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Product Details of [ 2789-88-0 ]

CAS No. :2789-88-0 MDL No. :MFCD00010651
Formula : C16H14 Boiling Point : -
Linear Structure Formula :- InChI Key :OFDOCXDLDQXWIX-UHFFFAOYSA-N
M.W : 206.28 Pubchem ID :520354
Synonyms :

Safety of [ 2789-88-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 2789-88-0 ]

* 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 [ 2789-88-0 ]

[ 2789-88-0 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 2789-88-0 ]
  • [ 2510-76-1 ]
YieldReaction ConditionsOperation in experiment
85.8% With sodium benzoate; 4,4'-Dimethoxy-2,2'-bipyridin; bis(pinacol)diborane; nickel(I) bromide; In water; N,N-dimethyl-formamide; at 80℃; for 12h;Inert atmosphere; Weigh nickel bromide (3.3mg, 10mol%), 4,4'-dimethoxy-2,2'-bipyridine (7.2mg, 22mol%),1,2-Di-p-toluene acetylene (31mg, 1.0equiv.),Sodium benzoate (43.2mg, 2.0equiv.),bis(pinacolato)diboron(114.3mg, 3.0equiv.) was added to a 25mL reaction tube with a branch,Then replace the air in the reaction tube with argon,Add distilled water (8.1 microliters, 3.0 equiv.), DMF (2ml) with a micro syringe under argon conditions,The reaction tube was sealed and reacted at 80C for 12 hours.After the reaction stopped, the reaction system was washed with water,Spin the reaction solution to dryness,The Z-alkene product is obtained by column chromatography,The total yield of the reaction is quantitative (85.8%), the ratio of cis-trans olefins in the product: Z/E=93/7.
80% With tetra-(n-butyl)ammonium iodide; dimethyl amine; palladium dichloride; In methanol; at 60℃; for 3.5h;Electrochemical reaction; Electrochemical hydrogenation was carried out in three-necked round-bottomed flask (10 mL), with a graphite rod anode and a platinum disc cathode. 1 (0.80 mmol), PdCl2 (0.5 mol%, 0.7 mg), Me2NH (0.5 equiv, 0.2 mL, 2.0 M in the methonal), "Bu4NI (1.0 equiv, 295.5 mg) and MeOH (8.0 mL) were placed in a three-necked round-bottomed flask at 60 C with a constant current of 0.1 A maintained for 2.5-5 h. The mixture was cooled to room temperature, and diluted with 20 mL of EtOAc. The organic mixture was then washed with brine, dried over anh. Na2SO4, and evaporated under vacuum. The residue was purified by flash column chromatography (n- hexane) on silica gel to provide the desired products 2.
60% With quinoline; hydrogen; at 50℃; under 7500.75 Torr; for 16h;Autoclave; The added AuNPore (5.0mg, 5mol%)In the autoclave of the catalyst,Quinoline (5 mL) was added,Substrate 1,2-bis (4-methylphenyl) acetylene (103.14 mg, 0.5 mmol)Hydrogen (1.0 MPa),Placed in a magnetic stirrer at 50 C for 16 h,Column chromatography (silica gel,200-300 mesh; development agent,Petroleum ether) to give 62.5 mg of (Z) -1,2-bis (4-methylphenyl)Yield 60%.
With [(PPh3)CuCl]4; hydrogen; lithium tert-butoxide; In isopropyl alcohol; toluene; at 100℃; under 3800.26 Torr; for 3h;Schlenk technique; Autoclave; General procedure: In a glove box, to a vial, [(PPh3)CuCl]4 (7.2 mg, 5.0 μmol),toluene (1.0 mL), LiOtBu (40 mg, 0.50 mmol) and iPrOH (60 mg, 1.0 mmol) were added in thisorder. After the resulting mixture was stirred for 1 min at room temperature, 1a (160 mg, 1.0 mmol)and toluene (2.0 mL) were added. The vial was placed in an autoclave and the autoclave was takenout of the glove box. N2 in the autoclave was replaced with H2 by positive pressure of H2. Then, themixture was stirred at 100 C for 3 h under 5 atm of H2. After cooling to room temperature, H2 wasreleased and the mixture was diluted with EtOAc. The conversion was determined by GC analysiswith n-tridecane (18 mg, 0.10 mmol) as an internal standard. The resulting solution was filteredthrough a pad of silica gel and the yields of the products were determined by 1H NMR analysis with1,3,5-trimethoxybenzene as an internal standard.

  • 2
  • [ 2789-88-0 ]
  • [ 3457-48-5 ]
YieldReaction ConditionsOperation in experiment
95% With ammonium iodide; potassium ethyl xanthogenate; In water; dimethyl sulfoxide; at 130℃; for 12h;Schlenk technique; General procedure: A mixture of 1,2-diphenylethyne (1.0 mmol) and EtOCS2K (1.2 mmol) and NH4I (2.0 mmol) in 3 mL of DMSO/H2O (2:1) were stirred for 12 hours at 130 oC. Monitoring with TLC and GC-MS analysis was used to show the starting materials were completely consumed. After the reaction was finished, the reaction mixture was cooled to room temperature, the solution was filtered though a small amount of silica gel. The residue was purified by silica gel preparative TLC (n-hexane: EtOAc = 20:1), which furnished benzyl as a pale-yellow solid
95% With ammonium iodide; potassium ethyl xanthogenate; In water; dimethyl sulfoxide; at 130℃; for 12h; In the reaction tube, 1,0-Di-m-toluene acetylene 103 mmg (0.50 mmol) and ethyl xanthate potassium 96 mmg (0.60 mmol) were added, respectively. Ammonium iodide 145 mmg (1.00 mmol), dimethyl sulfoxide 2 mL, and water 1 mL. The reaction was stirred at 130 C for 12 hours. At the end of the reaction, 10 mL of ethyl acetate was added to quench the reaction, and 5 mL of saturated brine was added to wash, and the organic phase was separated.The aqueous phase was extracted three times with ethyl acetate (5 mL of ethyl acetate each time) and the organic phase was combined and dried over anhydrous sodium sulfate.The solvent was distilled off under reduced pressure,The target product 1,2-di-m-toluene-ethylidene-1,2-dione was obtained by column chromatography to give a yield of 95%.
92% With 2-chloropyridine-N-oxide; mercuric triflate; In acetonitrile; at 23℃; for 3h; General procedure: Representative procedure: To a solution of 1a (1 mmol) and 2-Cl-pyridine N-oxide(2.1 mmol) in CH3CN (5 mL) was added Hg(OTf)2 (0.1 mmol) and the mixture wasstirred at 23 C for 3 h. The solvent was evaporated and the residue was purified byflash column chromatography (hexane/EtOAc 20:1) to give the product 2a in 95%yield
78% General procedure: In an oven-dried Schlenk tube (25 mL) equipped with a magnetic stir bar was charged with Cu(OAc)2 (10 mol%), Cy-JohnPhos (25 mol%), LiOBut (0.24 mmol), (Bpin)2 (0.3 mmol) and alkyne (1) (0.2 mmol, if the alkyne is solid). The tube was evacuated and backfilled with N2. To this Schlenk tube were added DMF (0.6 mL), 1,4-dioxane (0.9 mL), H2O (0.2 mmol) and alkynes 1 (0.2 mmol, if the alkyne is liquid) by syringe. After stirring for 20 min at room temperature under nitrogen atmosphere, the reaction mixture was flushed with O2. The Schlenk tube was sealed, and the reaction mixture was allowed to stir at room temperature for 48 h. After quenched with aqueous NH4Cl, the aqueous layer was extracted three times with EtOAc. The combined organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the product (2) (silica gel, EtOAc-PE). The products obtained herein are known compounds, and spectral properties are consistent with literature values
69% With C25H21ClN5Pd(1+)*Cl(1-); silver nitrate; In 1,4-dioxane; water; at 90℃; for 48h; General procedure: To a solution of 1,2-diphenylethyne (5a) (500mg, 2.808mmol) in 1,4-dioxane, water (20mL:5mL v/v), complex 3a (63mg, 0.112mmol, 4mol%), AgNO3 (38mg, 0.224mmol, 8mol%) were added and the reaction mixture was stirred at 90C, the progress of the reaction was monitored by TLC. After 19h the reaction mixture was cooled to room temperature, diluted with water and extracted with CH2Cl2. The separated organic layer was dried over Na2SO4, concentrated under vacuum. The residue was subjected to silica gel column chromatography by using hexane/EtOAc (9:1, v/v) as eluent to give benzil (6a) (551mg, 2.623mmol) as a yellow solid in 93% yield. Similarly to a solution of 5b (1000mg, 4.48mmol) in 1,4-dioxane, water (40mL:10mL v/v), complex 3a (102mg, 0.179mmol, 61mg, 4mol%), AgNO3 (61mg, 0.358mmol, 8mol%) were added and the reaction mixture was stirred at 90Cfor 28h to give 6b (871mg, 3.415mmol) as a yellow solid in 76% yield. The characterization data for all the 1,2-diketones (6a-l) are given in the supporting information

  • 3
  • [ 2789-88-0 ]
  • [ 84907-55-1 ]
YieldReaction ConditionsOperation in experiment
(i) NBS, (PhCO)2O2, CCl4, (ii) hexamethylenetetramine, CHCl3, (iii) aq. AcOH; Multistep reaction;
  • 4
  • [ 106-38-7 ]
  • [ 766-97-2 ]
  • [ 2789-88-0 ]
YieldReaction ConditionsOperation in experiment
85% With palladium diacetate; potassium carbonate; urea; In ethanol; at 60℃; for 6h; 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.
85% With palladium diacetate; In ethanol; at 60℃; for 8h;Green chemistry; 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.
80% With triethylamine; In water; for 2h;Heating; 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.
70% With N,N,N',N'-tetramethylguanidine; In water; for 15h; General procedure: A mixture of aryl iodide (1.0mmol), phenylacetylene (1.2mmol), TMG (2.0mmol), water (2mL) and 0.01mmol (20mg) of Pd complex 4 was stirred at 80C temperature for a desired reaction time. Further, the reaction mixture was extracted with ethyl acetate and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using hexane as the eluent to give the corresponding coupling products.

  • 5
  • [ 2749-93-1 ]
  • [ 2789-88-0 ]
YieldReaction ConditionsOperation in experiment
96% With [PhC≡W{OC(CF3)Me2}3]; In toluene; at 25℃; for 2h;Inert atmosphere; Molecular sieve; Glovebox; General procedure: Under an argon atmosphere, a flask was charged with the substrate (0.5 mmol), molecular sieves 5 Å (500 mg) and toluene (internal alkynes: 2.5 mL, terminal alkynes: 24 mL). Then the catalyst (0.5 mol % W2F3, 1 mol % WPhF3) was added and the mixture was stirred for 2 h at room temperature. The catalyst and the molecular sieves were removed by filtration through alumina and the solvent was evaporated. The crude reaction product was purified by flash chromatography on silica gel with ethyl acetate-hexane (1:8).
  • 6
  • [ 624-31-7 ]
  • [ 1066-54-2 ]
  • [ 2789-88-0 ]
YieldReaction ConditionsOperation in experiment
90% General procedure: 4-Iodoanisole (1mmol), TMSA (1.1mmol) and K2CO3 (2mmol) were added to a freshly prepared solution of PdNPs (5mL) in a 25mL round bottomed flask fitted with stopper. Then, the reaction mixture was stirred at 40C. The reaction progress was monitored by TLC, until complete consumption of aryl iodide. To the reaction mixture containing in situ formed 4-ethynylanisole the next batch of aryliodide (1mmol) was added and the reaction mixture was further allowed to stir until complete consumption of the arylacetylene. In this manner the targeted unsymmetrical diarylacetylene was formed. The detailed procedure is provided in the Supp. Info. Detailed procedure for synthesis of symmetrical diarylacetylenes is also mentioned in SI.
  • 7
  • [ 624-31-7 ]
  • [ 766-97-2 ]
  • [ 2789-88-0 ]
YieldReaction ConditionsOperation in experiment
97% With palladium diacetate; potassium carbonate; urea; In ethanol; at 20℃; for 3h; 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.
96% With palladium diacetate; In ethanol; at 60℃; for 2h;Green chemistry; 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.
95% With 3,4,5-trihydroxybenzoic acid; palladium diacetate; caesium carbonate; In ethanol; at 40℃; for 4h;Green chemistry; General procedure: In a 50 mL round bottom flask, a mixture of aryl halide (0.5 mmol), terminal alkyne (0.65 mmol), Pd(OAc)2 (1 mol%), gallic acid (1 mol%) and K2CO3 (1.5 mmol) in 4 mL EtOH was stirred at 40 C. After completion (vide TLC); the reaction mixture was diluted with H2O and extracted with ethyl acetate (3 × 10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluent: Hexane) to give corresponding functionalized alkyne. Purity of isolated product was confirmed by comparing 1H, 13C NMR data with authentic compounds.
93% With pyrrolidine; In water; at 45℃; for 20h;Green chemistry; General procedure: A mixture of the aryl halide (2 mmol), Pd(II)-AOFs (0.10 g, 0.5 mol/%), pyrrolidine (8 mmol), phenylacetylene (2.4 mmol), in H2O (15 mL) was heated in an oil bath at 45 C for 20 h under stirring. The catalyst was separated from the reaction system by simple filtration, and washed sequentially with ethyl acetate, hot ethanol and water, and reused in the next reaction. The filtrate was extracted with 60-90 C petroleum ether and the extaract was dried. The solvent was then removed by rotary evaporation to give a crude product. The crude products was purified by column chromatography purification on H 60 silica powder using 60-90 C petroleum ether. They were characterised by melting point and NMR spectroscopy. bis(p-Tolyl)acetylene (i): M.p. 136-139 C (lit.30 138-140 C) 1H NMR (300 MHz, CDCl3): δ 7.40 (d, J=4.8 Hz, 4H), 7.14 (d, J=4.8 Hz, 4H), 2.35 (s, 6H).
90% With triethylamine; In neat (no solvent); at 20℃; for 6h; General procedure: A mixture of aryl iodide (1.0mmol), phenylacetylene (1.2mmol), Et3N (2.0mmol) and 0.005mmol (10mg) of Pd(II) complex 4 was stirred at room temperature for a desired reaction time. Further, the reaction mixture was extracted with ethyl acetate and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using hexane as eluent to give the corresponding coupling products.
90% With triethylamine; In water; for 2h;Heating; 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.
89% With triethylamine; In N,N-dimethyl-formamide; at 90℃; for 4h; General procedure: Aryl halide (1 mmol), terminal alkyne (1.2 mmol), triethylamine (2 mmol) and h-Fe3O4mTiO2-NH2-Pd (20 mg) were added to 3 ml DMF and the reaction mixture wasstirred at 90C for the appropriate time. After completion of the reaction, the reactionmixture was cooled to room temperature and diluted with hot ethanol (10 ml). After that,the catalyst was separated by an external magnet from the cooled mixture, washed withacetone, dried in an oven and re-used for a consecutive run under the same reaction conditions.The filtrate was concentrated and the resulting residue was purified by short columnchromatography on silica gel to afford the desired product.
87% With triethylamine; In N,N-dimethyl-formamide; for 3.5h;Heating; Green chemistry; General procedure: Aryl halide (1 mmol), terminal alkyne (1.2 mmol), triethylamine (2 mmol) and Fe3O4(at)SiO2-T/Pd (20 mg) were added to 3 mL DMF as solvent and the reaction mixture was stirred at 90 C for the appropriate time. After completion of the reaction, the reaction mixture was cooled and diluted with hot ethanol (10 mL). Then, the catalyst was separated by an external magnet from the cooled mixture, washed with acetone, dried in an oven and re-used for a consecutive run under the same reaction conditions. The filtrate was concentrated and the resulting residue was purified by short column chromatography on silica gel to afford the desired product in excellent yield [40].
85% With potassium carbonate; In ethanol; at 80℃; for 12h;Aerobic conditions; General procedure: Iodobenzene (204 mg, 1 mmol), phenylacetylene (102 mg, 1 mmol), K2CO3 (276 mg, 2 equiv, 2 mmol) and Pd-MCM-48 (25 mg) were mixed in 5 mL of ethanol and refluxed for 12 h with stirring. The reaction progress was monitored by TLC. The reaction mixture was cooled to room temperature, and solvent was removed under vacuum. The residue was extracted with 100 mL of ethyl acetate and organic layer was washed with water (2×5 mL). The organic layer was dried over Na2SO4, and solvent was evaporated to provide diphenylacetylene as a white solid (151 mg, 85%). The 1H NMR and 13C NMR spectroscopic data of the product were in good agreement with previously reported data.2f This procedure was followed for all the reactions listed in Table 3. All the products listed in Table 3 are known and all of the products gave 1H and 13C NMR data consistent with the structures and data in the literature. The reference for each compound is provided in Table 3.
84% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; A 30-mL round-bottom flask was charged with 4-iodotoluene (870 mg, 4.0 mmol),PdCl2(PPh3)2 (140 mg, 0.20 mmol), CuI (76 mg, 0.40 mmol), degassed NEt3 (0.84 mL,6.0 mmol), and THF (5 mL). 4-Ethynyltoluene (0.61 mL, 4.8 mmol) was added dropwise,and the resulting suspension was stirred at room temperature. After 2 h, the mixture wasconcentrated under reduced pressure. After an addition of aqueous HCl (1 M, 10 mL), themixture was extracted with CH2Cl2 (10 mL × 3). The combined organic layer was washedwith brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Theresidue was purified by column chromatography on silica gel with hexane as an eluent togive 1b (696 mg, 3.4 mmol, 84%) as a white solid.
81% With C38H35ClCuN4P; potassium carbonate; In toluene; at 110 - 120℃; for 20h;Inert atmosphere; General procedure: In a round bottom flask, 8 mol% of catalyst, K2CO3 (2.0 mmol),phenylacetylene (2.5 mmol), aryl halide (2.0 mmol), and 20 mltoluene was taken. The whole solution was heated with stirring at110-120 C for 20 h under N2 atmosphere. The solutionwas cooledto room temperature and filtered to remove insoluble impurities.Filtrate was evaporated and the solid was then passed throughcolumn. The desired compound was characterized by 1H NMR and13C NMR.
65% With palladium diacetate; potassium carbonate; 4-amino-benzoic acid; In ethanol; at 20℃; for 4h; General procedure: A round bottom flask was charged with aryl halide (0.5 mmol) and terminal acetylene (0.6 mmol). To the mixture, Pd(OAc)2 (1 mol%), A4 (2 mol%) andK2CO3 (1.5 mmol) were added. The reaction mixture was stirred at roomtemperature in EtOH (4 mL) for the mentioned time. The formation of theproduct was confirmed by monitoring the TLC. The reaction mixture was thenextracted with ethyl acetate (3 10 mL). The extracted layer was dried overNa2SO4 and concentrated in rotary evaporator. The crude product was purifiedby column chromatography over silica gel (Eluent: n-hexane) to obtain thedesired product. The pure products were confirmed by 1H and 13C NMR.
With sodium acetate; In dimethyl sulfoxide; at 120℃; General procedure: Iodobenzene (0.50mmol), phenylacetylene (0.55mmol), NaOAc (1mmol), and dimethyl sulfoxide (DMSO, 8mL) were mixed. Well-dispersed Pd/Fe3O4GO (0.4mol%) in DMSO (2mL) was added to the mixture with vigorous stirring. After the reaction, the catalyst was separated from the solution by centrifugation. The product was extracted three times with dichloromethane (20mL) and dried using MgSO4.
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃;Schlenk technique; Inert atmosphere; General procedure: Chapter one: A 100 mL schlenk tube was charged with iodobenzene (3.0 mmol), ethynyltrimethylsilane (3.6 mmol), PdCl2(PPh3)2 (0.15 mmol), CuI (0.15 mmol), Et3N:THF = 3:2 (10.0 mL). Then the tube was charged with nitrogen, and was stirred at room temperature for the indicated time until complete consumption of starting material as monitored by TLC analysis. After the completion of the reaction, then the reaction mxtuire was filtered and the filtrate diluted in ethyl acetate and washed with water. The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The crude product was purified by silica gel column chromatography (petroleum ether unless otherwise noted) to give the corresponding trimethyl(phenylethynyl)silanes, and used for the next reaction.

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[53]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10386 - 10391
[54]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9186 - 9189
[55]Catalysis Communications,2015,vol. 72,p. 150 - 155
[56]Organic Letters,2017,vol. 19,p. 6498 - 6501
[57]Angewandte Chemie - International Edition,2018,vol. 57,p. 8316 - 8320
    Angew. Chem.,2018,vol. 130,p. 8449 - 8453,5
[58]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3171 - 3175
[59]Advanced Synthesis and Catalysis,2019,vol. 361,p. 683 - 689
[60]Organic Letters,2019,vol. 21,p. 921 - 925
[61]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4386 - 4392
[62]Organic and Biomolecular Chemistry,2019,vol. 17,p. 7679 - 7683
[63]Journal of the American Chemical Society,2019,vol. 141,p. 18970 - 18976
[64]Chemical Communications,2020,vol. 56,p. 2614 - 2617
[65]Organic and Biomolecular Chemistry,2020,vol. 18,p. 3158 - 3163
[66]Chemical Communications,2020,vol. 56,p. 4408 - 4411
[67]Organic Letters,2020,vol. 22,p. 3765 - 3769
[68]Synthesis,2020,vol. 52,p. 1223 - 1230
[69]Advanced Synthesis and Catalysis,2020,vol. 362,p. 5627 - 5631
[70]Organic and Biomolecular Chemistry,2021,vol. 19,p. 561 - 567
[71]Organic Letters,2021,vol. 23,p. 6589 - 6593
  • 8
  • [ 106-43-4 ]
  • [ 115-19-5 ]
  • [ 2789-88-0 ]
YieldReaction ConditionsOperation in experiment
69% With tetrabutylammomium bromide; potassium carbonate; palladium dichloride; XPhos; In water; at 120℃; for 24h;Inert atmosphere; Schlenk technique; Green chemistry; General procedure: To a 25-mL Schlenk tube equipped with magnetic stir bar, aryl chloride (0.4 mmol), 2-methyl-3-butyn-2-ol (0.6 mmol), K2CO3 (2.0 equiv.), TBAB (1.0 equiv.), PdCl2 (2 mol%), and Xphos (4 mol%) were added in turn, then 2 mL H2O was added, and then the solution was refluxed for 24 h under N2 atmosphere. After the reaction was complete, the mixture was extracted with EtOAc or CH2Cl2. The combined organic layer was dried with anhydrous Na2SO4 and evaporated in vacuum. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluent to afford the desired product.
  • 10
  • [ 1530-37-6 ]
  • [ 2789-88-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 39.6 percent / LiOMe / methanol 2: pyridinium hydrobromide perbromide / acetic acid / 1.5 h / Ambient temperature 3: 56 percent / KOH, HO(CH2CH2O)3H / 0.08 h / 160 °C
  • 11
  • [ 26305-75-9 ]
  • [ 2789-88-0 ]
  • [ 33320-28-4 ]
  • [ 939044-79-8 ]
  • 12
  • [ 67-56-1 ]
  • [ 2789-88-0 ]
  • [ 99-75-2 ]
  • 13
  • [ 872217-44-2 ]
  • [ 1295-35-8 ]
  • [ 2789-88-0 ]
  • [ 1035697-00-7 ]
  • 14
  • [ 1295-35-8 ]
  • [ 1035697-07-4 ]
  • [ 2789-88-0 ]
  • [ 1036028-51-9 ]
  • [ 1036028-51-9 ]
  • 15
  • [ 2789-88-0 ]
  • [ 1126-00-7 ]
  • [ 1037289-14-7 ]
YieldReaction ConditionsOperation in experiment
79% With 1,2,3,4-tetraphenylcyclopentadiene; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 80℃; for 6h;
79% With 1,2,3,4-tetraphenylcyclopentadiene; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; regioselective reaction;
  • 16
  • [ 91-40-7 ]
  • [ 2789-88-0 ]
  • [ 1147303-97-6 ]
  • 17
  • [ 91-40-7 ]
  • [ 2789-88-0 ]
  • [ 1147304-29-7 ]
  • [ 1147303-97-6 ]
  • 18
  • [ 2789-88-0 ]
  • [ 13909-34-7 ]
  • C29H27NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With bis(1,5-cyclooctadiene)nickel(0); trimethylaluminum; tricyclohexylphosphine In hexane; toluene at 20℃; for 6.5h; Inert atmosphere;
  • 20
  • [ 2789-88-0 ]
  • [ 596-38-3 ]
  • [ 1241954-77-7 ]
YieldReaction ConditionsOperation in experiment
72% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,2,3,4-tetraphenylcyclopentadiene; copper(II) acetate monohydrate In o-xylene Inert atmosphere; Heating;
  • 21
  • [ 591-50-4 ]
  • [ 2789-88-0 ]
  • [ 98-80-6 ]
  • [ 70592-06-2 ]
YieldReaction ConditionsOperation in experiment
66% With [(OCH2CMe2CH2O)P-S-Pd(PPh3)]2; potassium carbonate In water at 100℃; for 0.5h;
  • 22
  • [ 5720-05-8 ]
  • [ 766-97-2 ]
  • [ 2789-88-0 ]
YieldReaction ConditionsOperation in experiment
95% With C32H26FeIN2PPd; potassium acetate; silver(l) oxide; In dichloromethane; at 25℃; for 24h; General procedure: A mixture of arylboronic acids (0.5 mmol), alkynes(0.6 mmol), the prescribed amount of catalysts, Ag2O(0.5 mmol), and KOAc (0.75 mmol) in 1,2-dichloroethane(DCE) (3 mL) under air was stirred at 80 or 25Cfor24 h. After being cooled, the mixture wasfiltered. The solvent was removed under reduced pressure. The resultingresidue was purified byflash chromatography on silica gelto afford the desired coupled products, which were characterized by comparing their m.p. and1HNMRspectra.
  • 24
  • [ 2789-88-0 ]
  • [ 1864-94-4 ]
  • C23H20O2 [ No CAS ]
  • 25
  • [ 624-31-7 ]
  • [ 471-25-0 ]
  • [ 2789-88-0 ]
  • [ 22666-07-5 ]
YieldReaction ConditionsOperation in experiment
8%Chromat.; 89% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane; In dimethyl sulfoxide; at 30 - 80℃; for 9h;Darkness; Aerobic condition; General procedure: Aryl iodide (2.0 mmol), propiolic acid (168.1 mg, 2.4 mmol) Pd(PPh3)2Cl2 (70.2 mg, 0.1 mmol), 1,4-bis(diphenylphosphino)butane (85.3 mg, 0.2 mmol), CuI (38.1 mg, 0.2 mmol), DBU (730.8 mg, 4.8 mmol) and K2CO3 (331.7 mg, 2.4 mmol) were combined with DMSO (4.0 mL) in a small round-bottomed flask. The resulting reaction mixture was stirred under aerobic and dark conditions at 30 C for 6 h and subsequently at 80 C for 3 h. The solvent was removed from the reaction mixture under the vacuum. The crude mixture was dissolved with Et2O (15 mL), washed with brine (15 mL × 3), dried over MgSO4, and filtered. The combined solvent was removed under vacuum, and the resulting crude product was purified by flash chromatography on silica gel.
  • 26
  • [ 2789-88-0 ]
  • [ 676578-20-4 ]
  • [ 1284216-15-4 ]
  • 27
  • [ 2789-88-0 ]
  • [ 265671-00-9 ]
  • [ 1313886-30-4 ]
YieldReaction ConditionsOperation in experiment
73% With tributyl-amine; tris-(o-tolyl)phosphine; palladium dichloride; In N,N-dimethyl-formamide; at 90℃; for 18h;Inert atmosphere; General procedure: A solution of compound 1 (0.25 mmol), alkyne (0.75 mmol), PdCl2 (3.3 mg, 0.02 mmol), P(o-Tolyl)3 (11.4 mg, 0.04 mmol), and nBu3N (119 μL, 0.50 mmol) in DMF (5 mL) was stirred at 90 C until 1 was consumed as monitored by TLC. The reaction mixture was allowed to cool to room temperature. The solvent was evaporated and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate/dichloromethane 10-5:1:1) to afford corresponding cinnoline.
  • 28
  • [ 2789-88-0 ]
  • [ 5216-31-9 ]
  • [ 1611-83-2 ]
  • [ 1309763-17-4 ]
  • [ 1309763-16-3 ]
  • 29
  • [ 2789-88-0 ]
  • [ 1611-83-2 ]
  • [ 1309763-17-4 ]
  • 30
  • [ 88070-48-8 ]
  • [ 2789-88-0 ]
  • 2-methyl-3,4-di-p-tolylisoquinolin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium iodide dihydrate; palladium 10% on activated carbon; potassium acetate; caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 36h;Schlenk technique; General procedure: A mixture of a substituted benzamide (1) (0.3 mmol, 1.0 equiv),an alkyne (2) (0.6 mmol or 0.9 mmol, 2.0 equiv or 3.0 equiv),10% Pd/C (0.03 mmol, 10 mol%, Alfa Aesar, No. 044696, eggshell,reduced), NaI·2H2O (0.6 mmol, 2.0 equiv), Cs2CO3 (0.3 mmol, 1.0equiv), and KOAc (0.6 mmol, 2.0 equiv) was weighted in a Schlenktube equipped with a stir bar. DMF (1.0 mL) was added and themixture was stirred at 120 C for 36 h under air. Afterwards, themixture was filtered and washed with H2O (30 mL) and extractedwith CH2Cl2 (3×30 mL). The combined organic phase was driedwith anhydrous Na2SO4. After removal of solvents under reducedpressure, the residue was absorbed to small amounts of silica. Thepurification was performed by flash column chromatography onsilica gel with EA:PE (Petroleum ether) = 1:5 or 1:10 as eluent.
  • 31
  • [ 2789-88-0 ]
  • [ 588-16-9 ]
  • [ 1332835-82-1 ]
YieldReaction ConditionsOperation in experiment
78% With palladium diacetate; copper(II) bis(trifluoromethanesulfonate); silver(l) oxide; In N,N-dimethyl acetamide; at 120℃; for 4h;Inert atmosphere; General procedure: To a Schlenk tube were added N-aryl amide (0.4 mmol, 1.0 equiv.), alkyne (0.6 mmol, 1.5 equiv.), Pd(OAc)2 (10 mol%), Ag2O (1.5 equiv.), Cu(OTf)2 (1.0 equiv.) and DMA (3.0 mL) successively under N2. The mixture was stirred at room temperature for a few min. Then the tube was placed in a pre-heated (120 oC) oil and stirred as monitored by TLC. The solution was then cooled to rt, diluted with ethyl ether (30 mL), washed with H2O (10 mL), dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel with petroleum ether/ ethyl acetate as eluent. It was eluted by petroleum ether and then the ratio of eluent was from 75/1 to50/1.
  • 32
  • [ 91-01-0 ]
  • [ 2789-88-0 ]
  • [ 1332624-99-3 ]
YieldReaction ConditionsOperation in experiment
97% With silver hexafluoroantimonate; acetic acid; In 1,2-dichloro-ethane; at 80℃; for 1h;Inert atmosphere; General procedure: A mixture of diphenylmethanol (1a) (0.3 mmol, 55 mg), diphenylacetylene (2a) (0.6 mmol,107 mg), AgSbF6 (0.2 mmol, 14 mg), AcOH (1 mmol, 60 mg), and 1-methylnaphthalene (ca. 50 mg)as an internal standard was stirred in 1,2-dichloroethane (2.5 mL) under Ar at 80 oC for 1 h. Then theresulting mixture was diluted by ethyl acetate (30 mL). The organic layer was washed by water (30 mL,two times) and brine (30 mL) and dried over Na2SO4. After removal of the solvents under vacuum,product 3aa (90 mg, 87%) was isolated by column chromatography on silica gel using hexane-ethylacetate as eluent. Further purification by GPC (gel permeation chromatography) was performed, ifneeded.
  • 33
  • [ 624-31-7 ]
  • [ 75-20-7 ]
  • [ 2789-88-0 ]
YieldReaction ConditionsOperation in experiment
99% With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: A 100 mL round bottom flask with a magnetic stir bar was charged with copper iodide (0.1 equiv), palladium acetate (0.05 equiv), and triphenylphosphine (0.1 equiv) in acetonitrile. The solution was degassed with nitrogen for 20 min. Then, triethylamine (3 equiv), aryl iodides (1 equiv), and calcium carbide (3 equiv) were added. The mixture was stirred at room temperature overnight under nitrogen atmosphere. The reaction mixture was then filtrated through a short plug of silica gel and washed with hexane. The filtrate was evaporated under vacuum to give the desired compound.
  • 34
  • [ 29488-24-2 ]
  • [ 2789-88-0 ]
  • [ 1332494-87-7 ]
  • 35
  • [ 2789-88-0 ]
  • [ 104-09-6 ]
  • [ 1394846-85-5 ]
YieldReaction ConditionsOperation in experiment
73% With iron(III) chloride; In 1,2-dichloro-ethane; at 18 - 26℃; for 2h; General procedure: To a mixture of alkyne and aldehyde in 1,2-DCE was added anhydrous FeCl3. The solution was stirred at room temperature until the alkyne disappeared detected by TLC. Then the solvent was evaporated and the residue was subjected to chromatography directly eluting with petro ether to afford the corresponding product.
  • 36
  • [ 2789-88-0 ]
  • [ 4251-65-4 ]
  • [ 1394846-74-2 ]
YieldReaction ConditionsOperation in experiment
61% With iron(III) chloride; In 1,2-dichloro-ethane; at 18 - 26℃; for 2h; General procedure: To a mixture of alkyne and aldehyde in 1,2-DCE was added anhydrous FeCl3. The solution was stirred at room temperature until the alkyne disappeared detected by TLC. Then the solvent was evaporated and the residue was subjected to chromatography directly eluting with petro ether to afford the corresponding product.
  • 37
  • [ 2789-88-0 ]
  • [ 43017-75-0 ]
  • [ 1394847-06-3 ]
YieldReaction ConditionsOperation in experiment
69% With iron(III) chloride; In 1,2-dichloro-ethane; at 18 - 26℃; for 2h; General procedure: To a mixture of alkyne and aldehyde in 1,2-DCE was added anhydrous FeCl3. The solution was stirred at room temperature until the alkyne disappeared detected by TLC. Then the solvent was evaporated and the residue was subjected to chromatography directly eluting with petro ether to afford the corresponding product.
  • 38
  • [ 2789-88-0 ]
  • [ 122-78-1 ]
  • [ 1341128-23-1 ]
YieldReaction ConditionsOperation in experiment
69% With iron(III) chloride; In 1,2-dichloro-ethane; at 18 - 26℃; for 2h; General procedure: To a mixture of alkyne and aldehyde in 1,2-DCE was added anhydrous FeCl3. The solution was stirred at room temperature until the alkyne disappeared detected by TLC. Then the solvent was evaporated and the residue was subjected to chromatography directly eluting with petro ether to afford the corresponding product.
  • 39
  • [ 2789-88-0 ]
  • [ 62-53-3 ]
  • 2,3-bis(4-methylphenyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With Cp*Rh(H2O)3(OTf)2; oxygen; acetic anhydride; In pentan-1-ol; at 100℃; for 24h; The aniline to 1a (55. 0μL, 0 . 6mmol), 1, 2-diphenyl 2b (82.5 mg, 0 . 4mmol), Cp*Rh (H2O)3(OTf)2(11.8 mg, 5mol %), acetic anhydride (59. 0μL, 0 . 6mmol), adding 2.0 ml in tertiary amyl alcohol , oxygen (1atm), 100 degrees reaction 24 hours after stop the reaction, add NaOH (48 mg, 1 . 2mmol) and methanol 2 ml after stirring one hour, column chromatography get the pure product 2,3-di(4-methylphenyl)-indole 3ab. The product is white solid, yield 81%.
  • 40
  • [ 23115-42-6 ]
  • [ 2789-88-0 ]
  • [ 1431712-00-3 ]
YieldReaction ConditionsOperation in experiment
87% With potassium hexafluorophosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate; In 1,2-dimethoxyethane; at 110℃; for 10h;Inert atmosphere; General procedure: A reaction tube was charged with N-acetylenamide 1a (100 mg, 0.636 mmol), alkyne 2a (124 mg, 0.699 mmol), Cu(OAc)2.H2O (126 mg, 0.636 mmol), KPF6 (23.4 mg, 0.127 mmol) and [RuCl2(p-cymene)]2 (7.8 mg, 0.0127 mmol). To that, DME or water (3 mL) was added by syringe. The reaction mixture was stirred at 110 C under N2 as indicated time in the table 1.The reaction mixture was cooled down to rt, diluted with 10 mL of DCM. The mixture was then filtered through Celite. The combined organic portion was washed with water, then dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel with hexane/ethyl acetate as eluent to yielded the desired pyrrole 3a (202 mg, 0.605 mmol) in 95% yield. Products obtained in this work were characterized by spectral methods particularly with 1H, 13C NMR, and ESI-Mass analyses, further, the data were compared with those reported.
  • 41
  • [ 2789-88-0 ]
  • [ 4546-19-4 ]
  • [ 1443991-51-2 ]
YieldReaction ConditionsOperation in experiment
85% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; silver carbonate; In tert-butyl alcohol; at 90℃; for 16h; 3,4-Bis(4-methylphenyl)-1-ethoxybenz-[c-1,2]oxaphosphinine 1-oxide (50.0 mg, 85%) as a target compound was obtained under the condition of 90 C. for 16 hours, by the same reaction as the Example 1 above, except for using 1,2-bis(4-methylphenyl)ethyne (46.0 mg, 0.23 mmol) instead of using diphenylacetylene of the Example 1 above. (0083) 1H NMR (400 MHz, CDCl3) δ 7.96-7.90 (m, 1H), 7.46-7.37 (m, 2H), 7.25-7.07 (m, 6H), 6.97-6.94 (m, 3H), 4.30-4.16 (m, 2H), 2.38 (s, 3H), 2.26 (s, 3H), 1.30 (t, J=7.06 Hz, 3H)
  • 42
  • [ 2789-88-0 ]
  • [ 61441-33-6 ]
  • [ 1191105-49-3 ]
YieldReaction ConditionsOperation in experiment
81% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; copper(II) acetate monohydrate; In toluene; at 90℃; for 22h;Inert atmosphere; A 15-mL, oven-dried, N2-purged flask was charged with RhCp*(MeCN)3(SbF6)2 (2.5 mg, 0.009 mmol) and Cu(OAc)2·H2O (125.7 mg, 0.63 mmol) then a soln of hydrazone 1a (99.7 mg, 0.3 mmol) and PhC≡CPh (64.2 mg, 0.36 mmol) in toluene (1.5 mL) was added. The mixture was stirred at 90 C for 18 h, cooled to r.t., and diluted with EtOAc (10 mL) and H2O (30 mL). The aqueous layer was separated and extracted with EtOAc (3 × 10 mL). The organic phases were combined, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography [silica gel, PE-EtOAc (30:1)] to give a colorless solid; yield: 99.7 mg (93%); mp 195-197 C.
  • 43
  • [ 2789-88-0 ]
  • [ 100-52-7 ]
  • [ 41099-26-7 ]
YieldReaction ConditionsOperation in experiment
52% With tert.-butylhydroperoxide; ferrocene; In acetonitrile; at 80 - 140℃; 0.2 mmol of benzaldehyde, 0.3 mmol of bis-(4-methylphenyl)acetylene, 0.001 mmol of ferrocene, 0.6 mmol of t-butyl hydroperoxide, 2.0 mL of acetonitrile were added to a 10 mL reaction tube, and placed at 80-140. In an oil bath of C, the reaction is carried out for 20-30 hours. The reaction was stopped and cooled to room temperature. The reaction solution was diluted with dichloromethane and extracted three times with water. The organic phase was dried over anhydrous Na 2 SO 4 and filtered. Column chromatography gave 32.3 mg of the desired product in a yield of 52%.
51% In acetonitrile; at 140℃; for 48h;UV-irradiation; Add 2.0 mmol of the compound of formula (4), 0.5 mmol of the compound of formula (29), and 2.0 mL of acetonitrile into a 10 mL reaction tube. Under the irradiation of a 250W ultraviolet lamp with a maximum wavelength of 365nm, place it in an oil bath at 140C and react for 48h .Stop the reaction, cool to room temperature, add dichloromethane for dilution, extract three times with water, dry the organic phase with anhydrous sodium sulfate, filter, and separate the filtrate by column chromatography to obtain 79 mg of the compound of formula (30) with a yield of 51%.
  • 44
  • [ 1271-86-9 ]
  • [ 2789-88-0 ]
  • (Sp)-1-[(N,N-dimethylamino)methyl]-2-(6-methyl-2,3,4-tri(p-tolyl)naphthalen-1-yl)ferrocene [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With t-Boc-L-valine; tetrabutylammomium bromide; oxygen; palladium diacetate; potassium carbonate; In N,N-dimethyl acetamide; at 80℃; for 48h; General procedure: To a solution of alkyne 2 (0.46 mmol) in DMA (1.5 mL) wasadded Boc-L-Val-OH (8.7 mg, 0.04 mmol), Pd(OAc)2 (4.5 mg,0.02 mmol), K2CO3 (27.6 mg, 0.2 mmol), TBAB (tetrabutylammonium bromide) (16.1 mg, 0.05 mmol) and ferrocene 1(0.02 mmol) successively. The mixture was stirred at 80 C under air (open flask) for 48 h. After the reaction was complete,it was quenched with saturated aqueous NaHCO3 solution and extracted with EtOAc for three times. The combined organic layers were washed with H2O and brine successively, then driedover anhydrous Na2SO4 and filtrated. After the solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether 1:10, v/v, 3% Et3N) to afford the desired product 3.
  • 45
  • [ 2789-88-0 ]
  • [ 1707-03-5 ]
  • 3,4-bis(4-methylphenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; silver carbonate; In tert-butyl alcohol; at 90℃; for 16h; 3,4-Bis(4-methylphenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide (54.5 mg, 86%) as a target product was obtained under the condition of 90 C. for 16 hours, by the same reaction as the Example 1 above, except for using diphenylphosphinic acid (32.7 mg, 0.15 mmol) instead of using phenylphosphonic monoethyl ester of the Example 1 above, and using 1,2-di-p-tolylethyne (46.4 mg, 0.23 mmol) instead of using diphenylacetylene of the Example 1 above. (0194) 1H NMR (400 MHz, CDCl3) δ 7.95-7.90 (m, 2H), 7.62-7.48 (m, 4H), 7.43 (t, J=7.7 Hz, 1H), 7.33-7.29 (m, 1H), 7.21-7.13 (m, 6H), 7.05 (dd, J=8.4, 4.8 Hz, 1H), 6.92 (d, J=8.1, 2H), 2.40 (s, 3H), 2.24 (s, 3H)
82% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; silver carbonate; In 1,2-dichloro-ethane; at 110℃; for 0.5h;Microwave irradiation; In a 10mL microwave reaction tube, add compound I-1 (0.3mmol), compound II-2 (0.36mmol), Ag2CO3 (0.6mmol), NaHCO3 (0.30mmol), [RhCp*Cl2]2 (0.012mmol) ), 1,2-dichloroethane (1.5 mL), the mixture was placed in a microwave reactor at 110 C. for 30 min at a microwave power of 100 w; TLC (thin layer chromatography) detected until the reaction was complete. Purification by post-treatment: cooling to room temperature, pressure concentration. The crude product was separated and purified by silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 15:1 to 2:1, and then the pure product was obtained as a brown solid, and the yield: 82%.
  • 46
  • [ 2789-88-0 ]
  • [ 3376-24-7 ]
  • [ 41099-26-7 ]
  • 47
  • [ 5849-47-8 ]
  • [ 2789-88-0 ]
  • [ 1636893-32-7 ]
YieldReaction ConditionsOperation in experiment
74% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; silver carbonate In <i>tert</i>-butyl alcohol at 90℃; for 16h;
  • 48
  • [ 2789-88-0 ]
  • [ 7606-13-5 ]
  • [ 1609562-72-2 ]
YieldReaction ConditionsOperation in experiment
88% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In 1,2-dichloro-ethane; at 120℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: N,N-Diethylpicolinamide (1; 0.2 mmol, 1.0 equiv), [Cp*RhCl2]2 (0.005 mmol, 2.5 mol%), AgSbF6 (0.02 mmol, 10 mol%), Cu(OAc)2 (0.4 mmol, 2.0 equiv), alkyne 2 (0.44 mmol, 2.2 equiv) and DCE (2 mL) were added to a 20-mL Schlenk tube. After being purged with nitrogen, the mixture was stirred at 120 C for 24 h. Then concd aq NH3 (2 mL) was added and stirred for 5 min. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on silica gel to afford isoquinoline 3.
  • 49
  • [ 2789-88-0 ]
  • [ 5311-82-0 ]
  • [ 130162-56-0 ]
YieldReaction ConditionsOperation in experiment
92% With 1,2,3,4-tetraphenylcyclopentadiene; tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate; copper diacetate; In N,N-dimethyl-formamide; at 120℃;Schlenk technique; Inert atmosphere; General procedure: A Schlenk tube was charged with alkyne 2 (0.30 mmol), [Cp*Rh(MeCN)3](SbF6)2(0.010 mmol), C5H2Ph4 (0.020 mmol), and Cu(OAc)2 (0.40 mmol), and the tube was evacuated and back filled with nitrogen. Alkylidenehydrazine 1 (0.20 mmol) and DMF (1.0 mL) were added via a syringe through the septum, and the mixture was heated at 120C for 3-9 h. After cooling to room temperature, the reaction mixture was filtered through a plugof silica gel washing with hexane-AcOEt (10:1), and the filtrate was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane:AcOEt = 30:1) to afford indole 3.
  • 50
  • [ 2789-88-0 ]
  • [ 673485-54-6 ]
  • [ 1610537-55-7 ]
YieldReaction ConditionsOperation in experiment
94% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; acetic acid at 120℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;
  • 51
  • [ 2789-88-0 ]
  • [ 6954-68-3 ]
  • [ 1629249-03-1 ]
YieldReaction ConditionsOperation in experiment
68% With palladium diacetate; copper(II) bis(trifluoromethanesulfonate); silver(l) oxide; In N,N-dimethyl acetamide; at 120℃; for 12h;Inert atmosphere; Schlenk technique; General procedure: To a Schlenk tube, a 3-(acetylamino)carbazole 1 (0.4 mmol), a diarylacetylene 2 (0.6 mmol), Pd(OAc)2 (10 mol%), Ag2O (1.0equiv), Cu(OTf)2 (1.0 equiv) and DMA (3.0 mL) were added successivelyunder N2. The mixture was stirred at r.t. for a few min. Then, the tube was placed in a preheated (120 C) oil bath, and stirred. After completion of the reaction (TLC monitoring), the solution was cooled to r.t., diluted with EtOAc (30 mL), washed with H2O (10 mL), dried over anhydrous Na2SO4, filtered and concentratedunder reduced pressure. The residue was purified by columnchromatography (hexanes-EtOAc, 8.5:1.5) to afford the product 3.
  • 52
  • [ 2789-88-0 ]
  • [ 88-61-9 ]
  • 6,8-dimethyl-3,4-di-p-tolylbenzo[c][1,2]oxathiine 1,1-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In 1,4-dioxane at 100℃; for 16h; Sealed tube; Inert atmosphere; Schlenk technique;
  • 53
  • [ 36122-35-7 ]
  • [ 2789-88-0 ]
  • C25H20O2 [ No CAS ]
  • 54
  • [ 5378-52-9 ]
  • [ 2789-88-0 ]
  • 3,4-bis(4-methylphenyl)-2-aminoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate; copper(II) acetate monohydrate; In N,N-dimethyl-formamide; at 120℃; for 6.0h;Sealed tube; Inert atmosphere; Green chemistry; 1032 g were weighed in this order1,2-bis (4-methylphenyl) acetylene (0.5 mmol),0.2191 g of <strong>[5378-52-9]phenyl-1H-tetrazole</strong> (1.5 mmol),0 ? 0031 g [Cp * RhCl2] 2 (0. 005 mmol),0 ? 1997g Cu (OAc) 2 .H20 (1.0mmol) and0,0984 g of potassium acetate (1.O mmol) was addedIn a 25 mL sealed tube containing a magnetic stir bar,2. OmL N, N-diethylformamide was added.The cannula was sealed under nitrogen,The mixture was stirred in an oil bath at 120 C for 6 hours.After the end of the reaction, the column was separated with petroleum ether-ethyl acetate as the eluent,Obtained as a white solid, 0.1054 g,Target productThe isolated yield of 3,4-bis (4-methylphenyl) -2-aminoisoquinoline was 65%.
  • 55
  • [ 5378-52-9 ]
  • [ 2789-88-0 ]
  • 2-phenyl-4,5-di-p-tolylimidazo[1,2-a]quinoline [ No CAS ]
  • 56
  • [ 2789-88-0 ]
  • [ 114-83-0 ]
  • N-(2,3-di-p-tolyl-1H-indol-1-yl)acetamide [ No CAS ]
  • 57
  • [ 2789-88-0 ]
  • [ 131222-99-6 ]
  • 4,5-di(4-tolyl)cyclopenta[hi]chrysene [ No CAS ]
  • 4,5,10,11-tetra(4-tolyl)dicyclopenta[hi,qr]chrysene [ No CAS ]
  • 58
  • [ 2789-88-0 ]
  • [ 4105-21-9 ]
  • 5,6-di-p-tolylnaphtho[1′,2′:4,5]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; caesium carbonate; In toluene; at 125℃; for 7h;Inert atmosphere; General procedure: In a oven-dried RBF, a solution of Imidazo[1,2,-a]pyridines derivatives 1 (0.5 mmol) and alkyne2 in toluene (2 mL) [Cp*RhCl2]2 (5 mol%), Cu(OAc)2·H2O (2 equiv), Cs2CO3 (30 mol%) wereadded under inert atmosphere. The resulting reaction mixture was heated at 125 C for 7 h.Progression of the reaction was monitored by TLC, while noticing complete consumption ofImidazo[1,2,-a]pyridines derivatives, reaction was brought to room temperature. The additionalamount of acrylate also added if required for complete conversion. The reaction mixture wasdiluted with ethyl acetate (10 mL) and water (15 mL) and then filtered through a plug of celite.The layers were separated, and the organic layer was washed with aqueous saturated brinesolution, dried over Na2SO4. Organic layer was concentrated under reduced pressure.The crudematerial so obtained was purified by column chromatography on silica gel (hexane: ethylacetate :: 70:30). The structure and purity of known starting materials were confirmed by comparison oftheir physical and spectral data (1H NMR, 13C NMR and HRMS ).
80% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cobalt(II) diacetate tetrahydrate; In N,N-dimethyl-formamide; at 110℃; for 2h;Sealed tube; General procedure: A 10 mL vial was charged the requisite 2-arylimidazo[1,2-a]pyridine derivatives (1.0 equiv), internal alkynes (2.0 equiv), Co(OAc)2·4H2O (1.2 equiv) and [RhCp*Cl2]2 (5 mol%) in DMF (1 mL). The vial was sealed, heated to 110 C and stirred for 2 h. The resulting mixture was analyzed by TLC. After cooling to room temperature, the mixture was concentrated in vacuo. The products were isolated by silica gel with ethyl acetate and petroleum ether as the eluent to afford the desired products.
  • 59
  • [ 2789-88-0 ]
  • [ 201024-81-9 ]
  • C29H25NO [ No CAS ]
  • C29H25NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid; In ethyl acetate; at 80℃; for 15h;Sealed tube; Inert atmosphere; General procedure: Nitrones (0.2 mmol), diarylacetylenes (0.3 mmol), [Cp*RhCl2]2 (4 mol%), AgSbF6 (16 mol%), PivOH (2.0 equiv)and ethyl acetate (2 mL) were charged into the sealed tube. The reaction mixture was stirred at 80 C for 15 h. After cooled to room temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using triethylamine/PE or PE/EA to afford compounds 3.
  • 60
  • [ 92961-15-4 ]
  • [ 2789-88-0 ]
  • 2-phenyl-3,4-di-p-tolylimidazo[5,1,2-cd]indolizine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With palladium diacetate; copper(II) acetate monohydrate; In dimethyl sulfoxide; at 110℃; for 12h;Sealed tube; General procedure: A mixture of 2-phenylimidazo[1,2-a]pyridine(1) (0.25 mmol, 48.5 mg) and diphenylacetylene(2) (0.25 mmol, 44.5 mg) was takenin a sealed tube followed by addition of Pd(OAc)2 (5 mol %, 3 mg), (1equiv, 50 mg Cu(OAc)2.H2O) and DMSO (1 mL) under air. Theresulting mixture was stirred at 110 C for 12 h. Upon cooling to roomtemperature, the reaction mixture was extracted with ethyl acetate. The organicphase was dried over anhydrous Na2SO4 and concentratedunder reduced pressure to get the crude residue which was purified by columnchromatography on silica gel (60-120 mesh) using petroleum ether:ethyl acetate= 9:1 as an eluent to afford the pure olefinated product (3aa) (72 mg, 78%) as a yellow oil.
  • 61
  • [ 2789-88-0 ]
  • [ 882187-78-2 ]
  • C30H24N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With palladium diacetate; copper(II) acetate monohydrate; In dimethyl sulfoxide; at 110℃; for 12h;Sealed tube; General procedure: A mixture of 2-phenylimidazo[1,2-a]pyridine(1) (0.25 mmol, 48.5 mg) and diphenylacetylene(2) (0.25 mmol, 44.5 mg) was takenin a sealed tube followed by addition of Pd(OAc)2 (5 mol %, 3 mg), (1equiv, 50 mg Cu(OAc)2.H2O) and DMSO (1 mL) under air. Theresulting mixture was stirred at 110 C for 12 h. Upon cooling to roomtemperature, the reaction mixture was extracted with ethyl acetate. The organicphase was dried over anhydrous Na2SO4 and concentratedunder reduced pressure to get the crude residue which was purified by columnchromatography on silica gel (60-120 mesh) using petroleum ether:ethyl acetate= 9:1 as an eluent to afford the pure olefinated product (3aa) (72 mg, 78%) as a yellow oil.
  • 62
  • [ 3112-85-4 ]
  • [ 2789-88-0 ]
  • (E)-1-(2-(methylsulfonyl)phenyl)-1,2-bis(4-methylphenyl)ethene [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; 1-Adamantanecarboxylic acid In chlorobenzene at 140℃; for 24h; Inert atmosphere; regioselective reaction; 4.6. Reaction of methyl phenyl sulfones 1 with alkynes 2 General procedure: To a 20 mL two-necked flask with a reflux condenser, a balloon,and a rubber cup were added methyl phenyl sulfone 1 (0.75 mmol),alkyne 2 (0.25 mmol), [Cp*Rh(MeCN)3](SbF6)2 (0.01 mmol, 8.3 mg),1-AdCOOH (0.1 mmol, 18 mg), 1-methylnaphlene (ca. 30 mg) as internal standard, and PhCl (1 mL). Then, the resulting mixture was stirred under nitrogen at 140 C for 24 h. After cooling, the reaction mixture was extracted with ethyl acetate (100 mL). The organic layer was washed by aqueous NaHCO3 (100 mL, three times) and dried over Na2SO4. After evaporation of the solvents under vacuum,product 3 was isolated by column chromatography on silica gel using hexane/ethyl acetate as eluent. Further purification by gel permeation chromatography (GPC) was performed, if needed.
  • 63
  • [ 2789-88-0 ]
  • [ 15563-32-3 ]
  • [ 41099-26-7 ]
YieldReaction ConditionsOperation in experiment
79% With silver hexafluoroantimonate; [RhCp*(CH3CN)3] (SbF6)2; copper(II) acetate monohydrate; In diethylene glycol dimethyl ether; at 140℃; for 4h;Inert atmosphere; General procedure: To a 20 mL two-necked flask with a reflux condenser, a balloon, and a rubber cup were added thioamide 1 (0.25 mmol), alkyne 4 (0.25 mmol), [Cp*Rh(MeCN)3][SbF6]2 (0.01 mmol, 8.3 mg), AgSbF6 (0.04 mmol, 14 mg), Cu(OAc)2•H2O (0.5 mmol, 100 mg), dibenzyl (ca. 30 mg) as internal standard, and diglyme (3 mL). Then, the resulting mixture was stirred under nitrogen at 140 C (bath temperature) for 4 h. After cooling, to the reaction mixture were added water (30 mL) and ethylenediamine (2 mL). The mixture was extracted with ethyl acetate (3x30 mL) and dried over Na2SO4. After evaporation of the solvents under vacuum, product 5 was isolated by column chromatography using eluent shown below. Further purification by gel permeation chromatography (GPC) was performed, if needed.
  • 64
  • [ 31562-99-9 ]
  • [ 2789-88-0 ]
  • 3-methoxy-5,6-di-p-tolylnaphtho[1',2':4,5]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; caesium carbonate; In toluene; at 125℃; for 7h;Inert atmosphere; General procedure: In a oven-dried RBF, a solution of Imidazo[1,2,-a]pyridines derivatives 1 (0.5 mmol) and alkyne2 in toluene (2 mL) [Cp*RhCl2]2 (5 mol%), Cu(OAc)2·H2O (2 equiv), Cs2CO3 (30 mol%) wereadded under inert atmosphere. The resulting reaction mixture was heated at 125 C for 7 h.Progression of the reaction was monitored by TLC, while noticing complete consumption ofImidazo[1,2,-a]pyridines derivatives, reaction was brought to room temperature. The additionalamount of acrylate also added if required for complete conversion. The reaction mixture wasdiluted with ethyl acetate (10 mL) and water (15 mL) and then filtered through a plug of celite.The layers were separated, and the organic layer was washed with aqueous saturated brinesolution, dried over Na2SO4. Organic layer was concentrated under reduced pressure.The crudematerial so obtained was purified by column chromatography on silica gel (hexane: ethylacetate :: 70:30). The structure and purity of known starting materials were confirmed by comparison oftheir physical and spectral data (1H NMR, 13C NMR and HRMS ).
  • 65
  • [ 2789-88-0 ]
  • [ 885-91-6 ]
  • 10-methyl-5,6-di-p-tolylnaphtho[1',2':4,5]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; caesium carbonate; In toluene; at 125℃; for 7h;Inert atmosphere; General procedure: In a oven-dried RBF, a solution of Imidazo[1,2,-a]pyridines derivatives 1 (0.5 mmol) and alkyne2 in toluene (2 mL) [Cp*RhCl2]2 (5 mol%), Cu(OAc)2·H2O (2 equiv), Cs2CO3 (30 mol%) wereadded under inert atmosphere. The resulting reaction mixture was heated at 125 C for 7 h.Progression of the reaction was monitored by TLC, while noticing complete consumption ofImidazo[1,2,-a]pyridines derivatives, reaction was brought to room temperature. The additionalamount of acrylate also added if required for complete conversion. The reaction mixture wasdiluted with ethyl acetate (10 mL) and water (15 mL) and then filtered through a plug of celite.The layers were separated, and the organic layer was washed with aqueous saturated brinesolution, dried over Na2SO4. Organic layer was concentrated under reduced pressure.The crudematerial so obtained was purified by column chromatography on silica gel (hexane: ethylacetate :: 70:30). The structure and purity of known starting materials were confirmed by comparison oftheir physical and spectral data (1H NMR, 13C NMR and HRMS ).
83% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cobalt(II) diacetate tetrahydrate; In N,N-dimethyl-formamide; at 110℃; for 2h;Sealed tube; General procedure: A 10 mL vial was charged the requisite 2-arylimidazo[1,2-a]pyridine derivatives (1.0 equiv), internal alkynes (2.0 equiv), Co(OAc)2·4H2O (1.2 equiv) and [RhCp*Cl2]2 (5 mol%) in DMF (1 mL). The vial was sealed, heated to 110 C and stirred for 2 h. The resulting mixture was analyzed by TLC. After cooling to room temperature, the mixture was concentrated in vacuo. The products were isolated by silica gel with ethyl acetate and petroleum ether as the eluent to afford the desired products.
  • 66
  • [ 65964-63-8 ]
  • [ 2789-88-0 ]
  • 3-methoxy-10-methyl-5,6-di-p-tolylnaphtho[1',2':4,5]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; caesium carbonate; In toluene; at 125℃; for 7h;Inert atmosphere; General procedure: In a oven-dried RBF, a solution of Imidazo[1,2,-a]pyridines derivatives 1 (0.5 mmol) and alkyne2 in toluene (2 mL) [Cp*RhCl2]2 (5 mol%), Cu(OAc)2·H2O (2 equiv), Cs2CO3 (30 mol%) wereadded under inert atmosphere. The resulting reaction mixture was heated at 125 C for 7 h.Progression of the reaction was monitored by TLC, while noticing complete consumption ofImidazo[1,2,-a]pyridines derivatives, reaction was brought to room temperature. The additionalamount of acrylate also added if required for complete conversion. The reaction mixture wasdiluted with ethyl acetate (10 mL) and water (15 mL) and then filtered through a plug of celite.The layers were separated, and the organic layer was washed with aqueous saturated brinesolution, dried over Na2SO4. Organic layer was concentrated under reduced pressure.The crudematerial so obtained was purified by column chromatography on silica gel (hexane: ethylacetate :: 70:30). The structure and purity of known starting materials were confirmed by comparison oftheir physical and spectral data (1H NMR, 13C NMR and HRMS ).
61% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cobalt(II) diacetate tetrahydrate; In N,N-dimethyl-formamide; at 110℃; for 2h;Sealed tube; General procedure: A 10 mL vial was charged the requisite 2-arylimidazo[1,2-a]pyridine derivatives (1.0 equiv), internal alkynes (2.0 equiv), Co(OAc)2·4H2O (1.2 equiv) and [RhCp*Cl2]2 (5 mol%) in DMF (1 mL). The vial was sealed, heated to 110 C and stirred for 2 h. The resulting mixture was analyzed by TLC. After cooling to room temperature, the mixture was concentrated in vacuo. The products were isolated by silica gel with ethyl acetate and petroleum ether as the eluent to afford the desired products.
  • 67
  • [ 2789-88-0 ]
  • [ 1019-89-2 ]
  • 9-methyl-5,6-di-p-tolylnaphtho[1',2':,5]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; caesium carbonate; In toluene; at 125℃; for 7h;Inert atmosphere; General procedure: In a oven-dried RBF, a solution of Imidazo[1,2,-a]pyridines derivatives 1 (0.5 mmol) and alkyne2 in toluene (2 mL) [Cp*RhCl2]2 (5 mol%), Cu(OAc)2·H2O (2 equiv), Cs2CO3 (30 mol%) wereadded under inert atmosphere. The resulting reaction mixture was heated at 125 C for 7 h.Progression of the reaction was monitored by TLC, while noticing complete consumption ofImidazo[1,2,-a]pyridines derivatives, reaction was brought to room temperature. The additionalamount of acrylate also added if required for complete conversion. The reaction mixture wasdiluted with ethyl acetate (10 mL) and water (15 mL) and then filtered through a plug of celite.The layers were separated, and the organic layer was washed with aqueous saturated brinesolution, dried over Na2SO4. Organic layer was concentrated under reduced pressure.The crudematerial so obtained was purified by column chromatography on silica gel (hexane: ethylacetate :: 70:30). The structure and purity of known starting materials were confirmed by comparison oftheir physical and spectral data (1H NMR, 13C NMR and HRMS ).
  • 68
  • [ 2789-88-0 ]
  • [ 365213-32-7 ]
  • 3-methoxy-9-methyl-5,6-di-p-tolylnaphtho[1',2':4,5]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; caesium carbonate; In toluene; at 125℃; for 7h;Inert atmosphere; General procedure: In a oven-dried RBF, a solution of Imidazo[1,2,-a]pyridines derivatives 1 (0.5 mmol) and alkyne2 in toluene (2 mL) [Cp*RhCl2]2 (5 mol%), Cu(OAc)2·H2O (2 equiv), Cs2CO3 (30 mol%) wereadded under inert atmosphere. The resulting reaction mixture was heated at 125 C for 7 h.Progression of the reaction was monitored by TLC, while noticing complete consumption ofImidazo[1,2,-a]pyridines derivatives, reaction was brought to room temperature. The additionalamount of acrylate also added if required for complete conversion. The reaction mixture wasdiluted with ethyl acetate (10 mL) and water (15 mL) and then filtered through a plug of celite.The layers were separated, and the organic layer was washed with aqueous saturated brinesolution, dried over Na2SO4. Organic layer was concentrated under reduced pressure.The crudematerial so obtained was purified by column chromatography on silica gel (hexane: ethylacetate :: 70:30). The structure and purity of known starting materials were confirmed by comparison oftheir physical and spectral data (1H NMR, 13C NMR and HRMS ).
  • 69
  • [ 2789-88-0 ]
  • C18H16N2O2 [ No CAS ]
  • (E)-ethyl 3-(5,6-di-p-tolylnaphtho[1',2':4,5]imidazo[1,2-a]pyridin-3-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; caesium carbonate; In toluene; at 120℃; for 7h; In a oven-dried RBF, a solution of Imidazo[1,2,-a]pyridines derivatives 1 (0.5 mmol) and alkyne2 in toluene (2 mL) [Cp*RhCl2]2 (5 mol%), Cu(OAc)2·H2O (2 equiv), Cs2CO3 (30 mol%) wereadded under inert atmosphere. The resulting reaction mixture was heated at 125 C for 7 h.Progression of the reaction was monitored by TLC, while noticing complete consumption ofImidazo[1,2,-a]pyridines derivatives, reaction was brought to room temperature. The additionalamount of acrylate also added if required for complete conversion. The reaction mixture wasdiluted with ethyl acetate (10 mL) and water (15 mL) and then filtered through a plug of celite.The layers were separated, and the organic layer was washed with aqueous saturated brinesolution, dried over Na2SO4. Organic layer was concentrated under reduced pressure.The crudematerial so obtained was purified by column chromatography on silica gel (hexane: ethylacetate :: 70:30). The structure and purity of known starting materials were confirmed by comparison oftheir physical and spectral data (1H NMR, 13C NMR and HRMS ).
  • 70
  • [ 613-91-2 ]
  • [ 2789-88-0 ]
  • 1-methyl-3,4-di(p-tolyl)isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper(II) acetate monohydrate; Trimethylacetic acid; In methanol; at 120℃; for 24h;Sealed tube; General procedure: A mixture of acetophenone oxime 1a (0.2 mmol), diphenylacetylene 2 (0.24 mmol, 1.2 equiv), [Cp*IrCl2]2 (3 mol%), PivOH (0.06 mmol, 0.3 equiv), Cu(OAc)2. H2O (0.4 mmol, 2 equiv) and MeOH (2 mL) in a 15mL glass vial [sealed with poly(tetrafluoroethylene)(PTFE) cap] was heated at 120 C with vigorous stirring for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through Celite. The filtrate was concentrated in vacuo and purified by column chromatography on silica gel to give the corresponding product 4. 1-Methyl-3,4-di-p-tolylisoquinoline (4a) White solid; 1H NMR (400 MHz, CDCl3) d 8.21e8.19 (m, 1H), 7.69-7.67 (m, 1H), 7.60-7.58 (m, 2H), 7.32-7.28 (m, 2H), 7.20-7.13(m, 4H), 7.04 (d, J 8.0 Hz, 2H), 3.09 (s, 3H), 2.42 (s, 3H), 2.31 (s,3H); 13C NMR (100 MHz, CDCl3) d 157.4, 149.4, 138.3, 136.6, 136.5, 136.3, 134.7, 131.2, 130.2, 129.7, 129.0, 128.9, 128.4, 126.3, 126.1, 125.5, 22.7, 21.3, 21.2; HRMS: m/z calcd for C24H22N [MH]: 324.1752; Found: 324.1762.
  • 71
  • [ 42918-20-7 ]
  • [ 2789-88-0 ]
  • 3-methyl-1,2-di-p-tolylnaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With palladium(II) trifluoroacetate; caesium carbonate; glyoxal bis(N-methyl-N-phenylhydrazone) In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;
  • 72
  • [ 65964-61-6 ]
  • [ 2789-88-0 ]
  • 3,10-dimethyl-5,6-di-p-tolylnaphtho[1',2':4,5]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cobalt(II) diacetate tetrahydrate; In N,N-dimethyl-formamide; at 110℃; for 2h;Sealed tube; General procedure: A 10 mL vial was charged the requisite 2-arylimidazo[1,2-a]pyridine derivatives (1.0 equiv), internal alkynes (2.0 equiv), Co(OAc)2·4H2O (1.2 equiv) and [RhCp*Cl2]2 (5 mol%) in DMF (1 mL). The vial was sealed, heated to 110 C and stirred for 2 h. The resulting mixture was analyzed by TLC. After cooling to room temperature, the mixture was concentrated in vacuo. The products were isolated by silica gel with ethyl acetate and petroleum ether as the eluent to afford the desired products.
  • 73
  • [ 2789-88-0 ]
  • [ 65964-60-5 ]
  • 3-methyl-5,6-di-p-tolylnaphtho[1',2':4,5]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cobalt(II) diacetate tetrahydrate; In N,N-dimethyl-formamide; at 110℃; for 2h;Sealed tube; General procedure: A 10 mL vial was charged the requisite 2-arylimidazo[1,2-a]pyridine derivatives (1.0 equiv), internal alkynes (2.0 equiv), Co(OAc)2·4H2O (1.2 equiv) and [RhCp*Cl2]2 (5 mol%) in DMF (1 mL). The vial was sealed, heated to 110 C and stirred for 2 h. The resulting mixture was analyzed by TLC. After cooling to room temperature, the mixture was concentrated in vacuo. The products were isolated by silica gel with ethyl acetate and petroleum ether as the eluent to afford the desired products.
  • 74
  • [ 2789-88-0 ]
  • 4,5-bis(4-methylphenyl)-2H-1,2,3-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With sodium azide; [bis(acetoxy)iodo]benzene; In acetonitrile; at 20℃; for 8h;Schlenk technique; Add 1,2-<strong>[2789-88-0]di-p-tolylacetylene</strong> (0.20 mmol), NaN3 (0.3 mmol), PhI(OAc)2 (0.2 mmol) to a clean 25 mL Schlenk tube, and add 3 mL of CH3CN as solvent.After reacting for 8 hours at room temperature, the TLC plate was tested. After the reaction was completed, the reaction solution was added with an appropriate amount of water and extracted with ethyl acetate (3×10 mL).The organic phases were combined and dried over anhydrous Na 2 SO 4 .The organic layer was concentrated and subjected to column chromatography to yield purified 4,5-di-p-tolyl-2H-1,2,3-triazole as a pale yellow solid, yield 93%.
  • 75
  • [ 2789-88-0 ]
  • [ 18869-29-9 ]
  • [ 2510-76-1 ]
YieldReaction ConditionsOperation in experiment
With [{CyPN(H)P}Co(CH2SiMe3)]-BArF4; hydrogen In tetrahydrofuran at 25℃;
84 % de With formic acid; potassium carbonate In acetonitrile at 80℃; for 2.5h; Overall yield = 86 percentSpectr.;
  • 76
  • [ 2789-88-0 ]
  • [ 611-73-4 ]
  • C24H20O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With boron trifluoride diethyl etherate; In fluorobenzene; at 70℃; for 2h; In a reaction tube0. 3 mmol of benzoylformic acid,0. 6 mmol of bis (4-methylphenyl) acetylene,0. 09 mmol of boron trifluoride etherate and 2 mL of fluorobenzene at 70 C for 2 h. After completion of the reaction, the solvent was distilled off under reduced pressure, and the mixture was further subjected to column chromatography using a mixture of petroleum ether and ethyl acetate. The volume ratio of ethyl acetate was 5: 1, then the pure product was obtained in 85% yield with a purity of 98%.
  • 77
  • [ 2789-88-0 ]
  • [ 101-42-8 ]
  • N,N-dimethyl-2,3-di-p-tolyl-1H-indole-1-carboxamide [ No CAS ]
  • 78
  • [ 2789-88-0 ]
  • [ 134-11-2 ]
  • (E)-{1-(3-ethoxyphenyl)-1,2-bis-[p-tolyl]ethene [ No CAS ]
  • 79
  • [ 1493-13-6 ]
  • [ 2789-88-0 ]
  • (E)-N-benzylidenebenzenamine [ No CAS ]
  • 2-phenyl-3,4-di-p-tolylisoquinolinium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; In methanol; at 90℃; for 1h;Inert atmosphere; General procedure: (E)-N-Benzylideneaniline 1a (19.7 mg, 0.10 mmol), diphenylacetylene 2a (26.7 mg, 0.15 mmol), [Cp*RhCl2]2 (3.1 mg, 5 mol%), Cu(OAc)2.H2O (20 mg, 1 equiv) and trifluoromethanesulfonic acid (15mg, 1 equiv) were stirred in MeOH (1 mL) at 90 C for 1 h. After completion, the reaction mixture was purified by flash chromatography eluting with CH2Cl2 and MeOH (10:1) to give the desired product 3aa as a grey solid (42.6 mg, 82%).
72% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; In methanol; at 90℃; for 1h;Inert atmosphere; General procedure: (E)-N-Benzylideneaniline 1a (19.7 mg, 0.10 mmol), diphenylacetylene 2a (26.7 mg, 0.15 mmol),[Cp*RhCl2]2 (3.1 mg, 5 mol%), Cu(OAc)2H2O (20 mg, 1 equiv) and trifluoromethanesulfonic acid (15mg, 1 equiv) were stirred in MeOH (1 mL) at 90 C for 1 h. After completion, the reaction mixture waspurified by flash chromatography eluting with CH2Cl2 and MeOH (10:1) to give the desired product 3aaas a grey solid (42.6 mg, 82%).
  • 80
  • [ 2789-88-0 ]
  • [ 21399-33-7 ]
  • [ 1613470-76-0 ]
YieldReaction ConditionsOperation in experiment
75% With Cp*Rh(H2O)3(OTf)2; benzoic acid; In methanol; at 25℃; for 24h; The phenylhydrazone 4b (0.3mmol), 1,2-bis(4-methylphenyl) acetylene 2b (0.5mmol), Cp*Rh (H2O)3(OTf)2(0.01mmol), benzoic acid (0.125mmol), by adding 4.0 ml methanol, the air lower, 25oC reaction 24 hours after cessation of the reaction, pure product of column chromatography to obtain isoquinoline 4bb. The product is white solid, yield 75%.
  • 81
  • [ 64-18-6 ]
  • [ 2789-88-0 ]
  • [ 32383-64-5 ]
YieldReaction ConditionsOperation in experiment
86% With 1,3-bis-(diphenylphosphino)propane; bis(acetylacetonate)nickel; 2,2-dimethylpropanoic anhydride; In toluene; at 100℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: The method as in Example 1, yield 86%, purity> 99%.In a 10mL Schlenk reaction tube (Hinwil Beijing GlassInstrument Co., F891410 reaction tube, the capacity of 10mL, 14/20 groundjoint) was added bis (acetylacetonate) Ni (5mol%, 6.5mg) and 1,2-bis (diphenylphosphino) benzene (7mol%, 15.6mg), was fully replaced with argon threetimes the air tube, under an argon atmosphere and then add 1ml of toluene,diphenyl acetylene (0.50mmol, 89.2mg), formic acid (1.1mmol, 50.6 mg) andpivalic anhydride (20mol%, 0.1mmol, 18.4mg); the reaction system was heated inan oil bath to 100 deg.] C and stirring was continued for 24 hours (using anIKA magnetic stirrer, the RCT basic, stirring speed of 500 rpm /minute). Aftercompletion of the reaction, the system was cooled to room temperature. Thereaction solution was diluted with ethyl acetate, and then the reactionsolution was diluted with a rotary evaporator and concentrated way (Buchi,Switzerland Ltd., by BUCHI Rotavapor R-3). Concentrated residue was purified bycolumn (Hinwil Beijing Glass Instrument Co., C383040C ball with sand boardstorage column, 5/20, φ30mm, effective length: 500ml) chromatography to givethe product.The product as a white solid, 109 mg, 98% yield,, purity>99%, eluent ethyl acetate: petroleum ether = 1: 50 to 1:10.Means of NMR obtained in Example 1 (E) -2,3- diphenyl-α, β-unsaturated carboxylic acid analysis, proton nuclear magnetic resonancespectrum thereof obtained as shown in FIG. 1; its 13C to give shown in FIGURE2.
  • 82
  • [ 891782-22-2 ]
  • [ 2789-88-0 ]
  • [ 1191105-49-3 ]
YieldReaction ConditionsOperation in experiment
75% General procedure: N-Sulfinyl imine (1a, 57.1 mg, 0.2 mmol), CoCp*(CO)I2 (9.5 mg, 10 mol%), AgNTf2 (15.5 mg, 20 mol%), HOAc (12 mg, 1.0 equiv.), and diphenylacetylene (2a, 42.8 mg, 1.2 equiv.) were weighed into a pressure tube, to which was added 1,2-dichloroethane (3 mL) under N2. The reaction mixture was stirred for 18 h at 120 C. After removal of 1,2-dichloroethane under reduced pressure, methanol (3 mL) was added, followed by addition of sodium borohydride (22.8 mg, 3 equiv.). The hydrolyzed benzophenone by-product and the isoquinolines product accidentally have the same Rf in chromatography, so NaBH4 was added to convert benzophenone to the corresponding alcohol. The mixture was stirred at room temperature for 30 min. Purification was performed by flash column chromatography on silica gel using EtOAc and petroleum ether to afford the desired product.
  • 83
  • [ 2789-88-0 ]
  • [ 1122-91-4 ]
  • 5-methyl-2-(p-methylphenyl)-3-(p-bromophenyl)-1-indanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With methyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 50℃; for 24h;Sealed tube; To a 25mL reactor, were added <strong>[2789-88-0]1,2-bis(4-methylphenyl)acetylene</strong> (0.22mmol, 46mg),4-bromobenzaldehyde (0.2mmol, 37mg), methyl trifluoromethanesulfonate (0.04mmol, 4.6μL), finally adding 0.5mL 1,2-dichloroethane as solvent, sealed reactor, 50 deg. C for 24 hours. After the reaction system was cooled, 15mL water and 15mL of dichloromethane was added and stirred for 30min, and then extracted with 15mL of dichloromethane three times, the organic phases combined.The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate for 0.5h and finally , the organic phase was filtered and rotary evaporated to give the crude product. The crude product with petroleum ether: ethyl acetate = 25: 1 (volume ratio) as eluent, silica gel 200 to 300 mesh phase adsorption column chromatography, to obtain a purity greater than 99% of a pale yellow solid product 55-methyl-2-(p-methylphenyl)-3-(p-bromophenyl)-1-indanone 74mg, 94% yield.
  • 84
  • [ 2789-88-0 ]
  • [ 104-87-0 ]
  • 5-methyl-2,3-bis(4-methylphenyl)-1-indanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With methyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 50℃; for 24h;Sealed tube; To 25mL reactor were added <strong>[2789-88-0]1,2-bis(4-methylphenyl)acetylene</strong> (0.22mmol, 46mg), 4-methylbenzaldehyde (0.2mmol, 22μL), methyl trifluoromethanesulfonate (0.04mmol, 4.6μL), finally adding 0.5mL 1,2-dichloroethane as solvent, sealed reactor, 50 deg. C for 24 hours. After the reaction system was cooled, was added 15mL of water and 15mL of methylene chloride then stirred for 30min, extracted three times with 15mL of dichloromethane, the organic phases combined. The organic phase was washed with saturated brine, and finally dried over anhydrous magnesium sulfate 0.5h, after filtration the organic phase was rotary evaporated to give the crude product. The crude product with petroleum ether: ethyl acetate = 25: 1 (volume ratio) as eluent, 200 to 300 mesh silica gel adsorption phase column chromatography, to obtain a purity greater than 99% of the product as a yellow liquid 5-methyl-2,3-bis(4-methylphenyl)-1-indanone 49mg, yield 75%.
  • 85
  • [ 2789-88-0 ]
  • [ 34801-22-4 ]
  • C42H30 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate; In tetrahydrofuran; at 120℃; for 12h;Schlenk technique; Inert atmosphere; General procedure: A 25 mL Schlenk-type tube (with a Teflon high pressure valve and side arm) was charged withcompound 1a (34.6 mg, 0.10 mmol), alkynes (0.20 mmol), Cu(OAc)2.H2O (5.0 mg, 0.025 mmol),[RuCl2(p-cymene)]2 (6.1 mg, 0.01 mmol), AgSbF6 (13.7 mg, 0.04 mmol) and THF (1 mL). Thereaction tube was evacuated and back-filled with N2 (3 times, ballon). After the reaction mixturewas stirred at 120 oC for 12 h, it was allowed to cool down to room temperature. The reactionmixture was diluted with ethyl acetate (20 mL), and then filtered through a pad of Celite. Thefiltrate was washed with brine (10 mL), dried over Na2SO4, and concentrated in vacuo. Theresidue was purified by silica gel preparative TLC to give the corresponding products
Same Skeleton Products
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