetate In tert-Amyl alcohol at 90℃; for 12h; General procedure: A mixture of 2-phenylindandione (1, 0.5 mmol), alkyne (2, 0.5 mmol), [RuCl2(p-cymene)]2 (2.5 mol%), CsOAc (0.5 mmol) in tAmOH (5.0 mL) was stirred at 90 °C under open air for 12 hours. The solvent was removed under vacuum and the crude reaction mixture was poured into water and extracted with dichloromethane (2 20 mL). The dichloromethane layer was then washed with brine, dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The crude product thus obtained was purified by silica gel (100-200 mesh) column chromatography using EtOAc/Hexane as the eluent to afford 3.
  • 81
  • [ 5216-31-9 ]
  • [ 86847-79-2 ]
  • C39H30F4N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; copper (II) acetate; anhydrous silver perchlorate In 1,2-dichloro-ethane at 120℃; for 24h; Autoclave; Inert atmosphere; 8 Implementation case 1Synthesis of N-(5,6,7,8-tetraphenyl-1-isoquinolineyl)neovaleramide 3a. General procedure: In a 20 ml pressure-resistant reaction tube, 35.6 mg of N- (2-pyridyl) neovaleramide (0.2 mmol), 78.4 mg of diphenylacetylene (0.44 mmol), 6.18 mg of [Cp*RhCl2]2(0.01 mmol), 13.7 mg of AgSbF6 were added to a20ml pressure-resistant reaction tube (0.04 mmol), 76.3 mg copper acetate (0.42 mmol), 2 ml of 1,2-dichloroethane, nitrogen protection sealed and placed in a heating agitator at 120 °C stirred for 24 hours. The reaction mixture was quenched, extracted, and dried in the organic phase with anhydrous sodium sulfate or anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure to obtain the residue, and the residue was separated by silica gel column chromatography (the elution solvent was petroleum ether / ethyl acetate) to give the target product 3a, yellow solid 57.5mg, yield 54%
54% With silver hexafluoroantimonate; bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; copper (II) acetate In 1,2-dichloro-ethane at 120℃; for 24h; Inert atmosphere; General procedure for the synthesis of Isoquinolines General procedure: 2-Aminopyridine Pivalamides 1 (0.2 mmol, 1.0 equiv), [Cp*RhCl2]2 (0.01 mmol, 5 mol%), AgSbF6 (0.04 mmol, 20 mol%), Cu(OAc)2 (0.42 mmol, 2.1 equiv), diphenylacetylene 2 (0.44 mmol, 2.2 equiv) and DCE (2 mL) were added to a 35 mL Schlenk tube. After being purged with nitrogen, the mixture was stirred at 120 °C for 24 h. Then cooled to room temperature, and quenched by adding water (2 mL). The resulting mixture was extracted with dichloromethane. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography.
  • 82
  • [ 779-30-6 ]
  • [ 5216-31-9 ]
  • 11-fluoro-8,9,14-tris(4-fluorophenyl)-6H-chromeno[4’,3’,4,5]pyrrolo[2,1-a]isoquinolin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With silver hexafluoroantimonate; bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; anhydrous silver carbonate In 1,2-dichloro-benzene at 110℃; for 5h; Inert atmosphere;
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