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[ CAS No. 2714-87-6 ] {[proInfo.proName]}

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Product Details of [ 2714-87-6 ]

CAS No. :2714-87-6 MDL No. :MFCD29066211
Formula : C13H9FO Boiling Point : -
Linear Structure Formula :- InChI Key :LBBFCPWRSLIXNI-UHFFFAOYSA-N
M.W : 200.21 Pubchem ID :85772725
Synonyms :

Safety of [ 2714-87-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:3261
Hazard Statements:H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2714-87-6 ]

* 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 [ 2714-87-6 ]

[ 2714-87-6 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 1591-31-7 ]
  • [ 2714-87-6 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper / dimethyl sulfoxide / 12 h / 60 °C / Inert atmosphere 2: potassium carbonate / methanol; water / 2 h / 20 °C / Inert atmosphere 3: xenon fluoride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 2
  • [ 73789-98-7 ]
  • [ 2714-87-6 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / methanol; water / 2 h / 20 °C / Inert atmosphere 2: xenon fluoride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 3
  • [ 73790-13-3 ]
  • [ 2714-87-6 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
1: 23 %Spectr. 2: 11 %Spectr. With xenon fluoride In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
  • 4
  • [ 92-92-2 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
94% With sodium flouride; N-(difluoro-λ4-sulfanylidene)-N-ethylethanaminium tetrafluoroborate In ethyl acetate at 20℃; for 24h; Inert atmosphere;
92% With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique;
73% With [bis(2-methoxyethyl)amino]-sulfur trifluoride In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; 1-3. Procedures of preparation of acyl fluoride 1 General procedure: Method AS3: Under N2 atmosphere, the corresponding carboxylic acid (3.00 mmol) was transferredto a PFA bottle equipped with a stirrer bar. After addition of CH2Cl2 (5.00 mL) to the bottle, the reactionmixture was cooled at 0 °C in ice bath. Then, Deoxo-fluor (0.560 mL, 3.04 mmol) was added to thesolution. The bottle was capped, and the reaction mixture was stirred at 0 °C for 5-30 min (written ateach substrate in parentheses). The reaction was quenched by addition of aqueous NaHCO3. Themixture was extracted with CH2Cl2 (10.0 mL) three times. The combined organic layer was dried overNa2SO4. Solvents were removed under reduced pressure. The crude material was purified by silica gelcolumn chromatography (hexane/AcOEt = 97:3) to give the corresponding acid fluoride.
65% With triethylamine trishydrofluoride; N-(difluoro-λ4-sulfanylidene)-N-ethylethanaminium tetrafluoroborate In dichloromethane at 25℃; for 2h;
53% With trichloroisocyanuric acid; caesium fluoride In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube;
99 %Spectr. With 2,12-di-tert-butyl-7,8-dihydro-6H-dipyrido[1,2-a:2',1'-c][1,4]diazepine-5,9-diium fluoride pentafluorosulfide In N,N-dimethyl-formamide at 90℃; Schlenk technique;
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / toluene / 4 h / 75 °C / Sealed tube 2: Palladium(0) bis(dibenzylideneacetone); (S)-Cl,MeO-BIPHEP / 1,4-dioxane / 1 h / 23 °C / Inert atmosphere; Sealed tube
Stage #1: biphenyl-4-carboxylic acid In dichloromethane at 0℃; for 0.5h; Schlenk technique; Stage #2: With [bis(2-methoxyethyl)amino]-sulfur trifluoride In dichloromethane at 0℃; for 0.5h; Schlenk technique; 3.2.2. Representative Procedure for the Synthesis of Acyl Fluorides from Carboxylic Acids General procedure: To a 20 mL of Schlenk tube charged with a magnetic stir bar, were successively added carboxylic acid (3.0 mmol) and CH2Cl2 (15 mL). After the mixture was stirred at 0 °C for 30 min, Deoxo-Fluorreagent (608 L, 3.3 mmol, 1.1 equiv) was slowly added to the reaction mixture. After the reaction mixture was stirred at 0 °C for 30 min, the solution was slowly poured into saturated NaHCO3,extracted with CH2Cl2 (3 15 mL), and dried over MgSO4. The crude product was purified by flash chromatography on silica gel to aord the corresponding acyl fluorides 1 [36].
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In tetrahydrofuran at 20℃;
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;
90 %Spectr. With pyridine; thionyl fluoride In dichloromethane at 20℃; for 0.5h;
With N-ethyl-N,N-diisopropylamine; fluoro-N,N,N′,N′-bis(tetramethylene)formamidinium hexafluorophosphate In dichloromethane at 23℃; for 0.5h; Sealed tube; Inert atmosphere;

Reference: [1]Gonay, Marie; Batisse, Chloé; Paquin, Jean-François [Journal of Organic Chemistry, 2020, vol. 85, # 15, p. 10253 - 10260]
[2]Song, Hai-Xia; Tian, Ze-Yu; Xiao, Ji-Chang; Zhang, Cheng-Pan [Chemistry - A European Journal, 2020, vol. 26, # 69, p. 16261 - 16265]
[3]Ishida, Naoyoshi; Iwamoto, Hiroaki; Sunagawa, Denise Eimi; Ohashi, Masato; Ogoshi, Sensuke [Synthesis, 2021, vol. 53, # 17, p. 3137 - 3143]
[4]Keaveney, Sinead T.; Schoenebeck, Franziska [Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4073 - 4077][Angew. Chem., 2018, vol. 130, # 15, p. 4137 - 4141,5]
[5]Liang, Yumeng; Zhao, Zhengyu; Taya, Akihito; Shibata, Norio [Organic Letters, 2021, vol. 23, # 3, p. 847 - 852]
[6]Rueping, Magnus; Nikolaienko, Pavlo; Lebedev, Yury; Adams, Alina [Green Chemistry, 2017, vol. 19, # 11, p. 2571 - 2575]
[7]Pan, Fei; Boursalian, Gregory B.; Ritter, Tobias [Angewandte Chemie - International Edition, 2018, vol. 57, # 51, p. 16871 - 16876][Angew. Chem., 2018, vol. 130, p. 17113 - 17118,6]
[8]Wang, Xiu; Wang, Zhenhua; Liu, Li; Asanuma, Yuya; Nishihara, Yasushi [Molecules, 2019, vol. 24, # 9]
[9]Malapit, Christian A.; Bour, James R.; Brigham, Conor E.; Sanford, Melanie S. [Nature, 2018, vol. 563, # 7729, p. 100 - 104]
[10]Malapit, Christian A.; Bour, James R.; Laursen, Simon R.; Sanford, Melanie S. [Journal of the American Chemical Society, 2019, vol. 141, # 43, p. 17322 - 17330]
[11]Lee, Cayo; Sammis, Glenn M.; Thomson, Brodie J. [Chemical Science, 2022, vol. 13, # 1, p. 188 - 194]
[12]Scott, Jason A.; Soto-Velasquez, Monica; Hayes, Michael P.; Lavigne, Justin E.; Miller, Heath R.; Kaur, Jatinder; Ejendal, Karin F. K.; Watts, Val J.; Flaherty, Daniel P. [Journal of Medicinal Chemistry, 2022, vol. 65, # 6, p. 4667 - 4686]
  • 5
  • [ 1082207-38-2 ]
  • [ 2714-87-6 ]
  • [ 73183-34-3 ]
  • C31H35BO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With 1,1'-bis-(diphenylphosphino)ferrocene; copper diacetate; sodium trimethylsilanolate In tetrahydrofuran at 0℃; for 3h; regioselective reaction;
  • 6
  • [ 1082207-38-2 ]
  • [ 2714-87-6 ]
  • C32H27F3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; sodium trimethylsilanolate / tetrahydrofuran / 3 h / 0 °C 2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane / 20 h / 60 °C
  • 7
  • [ 2714-87-6 ]
  • [ 120120-26-5 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
40% With potassium phosphate; [PdCl(cinnamyl)]2; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 170℃; for 16h;
37 mg With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 170℃; for 16h; Inert atmosphere; Sealed tube;
  • 8
  • [ 2714-87-6 ]
  • [ 81290-20-2 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 160℃; for 16h; Sealed tube;
  • 9
  • [ 2714-87-6 ]
  • [ 92-52-4 ]
YieldReaction ConditionsOperation in experiment
70% With triethylsilane; palladium diacetate; tricyclohexylphosphine; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 100℃; for 20h; Inert atmosphere; Sealed tube;
  • 10
  • [ 2714-87-6 ]
  • [ 3218-36-8 ]
YieldReaction ConditionsOperation in experiment
84% With triethylsilane; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 20h; Inert atmosphere; Sealed tube;
  • 11
  • [bis(difluoromethyl)zinc(dmpu)2] [ No CAS ]
  • [ 14002-51-8 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
28 %Spectr. With (S)-(-)-5,5'-dichloro-6,6'-dimethoxy-2,2'-bis(diphenylphosphino)-1,1'-biphenyl; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 23℃; for 1h; Inert atmosphere; Sealed tube;
  • 13
  • [ 14002-51-8 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
75% With potassium hydrogen difluoride; tetra-n-butyl-ammonium chloride; lithium hydroxide monohydrate In dichloromethane at 20℃; for 16h; Preparation of Acyl Fluorides 2; General Procedure General procedure: A 250 mL round-bottomed flask was charged with potassium bifluoride(15.62 g, 200 mmol) and water (40.17 g), and stirred at ambienttemperature for 1 h. Then tetrabutylammonium chloride (0.279 g, 1.0mmol, 1 mol%), DCM (used in two-fold volume of acyl chloride) andacyl chloride (1a-y; 100 mmol) were added, and the mixture wasstirred (1400 rpm) with a magnetic bar (fish; 15 × 33 mm) at r.t. forthe time given in the characterization data. The mixture was thentransferred to a separatory funnel, separated, and the aqueous phasewas extracted with DCM (50 mL). The combined organic phases werewashed with brine (50 mL), and dried with MgSO4. The mixture wasfiltered and evaporated, and the residue was distilled under reducedpressure to obtain product 2a-y.
68% With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere;
47% With potassium fluoride In acetonitrile at 20℃; for 72h; Inert atmosphere;
With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 40℃; for 24h; Schlenk technique; 3.2.1. Representative Procedure for the Synthesis of Acyl Fluorides from Acyl Chlorides General procedure: To a 50 mL of Schlenk tube charged with a magnetic stir bar, were successively added acyl chloride(4.0 mmol), 18-crown-6 (52.9 mg, 0.2 mmol, 5 mol %), KF (2.32 g, 40 mmol, 10 equiv), and THF (20 mL).After the reaction was stirred at 40 °C for 24 h, insoluble inorganic solid (KF or KCl) was filtered,and the volatiles were concentrated using a rotary evaporator. The crude product was purified by bulb-to-bulb distillation to aord the corresponding acyl fluorides 1 [35].
With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere;
With caesium fluoride In acetonitrile at 60℃;
With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere;
Multi-step reaction with 2 steps 1: triethylamine; 4‐dimethylaminopyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride / 1,2-dichloro-ethane / 18 h / 130 °C / Schlenk technique; Inert atmosphere
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl acetamide / 0 - 20 °C / Inert atmosphere 2: triethylamine trishydrofluoride / Isopropyl acetate / 2 h / 25 °C / Green chemistry

  • 14
  • [ 1006-68-4 ]
  • [ 2714-87-6 ]
  • C22H15NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; triphenylphosphine; copper(l) chloride In toluene at 80℃; for 24h; Glovebox; Sealed tube;
  • 15
  • [ 2714-87-6 ]
  • [ 17955-46-3 ]
  • [ 51533-89-2 ]
YieldReaction ConditionsOperation in experiment
82% With cesium fluoride; nickel dichloride; In toluene; at 140℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: A 20 mL dried Schlenk tube containing a stirring bar and CsF (60.8 mg, 0.4 mmol, 2 equiv) was dried with a heat gun under reduced pressure and filled with Ar after cooling to room temperature. To this vessel, were added NiCl2 (1.3 mg, 0.01 mmol, 5 mol %), toluene (1 mL), acyl fluorides (1) (0.2 mmol,1 equiv) and <strong>[17955-46-3]trimethyl(tributylstannyl)silane</strong> (2) (87.2 mg, 0.24 mmol, 1.2 equiv). The mixture was heated at 140 C with stirring for 24 h. The solution was then cooled to room temperature, and the solvent was removed under vacuum. The decarbonylative stannylation products 3 were purified by flash column chromatography on silica gel.
  • 16
  • [ 2714-87-6 ]
  • [ 75-24-1 ]
  • [ 34352-84-6 ]
YieldReaction ConditionsOperation in experiment
92% With bis-diphenylphosphinomethane In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;
  • 17
  • [ 2714-87-6 ]
  • [ 97-93-8 ]
  • [ 41658-01-9 ]
  • 4-(pentan-3-yl)-1,1'-biphenyl [ No CAS ]
  • (E)-4-(pent-2-en-3-yl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With bis-diphenylphosphinomethane In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;
  • 18
  • [ 2714-87-6 ]
  • [ 5720-07-0 ]
  • [ 13041-66-2 ]
YieldReaction ConditionsOperation in experiment
With bis(1,5-cyclooctadiene)nickel (0); diphenyl(methyl)phosphine In tetrahydrofuran at 100℃; for 16h; Inert atmosphere; Glovebox;
  • 19
  • [ 59409-55-1 ]
  • [ 2714-87-6 ]
  • [ 73183-34-3 ]
  • C30H33BO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With C37H36FeNOPS; copper diacetate; sodium trimethylsilanolate In tetrahydrofuran at 0℃; for 4h; enantioselective reaction;
  • 20
  • [ 745783-97-5 ]
  • [ 2714-87-6 ]
  • [ 18057-71-1 ]
YieldReaction ConditionsOperation in experiment
81% With copper (II)-fluoride; potassium fluoride; bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 150℃; for 24h; Schlenk technique; Inert atmosphere;
  • 21
  • [ 2714-87-6 ]
  • [ 201733-56-4 ]
  • [ 5123-05-7 ]
YieldReaction ConditionsOperation in experiment
40 mg With C42H71FNiP2 In tetrahydrofuran at 115℃; for 16h; Inert atmosphere; Sealed tube; chemoselective reaction;
  • 22
  • [ 2714-87-6 ]
  • [ 661-69-8 ]
  • [ 1625-95-2 ]
YieldReaction ConditionsOperation in experiment
77% With 1,4-bis(dicyclohexylphosphino)butane; palladium dichloride In o-xylene at 140℃; for 10h; Inert atmosphere; Schlenk technique;
  • 23
  • [ 25327-57-5 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
52% With benzoyl fluoride; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;
  • 24
  • [ 2714-87-6 ]
  • [ 81290-20-2 ]
  • [ 2369-31-5 ]
  • 2-([1,1’-biphenyl]-4-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl [1,1’-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; Trimethyl borate In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; Sealed tube;
  • 25
  • [ 2714-87-6 ]
  • [ 81290-20-2 ]
  • [ 2950-30-3 ]
  • 2-([1,1’-biphenyl]-4-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl [1,1’-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; Trimethyl borate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Sealed tube;
  • 26
  • [ 2714-87-6 ]
  • [ 91608-15-0 ]
  • [ 720-75-2 ]
  • 27
  • [ 2714-87-6 ]
  • [ 58521-27-0 ]
  • [1,1'-biphenyl]-4-yl(pentafluorophenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In 1,4-dioxane at 140℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry; chemoselective reaction;
  • 28
  • [ 498-66-8 ]
  • [ 2714-87-6 ]
  • 1,2,3,4,4a,9a-hexahydro-7-phenyl-1,4-methanofluoren-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium fluoride; palladium diacetate; tricyclohexylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere; Sealed tube;
  • 29
  • [ 2714-87-6 ]
  • [ 2170-06-1 ]
  • [ 15784-39-1 ]
YieldReaction ConditionsOperation in experiment
80% With copper(l) iodide; 1,3-bis-(diphenylphosphino)propane; palladium dichloride In N,N-dimethyl-formamide; toluene at 150℃; for 24h; Schlenk technique; Inert atmosphere;
  • 30
  • [ 2714-87-6 ]
  • [ 89343-06-6 ]
  • ([1,1'-biphenyl]-4-ylethynyl)triisopropylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With bis(1,5-cyclooctadiene)nickel (0); tributyl-amine; 1,3-bis-(diphenylphosphino)propane In 1,4-dioxane at 140℃; for 24h; Inert atmosphere; Schlenk technique; Silylated Internal Alkynes 3: General Procedure General procedure: An oven-dried 20 mL Schlenk tube containing a magnetic stirring bar was charged with Ni(cod)2 (5.5 mg, 0.02 mmol, 10mol%), DPPP (12.4 mg, 0.03 mmol, 15 mol%), 1,4-dioxane (1 mL)under dry N2, and the mixture was stirred for 30 s at r.t. The appropriate acyl fluoride 1 (0.2 mmol), silyl alkyne 2 (0.4mmol), and Bu3N (0.3 mmol) were added, and the mixture washeated at 140 °C in a heating block with stirring for 24 h, thencooled to r.t. The reaction was quenched with sat. aq NH4Cl, andthe mixture was extracted with Et2O. The combined organicphase was dried (MgSO4) and concentrated under vacuum, andthe residue was purified by column chromatography (silica gel,EtOAc-hexane).
  • 31
  • C30H18F10O [ No CAS ]
  • [ 2714-87-6 ]
  • 1-([1,1′-biphenyl]-4-yl)-2,2,3,3,3-pentafluoropropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 76 %Spectr. 2: 14 %Spectr. With cesium fluoride In benzene-d6; N,N-dimethyl-formamide at 140℃; for 4h; Inert atmosphere; 1-8. Investigation of reactivity of ester 3b under CsF catalytic system. 3b (30.0 mg, 0.0500 mmol) and ,,-trifluorotoluene (5.0 L, 0.041 mmol) were dissolved to a mix solvent of DMF and C6D6 (0.500 mL, v/v' = 4/1). After addition of CsF (1.55 mg, 0.0102 mmol) to a pressure-tight NMR tube (Wilmad-LabGlass, 524-PV-7; total volume: 2 mL), the solution was transferred to the tube. The reaction tube was heated at 140 °C for 4 h. The yields of the ketone 2b and acyl fluoride 1b were determined by 19F NMR measurement of the crude material using an internal standard.
  • 32
  • [ 116-14-3 ]
  • [ 2714-87-6 ]
  • 1-([1,1′-biphenyl]-4-yl)-2,2,3,3,3-pentafluoropropan-1-one [ No CAS ]
  • C30H18F10O [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 38% 2: 13 %Spectr. With cesium fluoride In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; 1-6. Stoichiometric reaction at 80 C and Isolation of ester 3b. Biphenyl-4-carboxylic acid fluoride (100 mg, 0.499 mmol) was dissolved into DMF (2.50 mL) as asolvent. After addition of CsF (76.0 mg, 0.500 mmol) to a pressure-tight reaction vessel (total volumeis 12 mL) as a reactor, the resulting solution was transferred to the tube. Then, TFE (2.5 atm) wascharged into the reactor. The reaction mixture was heated at 80 °C for 2 h. After, the remaining TFE was purged from the reactor, the reaction mixture was quenched by addition of water (10.0 mL). The resulting mixture was extracted with ether (10 mL) three times. The solvents were removed under reduced pressure. The yields of the ketone 2b and ester 3b were estimated by 19F NMR measurement of the crude material (2b: 13%, 3b: 47%). The crude material was purified by preparative HPLC to give the corresponding ester 3b as colorless oil in 38% yield (56.7 mg, 0.0944 mmol).
  • 33
  • [ 116-14-3 ]
  • [ 2714-87-6 ]
  • 1-([1,1′-biphenyl]-4-yl)-2,2,3,3,3-pentafluoropropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With cesium fluoride In N,N-dimethyl-formamide at 140℃; for 4h; Inert atmosphere; CsF-Catalyzed Fluoroacylation of TFE with Acyl Fluorides 1; GeneralProcedure General procedure: Under N2 atmosphere, acyl fluoride 1 (0.500 mmol) was dissolved in DMF (2.50 mL) as a solvent. After addition of CsF (3.8 mg, 0.025mmol) to a pressure-tight tube as a reactor (Wilmad-LabGlass, 513-7PVM-9; 12 mL total volume), the solution was transferred to the tube. TFE (1.5 atm, > ca. 1.1 equiv) was then charged into the reactor and the reaction mixture was heated at 140 °C for 4 h. After remaining TFE was purged from the reactor, the reaction was quenched with water (10 mL) and the resulting mixture was extracted with Et2O (3 ×10 mL). The combined organic phase was dried over Na2SO4, the solvents were removed under reduced pressure, and the crude material was purified by silica gel column chromatography (hexane/EtOAc =97:3) to give the pentafluoroethyl ketone 2. For compounds 2a, 2e,2h, and 2l-o, we present only NMR data in this section.
  • 34
  • [ 7677-24-9 ]
  • [ 2714-87-6 ]
  • [ 2920-38-9 ]
YieldReaction ConditionsOperation in experiment
98% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium iodide In toluene at 180℃; for 24h; Glovebox; Inert atmosphere; Sealed tube; Method A: Palladium-catalyzed Cyanation of Acyl Fluorides by Trimethylsilyl Cyanide (3a,Table 2) General procedure: In a glovebox filled with nitrogen, Pd2(dba)3*CHCl3 (23.8 mg, 0.023 mmol), Xantphos (34.1 mg,0.059 mmol), NaI (101.9 mg, 0.68 mmol), 1a (55.8 mg, 0.45 mmol) and 2 (67.5 mg, 0.68 mmol)were added to a 10 mL-sample vial with a Teflon-sealed screwcap. Toluene (1.5 mL) was then added,and the vial was then sealed with the cap. The vial was stirred at 180 °C for 24 h. After allowing thereaction mixture to cool to room temperature, diisopropylamine was added to the crude mixture andfiltered through a pad of silica gel and the pad was wahsed with EtOAc. The filtrate was analyzed by GC using dodecane as an internal standard.
  • 35
  • 4-iodobenzoyl fluoride [ No CAS ]
  • [ 98-80-6 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
63% With tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate In tetrahydrofuran at 40℃; for 24h; According to the literature protocol,2 1p was prepared by the reaction using Pd(PPh3)4 (116 mg, 0.1mmol), CuTC (210 mg, 1.1 mmol), phenylboronic acid (244 mg, 2 mmol), and 1o (250 mg, 1.0mmol) in THF (5 mL) at 40 °C for 24 h. After allowing the reaction mixture to cool to roomtemperature, the yield was estimated by 19F NMR (internal standard: fluorobenzene, 1p: 93%, 1o:7%).The product was isolated by silica gel column chromatography.
  • 36
  • [ 2714-87-6 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
91% With 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride; pyridine hydrofluoride In neat (no solvent) at 70℃; for 24h; Sealed tube;
  • 37
  • [ 3218-36-8 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
83% With trichloroisocyanuric acid; cesium fluoride In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube;
  • 38
  • [ 3597-91-9 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
64% With trichloroisocyanuric acid; cesium fluoride In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube;
  • 39
  • [ 2714-87-6 ]
  • [ 106-45-6 ]
  • [ 1361950-30-2 ]
YieldReaction ConditionsOperation in experiment
90% With (1,2-dimethoxyethane)dichloronickel(II); 1,3-bis-(diphenylphosphino)propane; sodium carbonate In toluene at 140℃; for 24h; Inert atmosphere; Schlenk technique; Thioethers 3; General Procedure General procedure: An oven-dried 20 mL of Schlenk tube containing a magnetic stirringbar was charged with NiCl2·DME (4.39 mg, 0.02 mmol, 10 mol%),DPPP (24.8 mg, 0.06 mmol, 30 mol%), and toluene (1 mL) under N2,which was stirred for 30 seconds at rt. Then, acyl fluoride 1 (0.2mmol), 4-methylthiophenol (2; 37 mg, 0.3 mmol), and Na2CO3 (31.8mg, 0.3 mmol) were added. The mixture was heated at 140 °C in aheating block with stirring for 24 h. After cooling to rt, the mixturewas quenched with sat. aq NH4Cl and the aqueous solution was extractedwith Et2O. The combined organic phases were dried (anhydMgSO4), and evaporated under vacuum to remove the volatiles. Theresidue was purified by column chromatography (EtOAc/hexane) onsilica gel to afford the corresponding product 3.
  • 40
  • S-(trifluoromethyl)(S)-2-(6-methoxynaphthalen-2-yl)propanethioate [ No CAS ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
65.5% With potassium fluoride; 18-crown-6 ether In dimethyl sulfoxide at 35℃; for 24h; 3 The synthesis steps and process are: add potassium fluoride (1.8mmol, 104.4mg) into a 10mL reaction tube equipped with a magnetic stirrer,18-crown ether-6 (1.8mmol, 475.2mg),Trifluoromethyl p-phenylbenzoate (1.0mmol, 282mg),Then add 4.0mL dimethyl sulfoxide, fix the reaction tube on the magnetic stirrer,The reaction was carried out in an oil bath at 35 degrees Celsius for 24 hours, and the target product acyl fluoride 1c was obtained by separation and purification with a yield of 65.5%.
  • 41
  • [ 2714-87-6 ]
  • [ 79141-00-7 ]
  • N-tert-butyl-N-isopropyl-4-phenylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Preparation of Amides 3; General Procedure General procedure: Reactions of lithium amide with acyl fluoride. A 30 mL Schlenk flaskwas charged with acyl fluoride (2.0 mmol) and flushed with argon.Then, THF (4 mL) was added, the mixture was placed in a cooling bathat -78 °C, and TMSCl (0.38 mL, 3.0 mmol) was added. To the resultingmixture a preformed solution of lithium amide in THF (see procedureabove) was added over ca. 1 min. After 30 min, the cooling bath wasremoved, the mixture was immediately quenched with saturatedaqueous NaHCO3 (20 mL), and then extracted with EtOAc (3 × 25 mL).The combined organic phases were washed with brine (25 mL), driedwith MgSO4, filtered off and evaporated. The product was purified bycolumn chromatography (cyclohexane/EtOAc v/v 20:1→10:1). Preliminaryexperiments (Scheme 3) were carried out according to theGeneral Procedure. Products of reaction with LiHMDS were isolated asN-unsubstituted amides.
  • 42
  • 4-(difluoro((trifluoromethyl)sulfonyl)methyl)-1,1'-biphenyl [ No CAS ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
With silica gel In dichloromethane at 40℃; for 0.0833333h;
  • 43
  • [ 2714-87-6 ]
  • [ 501-65-5 ]
  • [ 185990-03-8 ]
  • (Z)-(2-([1,1'-biphenyl]-4-yl)-1,2-diphenylethenyl)dimethyl(phenyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With potassium fluoride; [1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene]copper(I) triflate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 140℃; for 24h; Inert atmosphere; Schlenk technique;
  • 44
  • [ 2714-87-6 ]
  • 2-(5-amino-3-methyl-1H-pyrazol-1-yl)-6-ethylpyrimidin-4(1H)-one [ No CAS ]
  • N-(1-(6-ethyl-4-oxo-3,4-dihydropyrimidin-2-yl)-3-methyl-1H-pyrazol-5-yl)-[1,1′-biphenyl]-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.045 g Stage #1: 2-(5-amino-3-methyl-1H-pyrazol-1-yl)-6-ethylpyrimidin-4(1H)-one With lithium hexamethyldisilazane In tetrahydrofuran at 23℃; for 0.5h; Stage #2: [1,1'-biphenyl]-4-carbonyl fluoride In tetrahydrofuran; dichloromethane Heating;
  • 45
  • [ 188290-36-0 ]
  • [ 2714-87-6 ]
  • [ 34715-95-2 ]
YieldReaction ConditionsOperation in experiment
63% With trimethylsilyl trifluoropmethanesulfonate In 1,2-dichloro-ethane for 4h; Inert atmosphere;
  • 46
  • [ 2714-87-6 ]
  • (R)-alanine tert-butyl ester [ No CAS ]
  • C20H23NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane for 5h; Inert atmosphere;
  • 47
  • 1-([1,1'-biphenyl]-4-carbonyl)piperidine-2,6-dione [ No CAS ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
87% With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) In 1,2-dichloro-ethane at 130℃; for 18h; Schlenk technique; Inert atmosphere;
  • 48
  • [ 2714-87-6 ]
  • [ 3597-91-9 ]
YieldReaction ConditionsOperation in experiment
133 mg With sodium tetrahydridoborate In dichloromethane; N,N-dimethyl acetamide at 20℃; for 1h;
  • 49
  • 2-([1,1'-biphenyl]-4-carbonyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine trishydrofluoride In Isopropyl acetate at 25℃; for 2h; Green chemistry;
  • 50
  • [ 2714-87-6 ]
  • C50H74F2O3P2Pd [ No CAS ]
  • [ 1583-56-8 ]
YieldReaction ConditionsOperation in experiment
With tricyclohexylphosphine In hexadeuterobenzene at 80℃; Inert atmosphere; Glovebox;
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