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[ CAS No. 1849-25-8 ] {[proInfo.proName]}

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Chemical Structure| 1849-25-8
Chemical Structure| 1849-25-8
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Product Details of [ 1849-25-8 ]

CAS No. :1849-25-8 MDL No. :MFCD00168826
Formula : C14H11N Boiling Point : -
Linear Structure Formula :- InChI Key :ODFQRHOQXHVJTQ-UHFFFAOYSA-N
M.W : 193.24 Pubchem ID :4617269
Synonyms :

Calculated chemistry of [ 1849-25-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.27
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.44
Log Po/w (XLOGP3) : 4.1
Log Po/w (WLOGP) : 2.76
Log Po/w (MLOGP) : 3.53
Log Po/w (SILICOS-IT) : 3.19
Consensus Log Po/w : 3.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.21
Solubility : 0.0118 mg/ml ; 0.0000612 mol/l
Class : Moderately soluble
Log S (Ali) : -4.35
Solubility : 0.00859 mg/ml ; 0.0000444 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.64
Solubility : 0.00442 mg/ml ; 0.0000229 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.05

Safety of [ 1849-25-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1849-25-8 ]

* 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 [ 1849-25-8 ]

[ 1849-25-8 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 1942-30-9 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride; tin In water monomer at 60℃; for 6h;
93% With nickel In N,N-dimethyl-formamide for 0.25h; Ambient temperature;
93% With 4,4'-bipyridine; tetrahydroxydiborane In N,N-dimethyl-formamide at 20℃; for 0.0833333h; chemoselective reaction;
91% With tris(triphenylphosphine)ruthenium(II) chloride; potassium hydroxide; zinc powder In 1,4-dioxane; water monomer at 40℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;
83% With iron sulphate heptahydrate In methanol; water monomer for 11h; Reflux;
75% With hydrazine hydrate monohydrate at 80℃; for 0.416667h; Microwave irradiation; chemoselective reaction; Typical experimental procedure for microwave-induced transfer hydrogenation of nitro arenes using SS-Rh catalyst A mixture of 1e (100 mg, 0.81 mmol), hydrazine hydrate (121.5mg, 2.43 mmol), and SS-Rh (370 mg, 2 mol% Rh) were taken in an oven dried reaction tube equipped with screw cap. 0.5 ml of PEG-400 was added into the reaction mixture. The reaction was then irradiated in a microwave apparatus at 80°C , 80 W for 10 min with a pressure of 80 Psi. After cooling to ambient temperature in the microwave cavity the reaction mixture was extracted with ethyl acetate (3x2 ml) and water (1ml). The combined organic layer wasdried over anhydrous Na2SO4 and the solvent was removed under reduced pressure and afterpurification with silica gel column chromatography (hexane: EtOAc::95:5) 2e as white solid (65 mg, 75%), m.p. 124-126°C; 1H NMR (300 MHz; CD3OD) δ 6.66-6.68 (d, J = 6.75 Hz, 2H), 7.23-7.24 (d, J = 1.92, 2H), 7.26-7.36 (m, 3H), 7.43-7.46(m, 2H); 13C NMR (75 MHz; CD3OD) δ 88.35, 92.21, 113.36,116.49 (2C), 126.28, 129.33, 130.15 (2C), 132.88 (2C), 134.45 (2C), 150.56.ESI-MS: m/z (M+H).+ ESI-MS: m/zcalc. for (M+H)+ C14H11N 194.2512 and obsd. 194.2535.
65% With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; chemoselective reaction;
With phenylhydrazine
With stannous chloride
With hydrogenchloride; zinc powder
With hydrogenchloride; tin In ethanol

Reference: [1]Kalashnyk, Nataliya; Ganeshnagaswaran, Praveen; Kervyn, Simon; Riello, Massimo; Moreton, Ben; Jones, Tim S.; Devita, Alessandro; Bonifazi, Davide; Costantini, Giovanni [Chemistry - A European Journal, 2014, vol. 20, # 37, p. 11856 - 11862]
[2]Yasuhara; Kasano; Sakamoto [Journal of Organic Chemistry, 1999, vol. 64, # 7, p. 2301 - 2303]
[3]Han, Min Su; Jang, Mingyeong; Lim, Taeho; Park, Byoung Yong [Journal of Organic Chemistry, 2022, vol. 87, # 2, p. 910 - 919]
[4]Schabel, Tobias; Belger, Christian; Plietker, Bernd [Organic Letters, 2013, vol. 15, # 11, p. 2858 - 2861]
[5]Yang, Wang-Yong; Breiner, Boris; Kovalenko, Serguei V.; Ben, Chi; Singh, Mani; LeGrand, Shauna N.; Sang, Qing-Xiang Amy; Strouse, Geoffrey F.; Copland, John A.; Alabugin, Igor V. [Journal of the American Chemical Society, 2009, vol. 131, # 32, p. 11458 - 11470]
[6]Guha, Nitul Ranjan; Bhattacherjee, Dhananjay; Das, Pralay [Tetrahedron Letters, 2014, vol. 55, # 18, p. 2912 - 2916]
[7]Zhao, Lixing; Hu, Chenyang; Cong, Xuefeng; Deng, Gongda; Liu, Liu Leo; Luo, Meiming; Zeng, Xiaoming [Journal of the American Chemical Society, 2021, vol. 143, # 3, p. 1618 - 1629]
[8]Litwinenko; Lewtschenko; Androssow [Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2046][Chem.Abstr., 1959, p. 2154]
[9]Haddow et al. [Philosophical transactions of the Royal Society of London. Series A, Mathematical and physical sciences, 1948, vol. 241, p. 147,187]
[10]Veschambre,H. et al. [Bulletin de la Societe Chimique de France, 1967, p. 134 - 139]
[11]Dombrovskii,A.V.; Taschchuk,K.G. [Journal of general chemistry of the USSR, 1963, vol. 33, p. 158 - 162][Zhurnal Obshchei Khimii, 1963, vol. 33, # 1, p. 165 - 170]
  • 2
  • [ 75-44-5 ]
  • [ 1849-25-8 ]
  • 1-Isocyanato-4-phenylethynyl-benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine In toluene for 2h; Heating;
  • 3
  • [ 536-74-3 ]
  • [ 540-37-4 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
99% With CuI(xantphos); Cs2CO3 In N,N-dimethyl-formamide at 135℃; for 0.5h; Inert atmosphere; Microwave irradiation;
99% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine at 20℃; Schlenk technique; Inert atmosphere;
98% With potassium carbonate; copper chloride (I) In methanol; acetonitrile at 25 - 30℃; for 4h; Inert atmosphere; Irradiation;
98% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 3h;
97.5% With tripotassium phosphate tribasic; palladium In 2-methoxy-ethanol; lithium hydroxide monohydrate at 80℃; for 4h; 4 Iodobenzene 2.04 g (0.01 mol), phenylacetylene 1.53 g (0.015 mol), potassium phosphate 4.22 g (0.02 mol) were added to a round bottom flask of 50mL capacity purged with nitrogen, equipped with stirrer, thermometer, reflux condenser, then methyl cellosolve / water (1: 1) 20 mL was weighed and added. Then, alkali aqueous solution 10.02g containing palladium nanoparticle catalysts from synthesized in Production Example 1 (Pd amount relative iodobenzene is 0.01 mol%) was added and heated in an oil bath and heated to reflux for 8 hours at 80 . After completion of the reaction, adding toluene 15mL and water 10 mL, the organic layer was separated. The organic layer was concentrated with an evaporator, and the resulting concentrated residue purified by silica gel column chromatography to obtain the target compound
96% Stage #1: 1-ethynylbenzene With piperidine; indium(III) bromide at 20℃; for 2.5h; Stage #2: p-aminoiodobenzene With piperidine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) at 20℃; for 1.5h;
96% With potassium carbonate In lithium hydroxide monohydrate at 20℃; for 3h;
95% With copper oxide (I); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 135℃; for 12h; Inert atmosphere;
95% With copper (I) iodide; potassium carbonate In ethanol; lithium hydroxide monohydrate at 90℃; for 10h; Green chemistry; General procedure for Sonogashira reaction General procedure: A mixture of arylhalide (1 mmol), phenylacetylene (1 mmol), CuI(2 mol%), K2CO3(1 mmol), and nano Pd/ZnO (0.009 g) in H2O (1 mL)was stirred at 90C for the appropriate time. In the case of the sub-strates which are insoluble in water, a mixture of H2O/EtOH (1:1)was used as solvent. The progress of the reaction was monitored byTLC or GC. The separation of the catalyst from the reaction mixture and the work-up process is similar to the section 2.3.All compounds were known and characterized by comparison of their physical and spectroscopic data with the data already described in the literature.
94% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine In tetrahydrofuran at 20℃;
93% With N-ethyl-N,N-diisopropylamine In lithium hydroxide monohydrate for 4h; Reflux; Green chemistry;
92% With sodium hydroxide at 250℃; for 2.77778E-05h;
92% With triethylamine In acetonitrile at 82℃; for 3h; General procedure for Heck and Sonogashira coupling reactions General procedure: Aryl halide (1 mmol), alkene or alkyne (1.2 mmol), triethylamine (3 mmol) and 25 mg (0.07 mol%) Pd0-Mont. were added to 10 ml acetonitrile solution and the reaction mixture was stirred at 82 ◦C for stipulated time period. The progress of the reactions was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and the solid catalyst was separated from the mixture by filtered through sintered funnel (G-3). The recovered catalyst was washed with acetone, dried in a desiccator and stored for another consecutive reaction run. The product was extracted with ethyl acetate followed by evaporation of the solvent to yield the crude product which was finally purified by silica gel column chromatography using ethyl acetate and hexane as eluents. The products were identified by 1H NMR, mass spectrometry and melting point determination followed by their comparison with the standard literature data [45].
91% With copper (I) iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 1h;
91% With copper (I) iodide; palladium diacetate; triethylamine; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
91% With [Cu(N-(2-quinolynylmethylene)-1H-benzimidazole)(PPh3)2]PF6; potassium carbonate In toluene at 90℃; for 16h; Inert atmosphere; 2.4 Catalytic activity for the Sonogashira coupling of phenylacetylene with aryl halides General procedure: The Sonogashira coupling reaction of phenylacetylene with different aryl halides catalyzed by copper(I) complexes was carried out according to the procedure: 10mol% of copper(I) catalyst was added to 2mmol of respective aryl halide, 2.5mmol of phenylacetylene, 2mmol of K2CO3 in toluene and the reaction mixture was stirred for 16h at 90° under nitrogen. The reaction mixture was then cooled to room temperature and the solution was filtered to remove the precipitated base. The filtrate was concentrated and crude product was purified by column chromatography using ether:chloroform (9:1). The purified product obtained was characterized by elemental analyses, IR, 1H NMR and mass spectral studies.
91% With potassium carbonate In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 90℃; for 3h;
90% With potassium hydroxide; copper (I) iodide; triphenylphosphine In isopropanol at 80℃; for 5h;
90% With palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate at 20℃; for 5h;
90% With C16H20Cl2N2O2Pd; potassium hydroxide In lithium hydroxide monohydrate; acetonitrile at 20℃; for 3h; 31. General procedure for Sonogashira coupling reaction General procedure: In a 10 mL round bottom flask, the palladium complex (0.010 mmol) was dissolved in acetonitrile (2 mL). Aryl halide (1.0 mmol), alkyne (1.2 mmol), KOH (2.00 mmol) and distilled water (2 mL) were added. The mixture was stirred at room temperature (or 60° C) for the required time. After reaction completion, the product was extracted with ethyl acetate (3x5 mL). The combined organic layers were dried with anhydrous sodium sulfate. The product was analyzed with GC and GC-MS. The product was purified using column chromatography with hexane-ethyl acetate as eluent. The characterization data were in entire agreement with the previously reported literature.32-39
90% With triethylamine In lithium hydroxide monohydrate at 90 - 100℃; for 2h;
90% With potassium hydroxide In lithium hydroxide monohydrate; acetonitrile at 60℃; for 5h; 7 Example 7
Catalytic Activity of Palladium Bis(Oxazoline) Supported on Merrifield Resin (Pd-BOX) in Sonogashira Cross Coupling Reactions General procedure: In a general procedure for Sonogashira cross coupling reactions a mixture of aryl halide (1.0 mmol), alkyne (1.5 mmol), KOH (2.00 mmol), acetonitrile (2 mL) and distilled water (2 mL) were added together to a flask. Immobilized palladium bis(oxazoline) catalyst contained in a dialysis bag (0.0050 mmol) was introduced. The mixture was stirred at 60° C. for the required time. After completion of the reaction, the catalyst bag was removed and dialyzed in acetonitrile to extract all the products. The combined solutions were extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure in a rotary evaporator. The residue was purified using column chromatography with hexane-EtOAc as eluent to afford the cross coupling product in an excellent yield.
90% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 13h; Green chemistry; 2.5 General method for Sonogashira coupling reaction General procedure: A mixture of aryl halide (1mmol), terminal alkyne (1mmol), K2CO3 (2mmol) and MNPFemTriazNHCAg complex (6) (100mg) in DMF (5mL) was stirred at 100°C. The progress of reaction was monitored by TLC. After completion, the reaction mixture was quenched in ice cold water and 6 was separated by external magnet. The reaction mixture was extracted with ethyl acetate (3×25mL). Evaporation of solvent in vaccuo followed by column chromatography over silica gel using petroleum ether/ethyl acetate afforded desired Sonogashira coupling products.
89% With potassium carbonate In ethanol at 78℃; for 10h;
89% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;
89% With palladium diacetate; C52H44Cu4F8I4P4; triethylamine at 20℃; for 0.25h;
88% With sodium hydroxide In lithium hydroxide monohydrate; propan-2-one at 60℃; for 1h;
88% With C21H15N3O4Pd; potassium carbonate In isopropanol at 25℃; for 15h;
88% With potassium carbonate In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 90℃; for 2h;
88% With piperidine In neat (no solvent) at 90℃; for 2.5h; Green chemistry; 2.4. General procedure for Sonogashira cross coupling reactions General procedure: Aryl halide (1 mmol), alkyne (1.1 mmol), piperidine (2 mmol)and the Fe3O4(at)SiO2-NHC-Pd() catalyst (0.007 g, 0.43 mol%) wasstirred at 90 °C for the appropriate time as indicated in Table 5 andreaction progress was confirmed by TLC. After completion of thereaction, the reaction mixture was diluted with ethyl acetate(10 mL) and the catalyst was separated with an external magnet.Solvent was evaporated under reduced pressure and the cruderesidue was then purified by column chromatography using ethylacetate/hexane as an eluent to give the desired Sonogashira product(5a-5ak; Table 5).
88% With manganese powder In ethanol for 3.83333h; Reflux; Green chemistry;
87% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 20℃; for 15h; Schlenk technique; Inert atmosphere;
87% With C53H46CuN4OP2(1+)*F6P(1-); potassium carbonate In toluene at 90℃; for 16h; Inert atmosphere; 2.4. Catalytic activity for the Sonogashira coupling of phenylacetylenewith aryl halides General procedure: The Sonogashira coupling reaction of phenylacetylene with aryl halides catalyzed by copper(I) complexes was carried out according to the procedure: 10 mol% of copper(I) catalyst was added to 2 mmol of respective aryl halide, 2.5 mmol of phenylacetylene, 2 mmol of K2CO3 in toluene and the reaction mixture was stirred for 16 h at 90° under nitrogen. The reaction mixture was then cooled to room temperature and the solution was filtered to remove the precipitated base. The filtrate was concentrated and crude product was purified by column chromatography using ether: chloroform (9:1). The purified product was then characterized by elemental analyses, IR, 1H NMR and mass spectral studies.
87% With potassium carbonate In ethanol; lithium hydroxide monohydrate at 60℃; for 2.4h;
86% With Cu(acac)<SUB>2</SUB> H<SUB>2</SUB>O; potassium carbonate; dimethyl sulfoxide at 140℃; for 24h; Inert atmosphere;
86% With triethylamine In acetonitrile at 85℃; for 3h; 2.3.4 General procedure for Heck/Sonogashira coupling reaction General procedure: Aryl halide (1 mmol), alkene/alkyne (1.2 mmol), triethylamine (3 mmol) and 25 mg (0.05 mol%) Pdo-catalyst (Pd-1 or Pd-2) were added to 10 ml acetonitrile solution and the reaction mixture was stirred at 85 °C for stipulated time period. The progress of the reactions was monitored by TLC. After completion of the reaction, the mixture was cooled to r.t. and the product was extracted with ethyl acetate followed by evaporation of the solvent to yield the crude product which was finally purified by silica gel column chromatography using ethyl acetate and hexane as eluents. The products were identified by 1H NMR, mass spectrometry and melting point determination followed by their comparison with the standard literature data [39,40].
86% With copper oxide (I); Cs2CO3 In N,N-dimethyl-formamide at 135℃; for 24h; Inert atmosphere; General Procedure for the Synthesis of Compounds 3a-e General procedure: A sealable vial equipped with a magnetic stir bar wascharged with Cs2CO3 (652 mg, 2.0 mmol) and Cu2O (7.0 mg,0.05 mmol) under a nitrogen atmosphere. The aperture of thevial was then covered with a rubber septum. Under a nitrogen atmosphere, aryl alkyne 1 (1.5 mmol), aryl iodide 2 (1.0 mmol), and DMF (0.5 mL) were added by syringe. The septum was then replaced by a screw cap containing a Teflon-coated septum, and the reaction vessel was placed at 135 °C. After stirring at this temperature for 24 h, the heterogeneous mixture was cooled to r.t. and diluted with EtOAc (20 mL). The resulting solution was filtered through a pad of silica gel, then washed with EtOAc (20 mL), and concentrated to give the crude material which was then purified by column chromatography on silica gel to yield alkyne 3.
86% With C65H53CuN4P3(1+)*F6P(1-); potassium carbonate In toluene at 90℃; for 16h; Inert atmosphere; Sonogashira coupling reactions General procedure: The coupling of phenylacetylene with aryl halides catalyzedby these copper(I) complexes was carried outaccording to the following procedure: The copper(I) catalyst(10 mol %) was added to the respective aryl halide(2 mmol), phenylacetylene (2 mmol), and K2CO3(2 mmol) in toluene (10 ml), and the reaction mixture wasstirred for 16 h at 90 C under nitrogen. The reactionmixture was then cooled to room temperature, and thesolution was filtered to remove the precipitated base. Thefiltrate was concentrated to dryness, and the crude productwas purified by column chromatography using ether/chloroform(9:1). The purified product was then characterizedby elemental analyses, IR, 1H NMR and mass spectralstudies.
85% With copper (I) iodide; C26H24N6NiS4; triethylamine In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; Typical procedure for the Sonogashira reaction of aryl iodides with phenylacetylene General procedure: In an oven-dried round bottom flask under an atmosphere of N2, a mixture of aryl halide (1 mmol), phenylacetylene (1.5 mmol), 1 (60.75 ppm or 0.05 mol%), copper(I) iodide (5 mmol), and Et3N (3.0 mmol) in DMF (5 mL) was taken. The reaction mixture was stirred 80 °C for 2 h. At the end of the mentioned time, the reaction mixture was diluted with EtOAc (20 mL), washed with water (3 x 10 mL). The combinedorganic layer was dried over anhydrous Na2SO4, filtered and stripped off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel using ethyl acetate and n-hexane mixtures to afford the desired product in high purity. The products were characterized by 1H and 13C NMR analysis.
85% With potassium carbonate In ethanol at 100℃; for 4h; Sealed tube; Inert atmosphere; Green chemistry;
85% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 80℃; Sealed tube; Inert atmosphere;
85% With tripotassium phosphate tribasic; copper (I) iodide; dimethylsulfone at 110℃; for 14h; Inert atmosphere; Green chemistry;
83% With 2-aminophenyl diphenylphosphinite; palladium diacetate; sodium hydroxide In lithium hydroxide monohydrate at 80℃; for 4h;
82% With triethylamine In tetrahydrofuran at 20℃; for 16h; 2.A.A To a mixture of 4-iodoaniline (8) (440 mg, 2 mmol), copper iodide (7.6 mg, 0.04 mmol) and dichlorobis(triphenylphosphine)palladium (II) (14 mg, 0.02 mmol) in THF (5 mL) was added phenylacetylene (244.8 mg, 2.4 mmol) and triethylamine (556 uL, 4 mmol). The reaction vessel was flushed with argon, and the reaction mixture stirred at room temperature for 16 hours. LC-MS analysis of the reaction indicated that the reaction was complete. Ethyl acetate (5 mL) was added, and the precipitates removed by passing through a plug of celite. The filtrate was concentrated, and the crude purified by flash column chromatography (SiO2, 6% ethyl acetate in hexanes) to afford compound 9 as a brown solid (321 mg, 82% yield). HPLC-MS tR=1.88 min (UV254 nm); mass calculated for formula C14H11N 193.1, observed LCMS m/z 194.1 (M+H).
82% With triethylamine In tetrahydrofuran at 20℃; for 18h; 3.A Example 3:; Example 3A:; Part A:; To a mixture of 4-iodoaniline (7) (440 mg, 2 mmol), copper iodide (7.6 mg, 0.04 mmol) and dichlorobis(triphenylphosphine)palladium (II) (14 mg, 0.02 mmol) in THF (5 ml_) was added phenylacetylene (244.8 mg, 2.4 mmol) and triethylamine (556 μl_, 4 mmol). The reaction vessel was flushed with argon, and the reaction mixture stirred at room temperature for 18 hours. LC-MS analysis of the reaction indicated that the reaction was complete. Ethyl acetate (5 ml_) was added, and the precipitates removed by passing through a plug of celite. The filtrate was concentrated, and the crude purified by flash column chromatography (SiO2, 6 % ethyl acetate in hexanes) to afford compound 8 as a brown solid (321 mg, 82 % yield). HPLC-MS tR = 1.88 min (UV254 nm); mass calculated for formula Ci4HnN 193.1 , observed LCMS m/z 194.1 (M+H).
81% With [(Pd{(κ2-C,N)-(3-(dimethylaminomethyl)indole)}µ-OAc)2]; potassium carbonate In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 100℃; for 5h; General procedure for the Sonogashira reaction General procedure: A 50-mL round-bottom flask was charged with aryl halide (1 mmol), phenylacetylene (1.5 mmol), K2CO3 (2 mmol), DMF:H2O (1:1) (4 mL), and the C,N-palladacycle (0.1 mol% Pd). The mixture was stirred at 100°C for the desired reaction time. The reaction was monitored by GC. After the reaction was complete, the mixture was cooled to room temperature and diluted with EtOAc and H2O. The product was extracted with EtOAc and the organic phase dried over MgSO4, filtered, and concentrated. The arylalkynes obtained could be purified by silica gel column chromatography (hexane:EtOAc).The arylalkyne products were known compounds and were characterized from their 1H NMR and 13C NMR.
79% With tripotassium phosphate tribasic; diethylzinc(II); N<SUB>1</SUB>,N<SUB>2</SUB>-dimethylethane-1,2-diamine In 1,4-dioxane at 125℃; for 48h; Sealed tube; Inert atmosphere; Synthesis of 1-4-phenylethynylphenylethanone General procedure: A dry sealed tube was charged with 1.1 mmol (271mg) of 4-iodoacetophenone and 2 equiv. of K3PO4(424 mg). To the above mixture was added 1 mmol of phenylacetylene (102 mg,0.109 ml), 5 mol % of Et2Zn (0.05 ml), 10 mol % of DMEDA (0.01 ml)and 3 ml of 1,4-dioxane under nitrogen. The sealed tube was heated in an oilbath which was preheated to 125 °C and the reaction mixture was stirred under the same conditions for 48 hours. The reaction mixture was then cooled and extracted with ethyl acetate (3 x 15 ml) and the ethyl acetate layer was washed with distilled water. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure in a rotary evaporator. The crude residue was purified by column chromatography using hexane-EtOAc (49:1) as the eluent to get 165 mg (75 %) of the product as colourless solid.
78% With sodium hydroxide; palladium (II) chloride at 20 - 80℃; for 1.45h; Green chemistry; General procedure for the sonogashira couplingreaction of aryl halides and phenylacetyenein the presence of PdCl2/DPPPEG200 in PEG200 General procedure: A round-bottom flask was charged with phenylacetylene(1.5 mmol, 0.16 mL), NaOH (1.5 mmol, 100 mg), PEG200(2 mL), and aryl halide (1.0 mmol). To this mixture,3.0 mol% of PdCl2 and 8.0 mol% of DPPPEG200 wereadded. The reaction mixture was placed in an 80 C oilbath and stirred to complete. The completion of the reactionwas monitored by TLC. After completion of reaction,the mixture was cooled to room temperature, and the catalystwas removed by addition of Et2O and then centrifugated.The isolated catalyst was dried and reused. Thefiltered solution was evaporated reduced pressure, and theexpected product was purified by column chromatographyover silica gel [60 Merck (230-240 mesh)] using petroleumether/ethyl acetate (5:1) as eluent to afford the product withhigh purity in 58-95 % yield.
78% With potassium carbonate In ethanol; lithium hydroxide monohydrate at 20℃; for 5h; Irradiation;
77% With Cs2CO3 In methanol at 80℃; for 24h;
75% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 60℃; Inert atmosphere;
75% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;
73% With potassium carbonate for 5h; Heating; Green chemistry; General Procedure for the Sonogashira Coupling Reaction of Aryl Halides and Phenylacetyenein the Presence of Pd(0)/SDPP General procedure: A round-bottom flask was charged with phenylacetylene (0.75 mmol, 0.08 mL), K2CO3 (0.75 mmol, 100 mg), PEG 200 (1 mL), and aryl halide (0.5 mmol). To this mixture, Pd(0) nano-catalyst supported on SDPP (1.5 mol-%, 3.0 mg) prepared according to our previous report [13] was added. In the case of aryl iodides and activated aryl bromides, the reaction mixture was placed in a 100 °C oil bath; and in the case of the less active and deactivated aryl bromides and chlorides, the reaction mixture was placed in a 120 °C oil bath. After completion of the reaction, the catalyst was removed by centrifugation and the remaining mixture was extracted with ethyl acetate (310 mL) and water several times and dried over anhydrous Na2SO4. The organic layer was evaporated under reduced pressure, and then purified by column chromatography over silica gel 60 (230-240 mesh; Merck) using petroleum ether/ethyl acetate (5 : 1) as eluent to afford the product with high purity in 51-95% yield. Note: This procedure can also be used, but the catalyst is prepared in situ by adding the appropriate amounts of SDPP and Pd(OAc)2.
72% With copper (I) iodide; triethylamine at 20℃;
72% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 30℃; Inert atmosphere;
70% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In lithium hydroxide monohydrate for 24h; Reflux; Synthesis of 4-phenylethynylaniline (PHE) The synthesis of PHE proceeded via Pd(PPh3)2Cl2/CuI (5 mmol%)-catalysed coupling of 4-iodoaniline (1 g, 4.56 mmol) with two molar equivalents of phenylacetylene (1 g, 9.13 mmol). The reaction was refluxed using water as the solvent and triethylamine as a base under ambient atmosphere for ca. 24 h, forming two layers of solution. The organic phase was collected, dried over sodium sulphate, and evaporated to dryness. The crude product obtained was then purified via column chromatography, eluted with a mixture of hexane and dichloromethane (7:3). Evaporation of the solvents afforded the product PHE as a brown solid (70% yield). 1H NMR (400.11 MHz, CDCl3): δ 3.83 (s br, 2H, NH2); 6.67 (pseudo-d, JHH = 9 Hz, 2H, C6H4); 7.52 (pseudo-d, JHH = 9 Hz, 2H, C6H4); 7.29-7.39 (m, 5H, C6H5);13C NMR (100.61 MHz, CDCl3): δ 87.3, 90.1 (2 * s, 2 * C≡C); 112.6, 114.7, 123.9, 127.6, 128.2, 131.3, 132.9, 146.6 (8 * s, Ar); Elemental analysis for C15H10N2: [Found (Calcd.)]: C = 86.51 (87.01); H = 5.53 (5.74); N = 7.24 (7.25).
68% With triethylamine In toluene at 80℃; for 10h;
62% With bis(cyclohexylisocyanide)palladium(II) chloride; potassium carbonate; benzoic acid hydrazide In ethanol at 80℃; for 2h; Sonogashira reaction (general procedure). General procedure: A solution of comple 1 in ethanol with a required concentrationwas added with stirring to a mixture of iodoarene2a-2g (0.3 mmol), phenylacetylene (3, 0.5 mmol),potassium carbonate (0.7 mmol), and ethanol (2 mL). The mixture was heated for 2 h on an oil bath at a bathtemperature of 80°C. After cooling to room temperature,the mixture was diluted with 10 mL of waterand extracted with hexane-methylene chloride (5 : 1,2 × 5 mL), and the combined extracts were dried overanhydrous sodium sulfate and analyzed by GC/MS.The solvent was evaporated, and the product wasisolated by silica gel column chromatography usingn-hexane as eluent.The properties of the isolated compounds were inagreement with the data given in [23-27].
57% With C19H25CuN5(1+)*F6P(1-); potassium carbonate In N,N-dimethyl-formamide at 135 - 140℃; Sealed tube; 4.4 Cu-catalyzed coupling of aryl iodide and phenylacetylene derivatives General procedure: A 20mL scintillation vial was charged with a Teflon stir bar, copper complex (0.1mmol), 76 potassium carbonate (0.75mmol), aryl iodide (0.5mmol), 77 phenylacetylene (0.75mmol) in 5mL non-anhydrous DMF in air. The vial was sealed and placed in an oil bath with pre-adjusted temperature at 135-140°C. After the allowed time, the reaction mixture was cooled down, diluted with 25-30mL ethyl acetate, and filtered through a pad of silica gel. The solvent was then removed under vacuum and the residue was purified by column chromatography using mixtures of hexane and ethyl acetate to obtain analytically pure product.
54% With tetrahydropyrrole at 85℃; for 3h;
50% With palladium diacetate; potassium carbonate; urea In ethanol at 20℃; for 8h; General experimental procedure for Sonogashira reaction General procedure: In a 50ml round bottom flask, a mixture of aryl halide (0.5mmol), acetylene (0.75mmol), Pd(OAc)2 (1mol%), Urea (0.25mmol) and K2CO3 (1.5mmol) in EtOH (4ml) were added and stirred at room temperature. After completion (monitored by TLC); the reaction mixture was extracted with ethyl acetate (10ml×3) and the combined organic layer was washed with brine (20ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using n-hexane as eluent to give the corresponding diarylalkyne. The desired products are characterized by comparing 1H, 13C NMR data with authentic samples.
50% With palladium diacetate In ethanol at 60℃; for 8h; Green chemistry; General experimental procedure for Sonogashira reaction General procedure: A mixture of aryl halide (1 mmol), terminal acetylene (1.5 mmol) and Pd(OAc)2 (1 mol%) in WEB:Ethanol (1:1, 8 mL) was stirred for the indicated time at 60 °C. After completion of the reaction (vide TLC), the reaction solution was extracted with ethyl acetate (4 × 10 mL). The products were purified by column chromatography over silica gel using n-hexane-ethyl acetate (9 : 1, v/v) to obtain the desired coupling products. The products were characterized using 1H and 13C-NMR spectroscopy and GC-MS.
40% With palladium diacetate In ethanol at 20℃; for 12h; Green chemistry;
38% With copper (I) iodide; Pd(2+)*C27H26P2*2CF3O3S(1-)*C22H16N4*H2O; triethylamine In lithium hydroxide monohydrate at 100℃; for 2h; Microwave irradiation; 2.4 Microwave-assisted Sonogashira cross-coupling reaction of aryl halides with phenylacetylene General procedure: A mixture of the aryl halide (1mmol), phenylacetylene (1mmol), copper(I) iodide (7mol%), compound 1 (5mol%), TEA (1.2mmol) and H2O (5mL) in a microwave reaction vial was heated under microwave conditions in air at 100°C for 2h and then cooled to room temperature. The crude product was purified by column chromatography. All coupled products were treated by a similar workup (for the NMR spectra and melting points of the products, see the supporting information).
With tripotassium phosphate tribasic; C28H47ClN4P2Pd In 1,4-dioxane; ethylene glycol at 140℃; for 0.25h; Inert atmosphere;
With 1,4-diaza-bicyclo[2.2.2]octane at 130℃; for 48h; chemoselective reaction;
Stage #1: p-aminoiodobenzene With copper (I) iodide; palladium diacetate; triethylamine; triphenylphosphine In dichloromethane for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 1-ethynylbenzene In dichloromethane at 50℃; Inert atmosphere;
With tetrakis-(triphenylphosphine)-palladium; C18H14O3PS(1-)*C36H30NP2(1+); triethylamine In dichloromethane for 0.166667h;
With palladium catalyst
23 %Spectr. With tetrahydropyrrole; [(NC5H2(CO2H)(C3H2N2C3H6CO2H)2)PdBr](1+)*Br(1-)=[(NC5H2(CO2H)(C3H2N2C3H6CO2H)2)PdBr]Br In lithium hydroxide monohydrate at 50℃; for 24h;
0.5 g With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 12h; 1 Production of 4-(2-phenyl-1-ethynyl)aniline (Compound 4-1) Dimethylformamide (10 ml), 10 ml of triethylamine, 0.93 g of phenylacetylene, 0.32 g of palladium chloride-ditriphenylphosphine complex, and 0.09 g of copper iodide were added to 1.0 g of 4-iodoaniline, and the mixture was stirred at 50° C. for 12 hours. After completion of the reaction, water was added to the reaction solution, and extraction was performed 3 times with ethyl acetate. The organic layer was collected, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), thereby obtaining 0.50 g of 4-(2-phenyl-1-ethynyl)aniline (Compound 4-1).
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In benzene at 70℃; Inert atmosphere; General procedure of syntheses of aminoacetylenes 3 General procedure: mixture of 4-iodaniline (3mmol),corresponding alkyne-1 (3.2 mmol), PdCl2(PPh3)2 (10 mg), CuI (5 mg) and Et3N (2 mL) inbenzene (25 mL) was stirred at 70 C under the argon atmosphere. When the coupling wascomplete (TLC control) the products 3 was separated by column chromatography using hexaneand then hexane-ethylacetate mixtures as eluent and recrystallized. Spectroscopic data andmelting points for 4-(p-methoxyphenyl)ethynylaniline (3d),29 4-phenylethynylaniline (3b),30 nbutylethynylaniline(3c),31 and p-aminophenylacetylene (3a)32 were consistent with the literaturedata.
34 %Chromat. With C18H18N2O8PdS2(2-)*2Na(1+)*3H2O; triethylamine In lithium hydroxide monohydrate at 80℃; for 1h;
With potassium carbonate In ethanol at 75℃; for 7h; Green chemistry; 2.5. General procedure for the Sonogashira cross-coupling reaction General procedure: An aryl halide (1 mmol) and phenylacetylene (1.5 mmol)were added to a mixture of Fe3O4/oleic acid/Pd catalyst (0.005mmol) and K2CO3 (2 mmol) in ethanol (6 mL) as solvent in aglass flask under vigorous stirring. The mixture was refluxed at75 °C for 6 h under aerobic conditions. The palladium catalystwas recovered by a simple magnet and reused for the next run.The solution was washed with ethanol and deionized water (10mL) and dried in a vacuum oven at 60 °C.
100 %Chromat. Stage #1: 1-ethynylbenzene; p-aminoiodobenzene With tetrahydropyrrole In N,N-dimethyl-formamide at 79.84℃; for 4h; Stage #2: In N,N-dimethyl-formamide
With potassium hydroxide In N,N-dimethyl-formamide at 150℃; for 12h; Inert atmosphere; 2.2. Sonogashira cross-coupling reaction General procedure: The cross-coupling reaction was performed in a 25 mL stainless steel reactor. 1.1 mmol phenylacetylene, 1 mmol iodobenzene or one of its derivatives, 2 mmol KOH, 10 mL N,N-Dimethylformamide (DMF) and 50 mg Cu2O/RGO were added into the reactor. After purging the reactor with Ar gas, the reaction was carried out at 150 °C for 12 h. After that, the reaction mixture was collected and centrifuged to separate the catalyst and the supernatant. The supernatant was analyzed by BRUKER SCION SQ 456 GC-MS to measure the concentration changes of reactants and products. The quantitative analysis of product was detected by single ion monitoring mode in GC-MS.
19 %Chromat. With 1,3-bis(2-ethylphenyl)-imidazolinium chloride; Cupric sulfate; potassium carbonate In N,N-dimethyl-formamide at 125℃; for 8h; Schlenk technique; Inert atmosphere; Sealed tube;
With dichloro(4,7-di(4',4''-difluoro-1',3',5',7'-tetramethyl-4'-bora-3'a,4'a-diaza-s-indacene)-1,10-phenanthroline)palladium(II); triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 25℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;
With anhydrous potassium acetate In dimethylsulfoxide-d6 at 100℃; 2.4. General procedure for the Sonogashira couplings General procedure: A two-necked flask was charged with, the aryl halide(0.180 mmol), 1,3,5-trimethoxybenzene (0.180 mmol, 30.3 mg) and KOAc (0.270 mmol, 26.5 mg). A dispersion of Fe3O4/oleic acid/Pd nanoparticles was made in DMSO-d6 (1.00 mL, 2.00 mg/mL) and was added to the two-necked flask. The acetylene (1.80 mmol) was added and the mixture was stirred for 3 h under reflux at 100 °C. After stirring, the nanoparticles were isolated from the mixture with a magnet. The conversion, with respect to the desired end product,was determined by 1H NMR of the crude reaction mixture, using 1,3,5-trimethoxybenzene as an internal standard.For more detailed information: see supplementary material.

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  • 4
  • [ 1849-25-8 ]
  • [ 98-88-4 ]
  • N-[4-(phenylethynyl)phenyl]-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane for 1h;
With triethylamine In dichloromethane for 0.166667h;
  • 5
  • [ 1849-25-8 ]
  • [ 4422-95-1 ]
  • N,N',N''-tris-[4-(phenylethynyl)phenyl]-1,3,5-benzenetricarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane for 0.166667h;
  • 6
  • [ 1849-25-8 ]
  • [ 99-63-8 ]
  • N,N'-bis-[4-(phenylethynyl)phenyl]-1,3-benzenedicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane for 0.166667h;
  • 7
  • [ 1849-25-8 ]
  • 4-phenylethynylbenzenediazonium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With nitrosonium tetrafluoroborate In acetonitrile at -30 - 0℃;
86% With nitrosonium tetrafluoroborate In acetonitrile at -30 - 0℃;
  • 8
  • [ 536-74-3 ]
  • [ 106-40-1 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
96% With potassium phosphate tribasic trihydrate; C50H40N6O2Pd(2+)*2F6P(1-); tetrabutylammomium bromide In 1,4-dioxane; water at 100℃; for 24h;
92% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;
92% With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 20℃; for 5h;
92% With tetrabutylammomium bromide; C44H68Cl4N12O4Pd2; caesium carbonate In ethanol; water at 80℃; for 10h;
91% With Cu[9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene]I; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 60℃; for 16h; Inert atmosphere; Typical Procedure for the Synthesis of Alkynylation Products General procedure: The mixture of aryl halides (1, 1.0 mmol) and alkynes (2, 1.2 mmol), Pd(OAc)2 (0.01mmol), Cu(Xantphos)I (0.01 mmol) and Cs2CO3 (2.0 mmol) in anhydrous DMF (5 mL) washeated at 60 oC for 16 h under argon atmosphere. After the reaction was finished, DMF was removed under reduced pressure. The mixture was extracted with ethyl acetate three times, then the combined organic layers were dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the pure product.
90% With Cu(II)IL/Schiff base complex decorated on γ-Fe2O3 In dimethyl sulfoxide at 90℃; for 5h; General procedure for Sonogashira cross-couplingreaction General procedure: In a typical run, 4-iodotoluene (1.0 mmol) and phenylacetylene(1.2 mmol) were dissolved in 2.0 mL DMSO.The catalyst (80 mg, 0.4 mol%) was added to the mixture,and the resultant mixture was stirred at 90 °C under aerobic conditions. The reaction progress was monitored byTLC. Upon the reaction completion, the magnetic catalystwas separated using an external magnetic field, and then,water (5 mL) and dichloromethane (5 mL) were addedto the reaction mixture. The organic layer was separated,and the aqueous layer was extracted with further DCM.The organic layers were combined, dried over MgSO4,andthen, the solvent was removed under reduced pressure. The products were purified by silica gel column chromatography.The products were identified by 1HNMR and 13CNMRand comparison with the corresponding authentic samples
90% With potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 0.7h; Sonogashira cross-coupling reaction General procedure: In general, in a 25-mL round-bottom flask, a mixture ofvarious aryl halide (1 mmol), phenylacetylene (0.122 g)(1.2 mmol), KOH (0.112 g) (2 mmol), catalyst PdSBA-Primine-furan (0.002 g) and dry DMF (4 mL) was refluxed forthe appropriate time as Table 3. The reaction progress waschecked using thin-layer chromatography (TLC), and thereaction mixture was diluted with water and then extractedwith chloroform. At the end of the reaction, the PdSBAPr-imine-furan catalyst was filtered-off, and the mixture wascooled-down to ambient temperature. The resulting residuewas purified by preparative chromatography using n-hexaneand ethyl acetate as (3:7) eluents. The chemical structureof the desired products was confirmed by GC-MS analysis(Table 1).
89% With triethylamine In neat (no solvent) at 90℃; for 2h; Schlenk technique;
89% With copper(l) iodide; C44H39N9O2Pd; triethylamine In dichloromethane at 20℃; for 8h;
88% With triethylamine In water for 2h; Heating; 2.4. Procedure for Sonogashira cross-coupling reaction General procedure: In a typical reaction, a mixture of alkyne (1.1 mmol), aryl halide(1.3 mmol), amine (2 mmol), catalyst (10 mg, 0.9 mol% of Pd)were added in water (4 mL) and stirred at 70 °C for required time.After completion of the reaction (monitored by GC-MS at differenttime intervals) it was cooled to room temperature and the catalystwas separated by simple centrifugal precipitation. The filtrated wasdiluted with water and extracted with 15 mL acetic acid. To obtainthe desired product the organic phase was washed with brine(2 x 10 mL) and dried over anhydrous Na2SO4, then filteredand evaporated under reduced pressure. The products were isolatedby silica gel column chromatography using hexane as eluent.The FT-IR and 1H NMR data of isolated products were comparedwith previously reported literature [26,27]. To check the reusabilityof the catalyst, the recovered catalyst was dried overnight at 100 °C and reused in a new coupling reaction under identical conditions.
86% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; ethanolamine In tetrahydrofuran at 60℃; for 12h;
84% With copper(l) iodide; C26H24N6NiS4; triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere; Typical procedure for the Sonogashira reaction of aryl bromides with phenylacetylene General procedure: In an oven-dried round bottom flask under an atmosphere of N2, a mixture of aryl halide (1 mmol), phenylacetylene (1.5 mmol), 1 (60.75 ppm or 0.05 mol%), copper(I) iodide (5 mmol), and Et3N (3.0 mmol) in DMF (5 mL) was taken. The reaction mixture was stirred 80 °C for 2 h. At the end of the mentioned time, the reaction mixture was diluted with EtOAc (20 mL), washed with water (3 x 10 mL). The combinedorganic layer was dried over anhydrous Na2SO4, filtered and stripped off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel using ethyl acetate and n-hexane mixtures to afford the desired product in high purity. The products were characterized by 1H and 13C NMR analysis. The procedure for the Sonogashira reaction of aryl bromides was similar as mentioned above in the case of aryl iodides, where aryl bromide (1 mmol) and 1 (121.5ppm or 0.1 mol %) were used and the reaction was carried out for 8 h.
80% With potassium carbonate In dimethyl sulfoxide at 110℃; for 6h;
78% With (Fe3O4 nanoparticles)(at)PEG/Cu-Co In water at 80℃; for 4.5h; Green chemistry;
76% With sodium hydroxide In water at 60℃; for 0.916667h; Green chemistry;
71% With N<SUP>2</SUP>,N<SUP>4</SUP>,N<SUP>6</SUP>-tridodecyl-1,3,5-triazine-2,4,6-triamine; potassium carbonate; palladium dichloride In water at 80℃;
69% With copper(l) iodide; (2,3,9,10,16,17,23,24-octakis(phenoxy)phthalocyaninato)palladium(II); N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 25℃; for 8h;
67% With C37H29ClN3PPdS; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; Typical procedure for the Sonogashira cross-coupling reaction General procedure: In an oven-dried round bottom flask, a mixture of aryl halide (1 mmol), phenylacetylene (1.5 mmol), complex 1 (0.5 mol % for aryl bromides, 1.0 mol % for aryl chlorides) and Et3N (3.0 mmol) in DMF (5 mL) was taken. The reaction mixture was stirred at room temperature (12 h for aryl bromides, 24 h for aryl chlorides). At the end of the time period mentioned, the reaction mixture was diluted with EtOAc (20 mL) and washed with water (3 x 10 mL). The organic layer was dried over anhydrous Na2SO4, filtered and stripped off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel using ethyl acetate and n-hexane mixtures to afford the desired product in high purity. The products were characterized by 1H and 13C NMR analysis.
66% With tetrabutylammomium bromide; sodium carbonate In water at 175℃; for 0.416667h; microwave irradiation;
55% With triethylamine In neat (no solvent) at 70℃; for 11h; A typical procedure for the Sonogashira-Hagihara cross-coupling reaction General procedure: A round-bottomed flask equipped with mechanical stirring was charged by a mixtureof phenylacetylene (1.2 mmol, 0.102 g), iodobenzene (1.0 mmol, 0.203 g), triethylamine(1 mmol, 0.101 g), and catalyst (0.007 g, 2.41 mol% Co), under solventfreeconditions at 70 °C. The progress of the reaction was monitored using TLC.After completion of the reaction (4 h), the mixture was diluted with ethyl acetate.Thereafter, the mesostructured catalyst was separated by simple filtration, washedwith EtOH (3 × 10 mL), and dried at 60 °C under vacuum overnight to remove theorganic residuals and solvents for use in the next run. The crude product was thenextracted with ethyl acetate, and the combined organic layer was dried over anhydrousNa2SO4.After solvent evaporation, the residue was purified by thin-layer chromatography using n-hexane/ethyl acetate (6:1) to afford white crystals of diphenylacetylene(0.174 g, 98% yield).
52% With triethylamine In toluene at 80℃; for 10h;
With potassium phosphate; C28H47ClN4P2Pd In 1,4-dioxane; ethylene glycol at 140℃; for 4h; Inert atmosphere;
With 1,4-diaza-bicyclo[2.2.2]octane; C29H35ClCoF6N7O6PPdS2 In acetonitrile at 90℃; for 4h; Inert atmosphere; Schlenk technique;

Reference: [1]Liu, Qing-Xiang; Cai, Kang-Qing; Zhao, Zhi-Xiang [RSC Advances, 2015, vol. 5, # 104, p. 85568 - 85578]
[2]Jadhav, Sanjay; Jagdale, Ashutosh; Kamble, Santosh; Kumbhar, Arjun; Salunkhe, Rajshri [RSC Advances, 2016, vol. 6, # 5, p. 3406 - 3420]
[3]Yadav, Deepika; Awasthi, Satish Kumar [New Journal of Chemistry, 2020, vol. 44, # 4, p. 1320 - 1325]
[4]Liu, Qingxiang; Zhang, Xiantao; Zhao, Zhixiang; Li, Xinying; Zhang, Wei [Chinese Journal of Chemistry, 2021, vol. 39, # 3, p. 605 - 613]
[5]Liu, Meilin; Ye, Mingyan; Xue, Yeye; Yin, Guodong; Wang, Dunjia; Huang, Jinkun [Tetrahedron Letters, 2016, vol. 57, # 29, p. 3137 - 3139]
[6]Nasseri, Mohammad Ali; Rezazadeh, Zinat; Kazemnejadi, Milad; Allahresani, Ali [Journal of the Iranian Chemical Society, 2019, vol. 16, # 12, p. 2693 - 2705]
[7]Mohajer, Fatemeh; Mohammadi Ziarani, Ghodsi; Badiei, Alireza [Journal of the Iranian Chemical Society, 2021, vol. 18, # 3, p. 589 - 601]
[8]Jadhav, Sanjay N.; Kumbhar, Arjun S.; Mali, Sawanta S.; Hong, Chang Kook; Salunkhe, Rajashri S. [New Journal of Chemistry, 2015, vol. 39, # 3, p. 2333 - 2341]
[9]Platonova, Yana B.; Tomilova, Larisa G.; Volov, Alexander N. [Journal of Catalysis, 2020, vol. 391, p. 224 - 228]
[10]Gogoi, Rajjyoti; Saikia, Rituraj; Borah, Geetika [Journal of Organometallic Chemistry, 2019, vol. 897, p. 80 - 88]
[11]Mohamed Ahmed, Mohamed S.; Mori, Atsunori [Tetrahedron, 2004, vol. 60, # 44, p. 9977 - 9982]
[12]Prabhu, Rupesh Narayana; Ramesh, Rengan [Tetrahedron Letters, 2016, vol. 57, # 44, p. 4893 - 4897]
[13]Ghabdian, Mahdieh; Nasseri, Mohammad A.; Allahresani, Ali; Motavallizadehkakhky, Alireza [Applied Organometallic Chemistry, 2018, vol. 32, # 12]
[14]Allahresani, Ali; Kazemnejadi, Milad; Nasseri, Mohammad Ali; Rezazadeh, Zinat [Dalton Transactions, 2020, vol. 49, # 30, p. 10645 - 10660]
[15]Nasseri, Mohammad Ali; Alavi, Seyyedeh Ameneh; Kazemnejadi, Milad; Allahresani, Ali [RSC Advances, 2019, vol. 9, # 36, p. 20749 - 20759]
[16]Iranpoor, Nasser; Rahimi, Sajjad; Panahi, Farhad [RSC Advances, 2015, vol. 5, # 61, p. 49559 - 49567]
[17]Platonova, Yana B.; Volov, Alexander N.; Tomilova, Larisa G. [Journal of Catalysis, 2019, vol. 373, p. 222 - 227]
[18]Prabhu, Rupesh Narayana; Pal, Samudranil [Tetrahedron Letters, 2015, vol. 56, # 37, p. 5252 - 5256]
[19]Appukkuttan, Prasad; Dehaen, Wim; Van Der Eycken, Erik [European Journal of Organic Chemistry, 2003, # 24, p. 4713 - 4716]
[20]Ghodsinia, Sara S. E.; Akhlaghinia, Batool; Jahanshahi, Roya [Research on Chemical Intermediates, 2021, vol. 47, # 8, p. 3217 - 3244]
[21]UlIslam, Rafique; Mahato, Sanjit K.; Shukla, Sudheesh K.; Witcomb, Michael J.; Mallick, Kaushik [ChemCatChem, 2013, vol. 5, # 8, p. 2453 - 2461]
[22]Location in patent: experimental part Bolliger, Jeanne L.; Frech, Christian M. [Advanced Synthesis and Catalysis, 2009, vol. 351, # 6, p. 891 - 902]
[23]Baweja, Saral; Clauss, Reike; Gelman, Dmitri; Hey-Hawkins, Evamarie [Dalton Transactions, 2022, vol. 51, # 4, p. 1344 - 1356]
  • 9
  • [ 1849-25-8 ]
  • 1-phenylethynyl-4-thiocyanatobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / NOBF4 / acetonitrile / -30 - 0 °C 2: 82 percent / KSCN / acetonitrile / 16 h
  • 10
  • [ 1849-25-8 ]
  • N-methyl-N-[4-(phenylethynyl)phenyl]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Et3N / CH2Cl2 / 0.17 h 2.1: NaH / dimethylformamide 2.2: dimethylformamide / 20 °C
  • 11
  • [ 26624-20-4 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol. KOH 2: phenylhydrazine
Multi-step reaction with 2 steps 1: KOH / methanol 2: Zn, aq. HCl
  • 12
  • [ 618-34-8 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: CuCl2*2H2O / aq. HCl 2: KOH / dioxane 3: Sn, aq. HCl / ethanol
  • 13
  • [ 1459-13-8 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: KOH / dioxane 2: Sn, aq. HCl / ethanol
  • 14
  • [ 100-05-0 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: CuCl2*2H2O / aq. HCl 2: KOH / dioxane 3: Sn, aq. HCl / ethanol
  • 15
  • [ 1694-20-8 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Br2 2: KOH / methanol 3: Zn, aq. HCl
  • 16
  • [ 1849-25-8 ]
  • nitrosonium tetrafluoroborate [ No CAS ]
  • 4-phenylethynylbenzenediazonium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.1% In acetonitrile GENERAL PROCEDURE FOR THE DLAZOTIZATION OF AROMATIC AMINES WITH NITROSONIUM TETRAFLUOROBORATE IN THE ACETONITRILE-SULFOLANE SYSTEM The nitrosonium salt was weighed out in a nitrogen filled dry box and placed in a round bottom flask equipped with a magnetic stirring bar and sealed with a septum. Acetonitrile and sulfolan were injected in 5 to 1 volume ratio and the resulting suspension was cooled in a dry ice-acetone bath TO-40°C. The solution of the aromatic amine was prepared by adding warm sulfolan (45-50°C) to the amine under a nitrogen blanket, sonication for 1 minute and subsequent addition of acetonitrile (10-20% by volume) and added to the nitrosonium salt suspension over 10 minutes. The reaction mixture was kept at-40°C for 30 minutes and let warm up to the room temperature. At this point the diazonium salt was precipitated by the addition of ether, collected by filtration, washed with ether and dried. Additional purification of the salt was accomplished by re-precipitation from DMSO by dichloromethane and/or etherFollowing the general diazotization procedure 4-phenylethynylaniline (0.579 g, 3.00 mmol) was treated with NOBF4 (0.368 g, 3.15 mmol) in pure acetonitrile (20 mL). For the synthesis of 4-phenylethynylaniline, please see Kosynkin et al. Org. Lett. 2001, vol. 3, pp. 993-995, incorporated herein by reference. Yellow needles of the desired product were precipitated with ether (0.753 g, 86.1% yield). IR (KBr) 3101,2294, 2217,1578, 1415,1033, 1071,845, 692 CM'H NMR (400 MHz, CD3CN) 8 8.86 (m, AA'part of AA'XX'pattern, J=8.7, 2.4, 1.7, 0.5 Hz, 2 H), 8.16 (m, XX'part OF AA'XX'PATTERN, J=8.7, 2.4, 1.7, 0.5 Hz, 2 H), 7.49-7. 59 (m, 3H), 7.67-7. 71 (m, 2H). 13C NMR (100 MHz, CD3CN) 8 137.15, 134.67, 134.06, 133.13, 131.45, 129.82, 121.96, 114.35, 101.58, 88.21
  • 17
  • [ 905447-69-0 ]
  • [ 1849-25-8 ]
  • [ 940902-59-0 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In 1-methyl-pyrrolidin-2-one at 55℃; for 16h; 3.A To a mixture of monoacid (4-7) (25 mg, 0.12 mmol) and HATU (68 mg, 0.18 mmol) in NMP (2 mL) was added amine building block (1.2 equivalents) and diisopropylethylamine (69 uL, 0.40 mmol). The reaction mixture was heated at 55° C. for 16 hours. LC-MS analysis of the reaction indicated that the reaction was complete. The volatiles were removed in vacuo, ethyl acetate was added, and the organic solution washed successively with saturated NaHCO3 (×1), water (×1), brine (×1), dried over magnesium sulfate and concentrated. Purification by Prep.LC afforded compounds 24 (80-90% yield).
  • 18
  • [ 1849-25-8 ]
  • (2R,3S)-3-(tertbutoxy)-2-(tert-butoxycarbonylamino)-butanoic acid [ No CAS ]
  • [ 905447-74-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In 1-methyl-pyrrolidin-2-one at 55℃; for 16h; 2.F.A To a mixture of Boc-D-Thr(t-Bu)-OH (100 mg, 0.36 mmol) and HATU (207 mg, 0.54 mmol) in NMP (2 mL) was added compound 9 (77 mg, 0.4 mmol) and diisopropylethylamine (209 uL, 1.2 mmol). The reaction mixture was heated at 55° C. for 16 hours. Ethyl acetate (5 mL) was added, and the organic solution washed successively with saturated NaHCO3 (×1), brine (×1), 0.5N HCl (×1), dried over magnesium sulfate and concentrated. Purification by flash column chromatography (SiO2, 20% ethyl acetate in hexanes) afforded compound 19 as a white solid. HPLC-MS tR=2.52 min (UV254 nm); mass calculated for formula C27H34N204 450.3, observed LCMS m/z 339.1 (M-(2×t-Bu)+H).
  • 19
  • [ 17702-41-9 ]
  • [ 1849-25-8 ]
  • [ 490041-00-4 ]
YieldReaction ConditionsOperation in experiment
27% With MeCN In benzene soln. decaborane. 4-phenylethynylaniline, and MeCN in benzene was refluxed under Ar for 3 days; solvent was removed under reduced pressure, residue was purified by chromy. on silica (hexane/EtOAc 3:1); elem. anal.;
  • 20
  • [ 13125-93-4 ]
  • [ 1849-25-8 ]
  • C20H13IN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With acetic acid In ethyl acetate at 40℃;
  • 21
  • [ 1942-30-9 ]
  • [ 1849-25-8 ]
  • 4-[(1Z)-2-phenylethenyl]benzeneamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 65% 2: 35% With 5% Au/Fe2O3; hydrogen In toluene at 60℃; for 1h; Autoclave; chemoselective reaction;
1: 54% 2: 30% With triethylsilane; chloro-trimethyl-silane; copper/silver activated zinc In tetrahydrofuran; methanol; water at 20℃; for 15h; stereoselective reaction; 4.3.9 Reduction of diaryl substituted alkynes General procedure: To a suspension of the Zn(Cu/Ag)-mixture (2.0 g) in MeOH/water (1:1, 6 mL), the alkyne (0.4 mmol, 1 equiv) in THF (0.3 mL) was added followed by the addition of Et3SiH (0.8 mmol, 2 equiv) and TMSCl (0.5 mL, 4.0 mmol, 10 equiv). The reaction mixture was stirred for the specified time for each reaction. Et2O (10 mL) was added, and the reaction mixture was filtered through a short plug of silica gel and eluted with Et2O (30 mL). The combined organic phases were washed with water (10 mL). The organic layer was separated and dried (MgSO4). The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (SiO2).
  • 22
  • [ 591-50-4 ]
  • [ 14235-81-5 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
96% With C16H20Cl2N2O2Pd; potassium hydroxide In water; acetonitrile at 20℃; for 3h; 31. General procedure for Sonogashira coupling reaction General procedure: In a 10 mL round bottom flask, the palladium complex (0.010 mmol) was dissolved in acetonitrile (2 mL). Aryl halide (1.0 mmol), alkyne (1.2 mmol), KOH (2.00 mmol) and distilled water (2 mL) were added. The mixture was stirred at room temperature (or 60° C) for the required time. After reaction completion, the product was extracted with ethyl acetate (3x5 mL). The combined organic layers were dried with anhydrous sodium sulfate. The product was analyzed with GC and GC-MS. The product was purified using column chromatography with hexane-ethyl acetate as eluent. The characterization data were in entire agreement with the previously reported literature.32-39
95% With dichlorido[2,2'-(4-methylbenzene-1,2-diyl)bis(4,4-dimethyl-4,5-dihydro-1,3-oxazole)-N,N']palladium(II); potassium hydroxide In water; acetonitrile at 20℃; for 3h; General procedure: Appropriate palladium complex was dissolved in acetonitrile. Aryl halide, alkyne, KOH and distilled water were added. The mixture was stirred at room temperature (or 60°C) for the required time.
93% With triethylamine In ethanol; water at 80℃; for 36h; Schlenk technique; Inert atmosphere; Green chemistry;
85% With iron(III) chloride; potassium phosphate; triphenylphosphine In toluene at 135℃; for 48h; Inert atmosphere;
78% With caesium carbonate In methanol at 65℃; for 24h;

  • 23
  • [ 605-65-2 ]
  • [ 1849-25-8 ]
  • [ 1233957-25-9 ]
YieldReaction ConditionsOperation in experiment
74 mg With pyridine at 20℃; Cooling with ice;
  • 24
  • [ 637-44-5 ]
  • [ 540-37-4 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
97% With copper(l) iodide; potassium carbonate; triphenylphosphine In water at 100℃; for 24h; Inert atmosphere; 4.2. General procedure for copper-catalyzed decarboxylative coupling of various aryl halides and alkynoic acids performed in water using PPh3 as the ligand General procedure: Aryl halide (0.5 mmol), alkynoic acid (0.6 mmol), CuI (2 mol %), PPh3 (4 mol %) and K2CO3 (1.0 mmol) were added to a screw-capped test tube. The tube was then evacuated and backfilled with argon (3 cycles). H2O (3 mL) was added by syringe at room temperature. The tube was again evacuated and backfilled with argon (3 cycles). The mixture was heated to 100 °C and stirred for 24 h. After cooling to room temperature, the mixture was diluted with water, and the combined aqueous phases were extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4 and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.
95% With copper(l) iodide; potassium carbonate; triphenylphosphine In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;
88% With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere;
  • 25
  • [ 2483-46-7 ]
  • [ 1849-25-8 ]
  • [ 1208242-21-0 ]
YieldReaction ConditionsOperation in experiment
46% With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane
  • 26
  • [ 1849-25-8 ]
  • (S)-2,6-diaminohexanoic acid [4-(phenylethynyl)phenyl]amide dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane 2: hydrogenchloride / tetrahydrofuran / 2 h
  • 27
  • [ 536-74-3 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 72 h / 20 °C 2: ferrous(II) sulfate heptahydrate / methanol; water / 11 h / Reflux
  • 28
  • [ 1262110-05-3 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
91 %Chromat. With sodium periodate In water; ethyl acetate at 20℃; for 0h;
  • 29
  • phenylethynyl(triphenylphosphine)gold(I) [ No CAS ]
  • [ 540-37-4 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
88% With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water at 20℃; for 12h;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran; acetonitrile at 60℃; for 2h; Inert atmosphere; 4.2. General conditions The gold reagent 1 (25 mmol), arylhalide (25 mmol), [PdCl2(PPh3)2] 1.0 ml of a 1.24 x 10-3 M stock solution in thf, 1.24 x 10-6 mol), CuI (0.5 ml of a 2.47 x 10-3 M stock solution in NCMe, 1.24 x 10-6 mol) were added successively to a vial, topped up to 5 ml with THF and sealed with a rubber septum or crimp-cap. The reactionwas stirred, and heated if indicated, and monitored by GC-MS. For reactions described in Table 3, 50 mmol of aryl iodide was employed. For the reactions described in Table 4, 25 mmol of iodobenzene was added initially. After 3 h of reaction at 35 °C, 25 mmol of the second aryl iodide was added, and the reaction allowed to proceed overnight before analysis.
  • 30
  • [ 1849-25-8 ]
  • [ 100-20-9 ]
  • [ 1228540-18-8 ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 0 - 20℃;
  • 31
  • [ 2170-06-1 ]
  • [ 540-37-4 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
87% With Potassium benzoate; triphenylphosphine; copper(l) chloride In 1,3-dimethyl-2-imidazolidinone at 120℃; for 12h; Inert atmosphere;
  • 32
  • [ 108-86-1 ]
  • [ 35283-05-7 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
48.3 mg In 1-methyl-pyrrolidin-2-one at 80℃; for 14h;
  • 33
  • [ 106-40-1 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl; bis(η3-allyl-μ-chloropalladium(II)); tetra-n-butylammoniumfluoride trihydrate / 1-methyl-pyrrolidin-2-one; water / 16 h / 50 °C / Inert atmosphere 2: 1-methyl-pyrrolidin-2-one / 14 h / 80 °C
  • 34
  • [ 1942-30-9 ]
  • [ 1694-20-8 ]
  • [ 6624-53-9 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
With diiron nonacarbonyl; tributylphosphine; Triethoxysilane In tetrahydrofuran at 60℃; for 48h; Inert atmosphere; optical yield given as %de; chemoselective reaction;
  • 35
  • [ 536-74-3 ]
  • [ 1694-20-8 ]
  • [ 6624-53-9 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; triphenylphosphine / water 2: diiron nonacarbonyl; tributylphosphine; Triethoxysilane / tetrahydrofuran / 48 h / 60 °C / Inert atmosphere
  • 36
  • [ 2170-06-1 ]
  • [ 106-40-1 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
65% With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; benzyltri(n-butyl)ammonium chloride; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 40℃; for 22h; Inert atmosphere;
  • 37
  • [ 1849-25-8 ]
  • [ 4309-66-4 ]
YieldReaction ConditionsOperation in experiment
93% With methanol; borane-ammonia complex; C16H29Cl2CoN2P at 50℃; for 16h; Inert atmosphere; Schlenk technique; chemoselective reaction;
92% Stage #1: 4-phenylethynylphenylamine With FeH(CO)(NO)(PPh3)2; phenylsilane; triethylamine In tetrahydrofuran at 40℃; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;
92% With diphenylsilane; water; C32H48Cl2Co2N6O2; sodium triethylborohydride In tetrahydrofuran at 30℃; for 12h; stereoselective reaction;
86% With water; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 130℃; for 12h; Schlenk technique; stereoselective reaction;
86% With potassium ethyl xanthogenate In water; N,N-dimethyl-formamide at 130℃; for 12h; 15 Example 15: Synthesis of (E)-6-styrylquinoline Take a 25 ml reaction tube, add 193 mg of 4-phenylethynylaniline, 320 mg of potassium ethylxanthate, 36 μl of water, 2 ml of N,N-dimethylformamide, and stir the reaction at 130°C for 12h At the end of the reaction, add 10 mL of ethyl acetate to quench the reaction, wash with 10 mL of saturated brine, separate the organic phase, and extract the aqueous phase 3 times with ethyl acetate (10 ml*3). Combine the organic phase and add anhydrous sulfuric acid After drying with sodium, the solvent was distilled off under reduced pressure, and then separated by column chromatography to obtain 166 mg of (E)-4-styrylaniline with a yield of 86%.
82% With manganese; water; palladium diacetate; magnesium acetate In N,N-dimethyl-formamide at 80℃; for 24h; Schlenk technique; Inert atmosphere; diastereoselective reaction;
82% Stage #1: 4-phenylethynylphenylamine With nickel(II) iodide; 1,1'-bis-(diphenylphosphino)ferrocene In 1,4-dioxane at 20℃; for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogen In 1,4-dioxane at 100℃; for 18h; Autoclave;
81% With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; C19H13I2N3O2Ru; hydrogen In water at 80℃; for 7h; Autoclave; Schlenk technique; chemoselective reaction;
61 mg With borane-ammonia complex In acetonitrile at 50℃; for 15h; Inert atmosphere; Schlenk technique; stereoselective reaction;

  • 38
  • [ 1849-25-8 ]
  • (E)-1-(4-acetamidophenyl)-2-phenylethene [ No CAS ]
  • [ 429689-40-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: FeH(CO)(NO)(PPh3)2; phenylsilane; triethylamine / tetrahydrofuran / 40 °C 2.2: 2 h / 0 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: copper(l) iodide; zinc; tris(triphenylphosphine)ruthenium(II) chloride / 1,4-dioxane; water / 16 h / 100 °C / Schlenk technique; Inert atmosphere
  • 39
  • [ 1849-25-8 ]
  • cis-para-Aminostilbene [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With copper; ethylene glycol; potassium hydroxide at 150℃; for 0.5h; Sonication; Microwave irradiation; Green chemistry; stereoselective reaction;
91% With hydrogen In acetonitrile at 110℃; for 15h; chemoselective reaction;
89% Stage #1: 1-amino-4-(phenylethynyl)benzene With FeH(CO)(NO)(PPh3)2; methyl-phenyl-vinyl-silane; triethylamine In tetrahydrofuran at 60℃; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol at 130℃; for 0.166667h; Inert atmosphere; Microwave irradiation; optical yield given as %de; diastereoselective reaction;
86% With methanol; borane-ammonia complex; C15H18Br2CoN3O(1-)*H(1+) at 27℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; diastereoselective reaction;
76% With iron; hydrogen; acetonitrile; 1-n-butyl-2,3-dimethylimidazolium bistrifluoromethylsulfonylamide In n-heptane at 80℃; for 18h; diastereoselective reaction;

  • 40
  • [ 1849-25-8 ]
  • [ 429689-40-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: FeH(CO)(NO)(PPh3)2; methyl-phenyl-vinyl-silane; triethylamine / tetrahydrofuran / 60 °C 2.2: 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation
  • 41
  • [ 1849-25-8 ]
  • [ 75-36-5 ]
  • N-(4-(2-phenylethynyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium carbonate In tetrahydrofuran at -78 - 20℃; for 1h;
93% With triethylamine In dichloromethane at 0 - 20℃;
93% With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Schlenk technique;
86% With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere; Schlenk technique;

  • 42
  • (Z)-2,2'-dibromostilbene [ No CAS ]
  • [ 1849-25-8 ]
  • [ 1414856-47-5 ]
YieldReaction ConditionsOperation in experiment
62% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 120℃; for 10h; Schlenk technique; Inert atmosphere; 3) Typical Procedures General procedure: A Schlenk tube was charged with dibromides (0.3 mmol), Pd2dba3(0.0075 mmol), DPEPhos (0.03 mmol), and Cs2CO3 (0.75 mmol). The tube was evacuated and backfilled with argon before amine (0.36 mmol) and 2 mL toluene was added. The reaction mixture was stirred at 120 oC for 8-24h. After the reaction mixture was diluted with EtOAc and washed with water and brine, the solution was dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 50:1 petroleum ether/ethyl acetate) to provide the desired product.
  • 43
  • [ 540-37-4 ]
  • [ 159087-45-3 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
88% With 1,3-dimethyl-2-imidazolidinone; potassium carbonate; triphenylphosphine; copper(l) chloride at 120℃; for 12h;
  • 44
  • [ 1849-25-8 ]
  • [ 1431105-88-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 1 h / 25 °C / Inert atmosphere 2: sodium peroxoborate tetrahydrate / acetic acid / 10 h / 60 °C / Inert atmosphere
  • 45
  • [ 1849-25-8 ]
  • [ 1431105-97-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 5 h / 80 °C / Inert atmosphere 2: tert.-butylnitrite / tetrahydrofuran / 1 h / 60 °C / Inert atmosphere
  • 46
  • [ 1849-25-8 ]
  • [ 1431105-99-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetonitrile / 5 h / 80 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / acetonitrile / 10 °C 2.2: 0.67 h / 10 - 25 °C
  • 47
  • [ 1849-25-8 ]
  • [ 1431106-02-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetonitrile / 1 h / 25 °C / Inert atmosphere 2.1: sodium nitrite; sulfuric acid / water / 1 h / 0 °C 2.2: 3 h / 0 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; benzene / 12 h / 90 °C / Inert atmosphere
  • 48
  • [ 1849-25-8 ]
  • [ 1431106-05-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetonitrile / 1 h / 25 °C / Inert atmosphere 2.1: sodium nitrite; sulfuric acid / water / 1 h / 0 °C 2.2: 3 h / 0 °C 3.1: trifuran-2-yl-phosphane; copper(l) iodide; palladium dichloride; N-ethyl-N,N-diisopropylamine / toluene / 3 h / 50 °C / Inert atmosphere; Schlenk technique
  • 49
  • [ 1849-25-8 ]
  • [ 1431106-07-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: acetonitrile / 1 h / 25 °C / Inert atmosphere 2.1: sodium nitrite; sulfuric acid / water / 1 h / 0 °C 2.2: 3 h / 0 °C 3.1: trifuran-2-yl-phosphane; copper(l) iodide; palladium dichloride; N-ethyl-N,N-diisopropylamine / toluene / 3 h / 50 °C / Inert atmosphere; Schlenk technique 4.1: acetonitrile / 1 h / 25 °C / Inert atmosphere
  • 50
  • [ 1849-25-8 ]
  • [ 187796-85-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetonitrile / 1 h / 25 °C / Inert atmosphere 2.1: sodium nitrite; sulfuric acid / water / 1 h / 0 °C 2.2: 18 h / 0 - 25 °C
  • 51
  • [ 1849-25-8 ]
  • [ 1431105-86-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetonitrile / 1 h / 25 °C / Inert atmosphere 2.1: sodium nitrite; sulfuric acid / water / 1 h / 0 °C 2.2: 3 h / 0 °C
  • 52
  • [ 1849-25-8 ]
  • [ 670-54-2 ]
  • [ 1391453-86-3 ]
YieldReaction ConditionsOperation in experiment
78% In acetonitrile at 25℃; for 1h; Inert atmosphere;
  • 53
  • [ 1849-25-8 ]
  • [ 1518-16-7 ]
  • [ 1431105-83-7 ]
YieldReaction ConditionsOperation in experiment
85% In acetonitrile at 80℃; for 5h; Inert atmosphere;
  • 54
  • [ 1849-25-8 ]
  • [ 479-33-4 ]
  • [ 1426925-96-3 ]
YieldReaction ConditionsOperation in experiment
60% In diphenylether Inert atmosphere; Reflux;
  • 55
  • [ 636-98-6 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc; tris(triphenylphosphine)ruthenium(II) chloride; potassium hydroxide / 1,4-dioxane; water / 16 h / 80 °C / Schlenk technique; Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere; Schlenk technique
  • 56
  • [ 1849-25-8 ]
  • [ 4309-66-4 ]
  • 4-[(1Z)-2-phenylethenyl]benzeneamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.333 % de With copper(l) iodide; tris(triphenylphosphine)ruthenium(II) chloride; zinc In 1,4-dioxane; water at 100℃; for 16h; Schlenk technique; Inert atmosphere; Overall yield = 90 %; Overall yield = 87.9 mg; chemoselective reaction;
81.818 % de With copper(l) iodide; tris(triphenylphosphine)ruthenium(II) chloride; zinc In 1,4-dioxane; water at 100℃; for 36h; Schlenk technique; Inert atmosphere; Overall yield = 97 %; Overall yield = 94.7 mg; chemoselective reaction;
60 % de With methanol; borane-ammonia complex; C20H45Cl2CoNP2 at 50℃; for 20h; Overall yield = 67 %; Overall yield = 65 mg; chemoselective reaction;
80 % de With [([Ru(diphenylphosphido)2])IrH(acetonitrile)3][BF4]2; hydrogen In ethanol at 70℃; for 15h; Schlenk technique; Overall yield = 95 %Spectr.; stereoselective reaction;
88.235 % de With ethanol; potassium <i>tert</i>-butylate; 1,3-bis(mesityl)imidazolium chloride; bis(pinacol)diborane; copper(l) chloride at 25℃; for 5h; Inert atmosphere; Schlenk technique; Overall yield = 62 %; Overall yield = 24.3 mg; stereoselective reaction;
80 % de With methanol; water; cobalt(II) iodide; zinc at 60℃; Inert atmosphere; Schlenk technique; Overall yield = 78 %; stereoselective reaction;
52 % de With water; 1,2-bis-(diphenylphosphino)ethane; cobalt(II) iodide; zinc In acetonitrile at 60℃; Inert atmosphere; Schlenk technique; Overall yield = 73 %; stereoselective reaction;
64.557 % de With dichlorotetrakis(dimethylsulfoxide)ruthenium(II); potassium <i>tert</i>-butylate; isopropyl alcohol In toluene at 100℃; for 24h; Sealed tube; Inert atmosphere; Overall yield = 51 percent; Overall yield = 30 mg;
85.714 % de With diphenylsilane; water; C32H48Cl2Co2N6O2; sodium triethylborohydride In tetrahydrofuran at 30℃; for 12h; Overall yield = 79percent; stereoselective reaction;
With methanol; potassium borohydride; fac-[Mn((1,2-bis(di-isopropylphosphino)ethane))(CO)3(CH2CH2CH3)] at 90℃; for 20h; Overall yield = 89 percent;

Reference: [1]Schabel, Tobias; Belger, Christian; Plietker, Bernd [Organic Letters, 2013, vol. 15, # 11, p. 2858 - 2861]
[2]Schabel, Tobias; Belger, Christian; Plietker, Bernd [Organic Letters, 2013, vol. 15, # 11, p. 2858 - 2861]
[3]Fu, Shaomin; Chen, Nan-Yu; Liu, Xufang; Shao, Zhihui; Luo, Shu-Ping; Liu, Qiang [Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8588 - 8594]
[4]Takemoto, Shin; Kitamura, Manami; Saruwatari, Shuhei; Isono, Atsutaka; Takada, Yoko; Nishimori, Rie; Tsujiwaki, Mina; Sakaue, Naoki; Matsuzaka, Hiroyuki [Dalton Transactions, 2019, vol. 48, # 4, p. 1161 - 1165]
[5]Bao, Hanyang; Zhou, Bingwei; Jin, Hongwei; Liu, Yunkui [Journal of Organic Chemistry, 2019, vol. 84, # 6, p. 3579 - 3589]
[6]Li, Kangkui; Khan, Ruhima; Zhang, Xuexin; Gao, Yang; Zhou, Yongyun; Tan, Heng; Chen, Jingchao; Fan, Baomin [Chemical Communications, 2019, vol. 55, # 39, p. 5663 - 5666]
[7]Li, Kangkui; Khan, Ruhima; Zhang, Xuexin; Gao, Yang; Zhou, Yongyun; Tan, Heng; Chen, Jingchao; Fan, Baomin [Chemical Communications, 2019, vol. 55, # 39, p. 5663 - 5666]
[8]Ekebergh, Andreas; Begon, Romain; Kann, Nina [Journal of Organic Chemistry, 2020, vol. 85, # 5, p. 2966 - 2975]
[9]Chen, Ke; Zhu, Hongdan; Li, Yuling; Peng, Qian; Guo, Yinlong; Wang, Xiaoming [ACS Catalysis, 2021, vol. 11, # 21, p. 13696 - 13705]
[10]Farrar-Tobar, Ronald A.; Weber, Stefan; Csendes, Zita; Ammaturo, Antonio; Fleissner, Sarah; Hoffmann, Helmuth; Veiros, Luis F.; Kirchner, Karl [ACS Catalysis, 2022, vol. 12, # 4, p. 2253 - 2260]
  • 57
  • [ 1849-25-8 ]
  • (E)-1-(4-acetamidophenyl)-2-phenylethene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: copper(l) iodide; zinc; tris(triphenylphosphine)ruthenium(II) chloride / 1,4-dioxane; water / 36 h / 100 °C / Schlenk technique; Inert atmosphere
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 5.5 h / 20 °C 2: [{Ir(H)((rac)-BINAP)}2(μ-Cl)3]Cl; hydrogen / 1,4-dioxane / 16 h / 80 °C / 750.08 Torr
  • 58
  • [ 1849-25-8 ]
  • [ 124-40-3 ]
  • [ 149-73-5 ]
  • [ 1374425-85-0 ]
YieldReaction ConditionsOperation in experiment
0.06 g Stage #1: 4-phenylethynylphenylamine; trimethyl orthoformate With toluene-4-sulfonic acid for 12h; Reflux; Stage #2: dimethyl amine In dichloromethane; water at 25℃; for 16h; 6 Production of N,N-dimethyl-N′-[4-(phenyl-1-ethynyl)phenyl]formamidine (Compound 5) Methyl orthoformate (6.32 g) and 0.05 g of p-toluenesulfonic acid monohydrate were added to 0.50 g of the 4-(2-phenyl-1-ethynyl)aniline (Compound 4-1) produced in Production Example 1, and the mixture was heated under reflux for 12 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was dissolved in 200 ml of dichloromethane. A 50% dimethylamine aqueous solution (0.47 g) was added thereto, and the mixture was stirred at 25° C. for 16 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), thereby obtaining 0.06 g of N,N-dimethyl-N′-[(4-(phenyl-1-ethynyl)phenyl]formamidine (Compound 5).
  • 59
  • [ 1849-25-8 ]
  • [ 1454818-90-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / toluene / 16 h / 120 °C 2: (acetonitrile)(tris(2,4-di-tert-butylphenyl)phosphite)gold(I) hexafluoroantimonate / m-xylene / 48 h / 120 °C / Schlenk technique; Inert atmosphere
  • 60
  • [ 110-52-1 ]
  • [ 1849-25-8 ]
  • [ 1454818-87-1 ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine In toluene at 120℃; for 16h;
  • 61
  • [ 615-43-0 ]
  • [ 1849-25-8 ]
  • [ 1507357-30-3 ]
  • [ 1507357-31-4 ]
YieldReaction ConditionsOperation in experiment
1: 21% 2: 39% With tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere; regioselective reaction;
1: 6% 2: 14% With palladium diacetate; sodium carbonate; triphenylphosphine; lithium chloride In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;
With tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 24h;
  • 62
  • [ 1849-25-8 ]
  • C30H35ClO3 [ No CAS ]
  • N-(4-(phenylethynyl)phenyl)-16-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6a,7,12,12a,13,14,14a-pentadecahydro-2H-(6,12b-etheno)benzo[b]chrysene-7,12-dione-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
204 mg With triethylamine In toluene at 75 - 80℃; Inert atmosphere; General procedure of syntheses of amides 4 General procedure: mixture of 16-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6a,7,12,12a,13,14,14a-pentadecahydro-2H-(6,12b-etheno)benzo[b]chrysene-7,12-dione-1-carboxylic acid 1 (500 mg, 1.0 mmol) and oxalyl chloride (0.3 mL, 4.3 mmol) in of dry dichloromethane (10 mL) was stirred in argon for 3.5 h at room temperature. The solventwas evaporated at a reduced pressure. This crude product 2 without further purification wasdissolved in of toluene (10 mL) and added to mixture Et3N (0.25 mL) and amine 3 (1.1 mmol) inof toluene (5 ml). A mixture was stirred for 1-4 h at 75-80 C under the argon atmosphere. The solvent was evaporated at a reduced pressure, the product 4 was purified by chromatography on Al2O3 (elution with dichloromethane and mixture ethyl acetate - toluene) and crystallized from hexane
  • 63
  • [ 92669-44-8 ]
  • [ 1849-25-8 ]
  • [RuIV(5,10,15,20-tetramesitylporphyrinato(2-))(NH{4-(phenylethynyl)phenyl})2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In ethanol for 8h;
  • 64
  • [ 94764-62-2 ]
  • [ 1849-25-8 ]
  • C26H18N2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In acetone Reflux; Synthesis of N-(4-phenylethynylaniline)-N'-(1-naphthoyl)thiourea (PAT) Treatment of the latter with an equimolar amount of PHE in acetone produced N-(4-phenylethynylaniline)-N'-(1-naphthoyl)thiourea (PAT) as the targeted product. The product was then recrystallised from acetonitrile, yielding the yellow crystalline solid of PAT (70% yield) in a needle-like shape. 1H NMR (400.11 MHz, CDCl3): δ 7.38-7.39 (m, 3H, C6H5); 7.56-7.77 (m, 7H, naphthoyl); 7.88 (pseudo-d, JHH = 7 Hz, 2H, C6H4); 8.09 (pseudo-d, JHH = 8 Hz, 2H, C6H4); 8.11 (pseudo-d, JHH = 8 Hz, 1H, C6H4); 8.43 (pseudo-d, JHH = 8 Hz, 1H, C6H4); 9.10, 12.78 (2 * s, 1H, NH); 13C NMR (100.61 MHz, CDCl3): δ 88.8, 90.0 (2 * s, 2 * C≡C); 121.6, 123.1, 123.4, 124.5, 126.4, 127.1, 128.3, 130.6, 131.6, 132.2, 133.3, 133.8, 137.4 (18 * s, Ar); 169.2 (s, C=O); 177.8 (s, C=S); Elemental analysis for C27H17N3S: [Found (Calcd.)]: C = 77.13 (76.82); H = 4.30 (4.46); N = 7.17 (6.89); S = 8.13 (7.89).
  • 65
  • [ 106-47-8 ]
  • [ 536-74-3 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
96% With sulphonic acid functionalized porphyrin meso-substituted triazolium anchored ionic liquid at 20℃; for 24h; Irradiation;
90% With palladium; potassium carbonate In ethanol; water at 90℃; for 10h;
84% With cetyltrimethylammonim bromide; potassium carbonate; sodium L-ascorbate In water at 80℃; for 48h; Inert atmosphere; Schlenk technique;
80% With copper(l) iodide; C48H48N8Pd; sodium t-butanolate at 20℃; for 8h;
78% With potassium phosphate tribasic trihydrate; C50H40N6O2Pd(2+)*2F6P(1-); tetrabutylammomium bromide In 1,4-dioxane; water at 100℃; for 30h;
55% With triethylamine In neat (no solvent) at 70℃; for 15h; A typical procedure for the Sonogashira-Hagihara cross-coupling reaction General procedure: A round-bottomed flask equipped with mechanical stirring was charged by a mixtureof phenylacetylene (1.2 mmol, 0.102 g), iodobenzene (1.0 mmol, 0.203 g), triethylamine(1 mmol, 0.101 g), and catalyst (0.007 g, 2.41 mol% Co), under solventfreeconditions at 70 °C. The progress of the reaction was monitored using TLC.After completion of the reaction (4 h), the mixture was diluted with ethyl acetate.Thereafter, the mesostructured catalyst was separated by simple filtration, washedwith EtOH (3 × 10 mL), and dried at 60 °C under vacuum overnight to remove theorganic residuals and solvents for use in the next run. The crude product was thenextracted with ethyl acetate, and the combined organic layer was dried over anhydrousNa2SO4.After solvent evaporation, the residue was purified by thin-layer chromatography using n-hexane/ethyl acetate (6:1) to afford white crystals of diphenylacetylene(0.174 g, 98% yield).
50% With potassium carbonate In ethanol; water at 20℃; for 6h; Irradiation;
38% With [(Pd{(κ2-C,N)-(3-(dimethylaminomethyl)indole)}µ-OAc)2]; potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 7h; General procedure for the Sonogashira reaction General procedure: A 50-mL round-bottom flask was charged with aryl halide (1 mmol), phenylacetylene (1.5 mmol), K2CO3 (2 mmol), DMF:H2O (1:1) (4 mL), and the C,N-palladacycle (0.1 mol% Pd). The mixture was stirred at 100°C for the desired reaction time. The reaction was monitored by GC. After the reaction was complete, the mixture was cooled to room temperature and diluted with EtOAc and H2O. The product was extracted with EtOAc and the organic phase dried over MgSO4, filtered, and concentrated. The arylalkynes obtained could be purified by silica gel column chromatography (hexane:EtOAc).The arylalkyne products were known compounds and were characterized from their 1H NMR and 13C NMR.
With potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 6h; 2.5. General procedure for the Sonogashira cross-coupling reaction General procedure: An aryl halide (1 mmol) and phenylacetylene (1.5 mmol)were added to a mixture of Fe3O4/oleic acid/Pd catalyst (0.005mmol) and K2CO3 (2 mmol) in ethanol (6 mL) as solvent in aglass flask under vigorous stirring. The mixture was refluxed at75 °C for 6 h under aerobic conditions. The palladium catalystwas recovered by a simple magnet and reused for the next run.The solution was washed with ethanol and deionized water (10mL) and dried in a vacuum oven at 60 °C.
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 8h;

  • 66
  • [ 1849-25-8 ]
  • [ 14678-71-8 ]
  • C40H29N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In diphenylether for 24h; Reflux; Inert atmosphere;
  • 67
  • [ 695-99-8 ]
  • [ 1849-25-8 ]
  • [ 536-74-3 ]
  • 2-chloro-4-(2-phenyl-5-(phenylethynyl)-1H-indol-3-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 4-phenylethynylphenylamine; phenylacetylene With copper(l) chloride In methanol Inert atmosphere; Stage #2: 2-Chloro-1,4-benzoquinone In methanol at 25 - 28℃; for 12h; Irradiation; Inert atmosphere; regioselective reaction;
  • 68
  • [ 106-47-8 ]
  • [ 637-44-5 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
83% With bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 24h;
  • 69
  • [ 1849-25-8 ]
  • [ 108-24-7 ]
  • N-(4-(2-phenylethynyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With triethylamine In dichloromethane at 20℃; for 5.5h;
  • 70
  • [ 1849-25-8 ]
  • [ 132993-24-9 ]
  • 1-nitro-N-[4-(phenylethynyl)phenyl]naphthalen-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene for 16h; Reflux; Inert atmosphere; 72.1 (1) 1-Nitro-N-[4-(phenylethynyl)phenyl]naphthalen-2-amine [0221] 1-Nitro-2-naphthyl trifluoromethanesulfonate (733 mg, 2.28 mmol), 4-(phenylethynyl)aniline (440 mg, 2.28mmol), palladium(II) acetate (51 mg, 0.028 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene triphenylphosphine(264 mg, 0.456 mmol), and potassium carbonate (473 mg, 3.42 mmol) were dissolved in dry toluene (10 mL), and thesolution was refluxed by heating for 16 hours under a nitrogen atmosphere. The reaction mixture was left to cool, andthen the insoluble matter was separated by filtration, and washed away with ethyl acetate. The organic layer was washedwith saturated aqueous sodium hydrogencarbonate, and dried over anhydrous sodium sulfate. The solvent was evaporatedunder reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate= 4/1) to obtain the title compound (830 mg, yield 100%).1 H NMR (CDCl3, 400 MHz) δ: 7.2-7.3 (2H, m), 7.3-7.4 (3H, m), 7.43 (2H, d, J=8Hz), 7.5-7.6 (4H, m), 7.64 (1H, t, J=9Hz),7.74 (1H, d, J=8Hz), 7.80 (1H, d, J=9Hz), 8.48 (1H, d, J=9Hz), 9.37 (1H, s)
  • 71
  • [ 1849-25-8 ]
  • C30H13N3O6 [ No CAS ]
  • C44H22N4O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-phenylethynylphenylamine; C30H13N3O6 In N,N-dimethyl acetamide at 20℃; for 9h; Stage #2: With pyridine; acetic anhydride In N,N-dimethyl acetamide at 110℃; for 4.5h; 3.1.3 2.04 g of D was added to 7 ml of DMAc, and after the complete dissolution of D, a solution of 3-phenylacetylene aniline in DMAc (the molar ratio of intermediate 2 to 3-phenylacetylene aniline was added to solution D at room temperature 1: 1.1, Vdmac = (total solid mass (g) * 3.3) ml) and allowed to react at room temperature for 9 h. (D: acetic anhydride: pyridine molar ratio of 1: 6: 6) was added to the reaction solution, and the temperature was raised to 110 ° C for 4.5 h after completion of the addition. The filter cake is treated by methanol stirring, suction filtration, filter cake dissolving in acetone, adding activated carbon to decolorize, filtering to remove activated carbon, filtering cake And dried in vacuo to give the desired product.
  • 72
  • [ 1849-25-8 ]
  • [ 1942-30-9 ]
  • 1-nitroso-4-(phenylethynyl)benzene [ No CAS ]
  • (Z)-1,2-bis[4-(phenylethynyl)phenyl]diazene 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 19% 2: 27% 3: 12% With Oxone; silver nitrate In water; acetonitrile at 60℃; for 1h;
  • 73
  • [ 1420804-57-4 ]
  • [ 1849-25-8 ]
  • 4-(4-bromophenyl)-1-[4-(phenylethynyl)phenyl]piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: C11H15BrO2 With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In acetonitrile at -30℃; for 1h; Inert atmosphere; Stage #2: 4-phenylethynylphenylamine With N-ethyl-N,N-diisopropylamine In acetonitrile at -30 - 23℃; for 19h; Inert atmosphere;
  • 74
  • [ 1849-25-8 ]
  • 4-(4-iodophenyl)-1-[4-(phenylethynyl)phenyl]piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / -30 °C / Inert atmosphere 1.2: 19 h / -30 - 23 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: 0.33 h / 23 °C / Inert atmosphere
  • 75
  • [ 1849-25-8 ]
  • 2-{4-[4-(4-bromophenyl)piperidin-1-yl]phenyl}-3-phenylbuta-1,3-diene-1,1,4,4-tetracarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / -30 °C / Inert atmosphere 1.2: 19 h / -30 - 23 °C / Inert atmosphere 2.1: acetonitrile / 1 h / 23 °C / Inert atmosphere
  • 76
  • [ 1849-25-8 ]
  • (2-{4-[4-(4-bromophenyl)piperidin-1-yl]phenyl}-2-[4-(dicyanomethylene)-2,5-cyclohexadien-1-ylidene]-1-phenylethylidene)malononitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / -30 °C / Inert atmosphere 1.2: 19 h / -30 - 23 °C / Inert atmosphere 2.1: dichloromethane / 1 h / 84 °C / Inert atmosphere
  • 77
  • [ 1849-25-8 ]
  • [ 4559-70-0 ]
  • 1,2,3-triphenylbenzo[b]phosphole P-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With magnesium(II) nitrate hexahydrate; di-tert-butyl peroxide In 1,4-dioxane at 100℃; for 12h; Sealed tube; regioselective reaction;
  • 78
  • [ 1849-25-8 ]
  • [ 31029-96-6 ]
YieldReaction ConditionsOperation in experiment
100% With 2-chloropyridine-N-oxide; iodine In acetonitrile at 80℃; for 14h; Sealed tube; chemoselective reaction;
  • 79
  • [ 536-74-3 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride In tetrahydrofuran Schlenk technique; Inert atmosphere;
  • 80
  • [ 1849-25-8 ]
  • C56H36NP [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water / 1 h / 5 °C 1.2: 1 h / 65 °C 1.3: 1 h / 5 °C 2.1: diethyl ether / 10 h / Inert atmosphere; Reflux
  • 81
  • [ 1849-25-8 ]
  • C32H24NP [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water / 1 h / 5 °C 1.2: 1 h / 65 °C 1.3: 1 h / 5 °C 2.1: diethyl ether / 10 h / Inert atmosphere; Reflux
  • 82
  • [ 1849-25-8 ]
  • 1-(4-azidophenyl)-2-phenylacetylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-phenylethynylphenylamine With hydrogenchloride In water at 5℃; for 1h; Stage #2: With sodium nitrite In water at 65℃; for 1h; Stage #3: With sodium azide In water at 5℃; for 1h; 1.1-1.3; 3.1-3.3 Referring to Figure 2, the method for synthesizing the tetraphenylphosphorylated phosphine derivative of the present embodiment comprises the following steps: (1) To 19.3 g of the compound a1 (), 1 L of 5% hydrochloric acid was added, and the reaction temperature was controlled at 5 ° C.Stir for 1 h;(2) adding 10 mL of a 10% sodium nitrite aqueous solution to the above reaction solution,The reaction temperature is controlled at 5 ° C.Stir for 1 h;(3) adding 8% aqueous sodium azide solution to the above reaction solution, 100 mL,The reaction temperature is controlled at 5 ° C.Stir for 1 h; extract, wash, dry, filter, remove the solvent, column chromatography to obtain compound b1,This compound b1 is the first intermediate of the present invention.
  • 83
  • [ 1849-25-8 ]
  • [ 103-80-0 ]
  • 2-phenyl-N-(4-(phenylethynyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% In dichloromethane Inert atmosphere;
  • 84
  • [ 1849-25-8 ]
  • [ 103-80-0 ]
  • 2-phenyl-N-(4-(phenylethynyl)phenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / Inert atmosphere 2: potassium <i>tert</i>-butylate; dimethylamine borane / 0.5 h / 120 °C / Inert atmosphere
  • 85
  • [ 144382-01-4 ]
  • [ 536-74-3 ]
  • [ 1849-25-8 ]
YieldReaction ConditionsOperation in experiment
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 25℃; for 2h; Inert atmosphere; Sealed tube; General procedure for the Sonogashira coupling reactions between diorganyl tellurides RTeR and phenyl acetylene General procedure: A mixture of diorganyl telluride RTeR (1 mmol), phenyl acetylene, 2a (0.26 g, 2.5 mmol), Pd(dppf)Cl2 (0.07 g, 0.1 mmol), K2CO3 (0.41 g, 3 mmol) and CuI (0.23 g, 1.2 mmol) in DMSO (3 mL) was stirred at room temperature under N2 for 2 h. The progress of the reaction was monitored by TLC. After the completion of reaction, the dark precipitate formed was filtered off. The reaction mixture was diluted with CH2Cl2 (20 mL) and the organic layer was washed with water (4*10 mL), dried over anhyd. Na2SO4, and concentrated under vacuum. The crude product was purified by silica column chromatography.
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