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[ CAS No. 17873-01-7 ] {[proInfo.proName]}

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Chemical Structure| 17873-01-7
Chemical Structure| 17873-01-7
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Product Details of [ 17873-01-7 ]

CAS No. :17873-01-7 MDL No. :MFCD00048020
Formula : C10H16O3Si Boiling Point : -
Linear Structure Formula :- InChI Key :XQEGZYAXBCFSBS-UHFFFAOYSA-N
M.W : 212.32 Pubchem ID :2760672
Synonyms :

Safety of [ 17873-01-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17873-01-7 ]

* 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 [ 17873-01-7 ]

[ 17873-01-7 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 14371-10-9 ]
  • [ 17873-01-7 ]
  • [ 92804-29-0 ]
YieldReaction ConditionsOperation in experiment
85% With tetrabutyl ammonium fluoride; antimony(III) chloride; acetic acid In acetonitrile at 60℃; for 24h;
  • 2
  • [ 5153-67-3 ]
  • [ 17873-01-7 ]
  • [ 1882-47-9 ]
YieldReaction ConditionsOperation in experiment
54% With tetrabutyl ammonium fluoride; antimony(III) chloride; acetic acid In acetonitrile at 60℃; for 24h;
  • 3
  • (E)-1-phenyl-2-buten-1-one [ No CAS ]
  • [ 17873-01-7 ]
  • [ 62557-95-3 ]
YieldReaction ConditionsOperation in experiment
47% With tetrabutyl ammonium fluoride; antimony(III) chloride; acetic acid In acetonitrile at 60℃; for 34h;
  • 4
  • [ 18402-83-0 ]
  • [ 17873-01-7 ]
  • [ 182482-48-0 ]
YieldReaction ConditionsOperation in experiment
81% In 1,4-dioxane; water at 95℃; for 23h;
  • 5
  • [ 626-55-1 ]
  • [ 17873-01-7 ]
  • [ 4423-09-0 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide at 135℃; for 24h;
81% With sodium hydroxide at 60℃; for 9h;
71% With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation; Sealed tube;
71% With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation;

  • 6
  • [ 108-86-1 ]
  • [ 17873-01-7 ]
  • [ 644-08-6 ]
YieldReaction ConditionsOperation in experiment
96% With N-methyliminodiacetic acid; sodium fluoride; potassium hydroxide; palladium dichloride In water; isopropyl alcohol at 80℃; for 6h;
86% With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 4h;
73% With sodium hydroxide at 60℃; for 8h;
68 %Spectr. With tetrabutyl-ammonium chloride; sodium hydroxide In water at 80℃; for 3h; General Procedure for Hiyama Coupling Reaction (Table 1) General procedure: To a screw-capped vial with a stirring bar were added 4-bromotoluene(86.4 mg, 0.5 mmol), phenyltrimethoxysilane (152 mg,0.75 mmol), PS-PdONPs (2.9 mg, 1.5 mol% of Pd), TBAC (142 mg,0.5 mmol), and aq NaOH solution (1.5 M, 1 mL). After stirring at80 °C for 3 h, the reaction mixture was cooled to r.t. by immediatelyimmersing the vial in H2O (ca. 20 °C) for about 10 min.After separating the catalyst and the aqueous phase by centrifugation,the aqueous phase was decanted. The recovered catalystwas washed with H2O (5 × 3.0 mL) and Et2O (5 × 3.0 mL), whichwere then added to the aqueous phase. The aqueous phase wasextracted eight times with Et2O. The combined organic extractswere dried over MgSO4 and concentrated under reduced pressure.The product was analyzed by 1H NMR. The recovered catalystwas dried in vacuo and reused. Furthermore, the amount ofPd metal in the aqueous phase determined by ICP-AES analysiswas <0.1 ppm.

  • 7
  • [ 104-92-7 ]
  • [ 17873-01-7 ]
  • [ 53040-92-9 ]
YieldReaction ConditionsOperation in experiment
83% With tetrabutyl ammonium fluoride; tris-(o-tolyl)phosphine at 80℃; for 0.75h;
78% With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation; Sealed tube;
78% With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation;
70% With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 4h;
62% With N-methyliminodiacetic acid; sodium fluoride; potassium hydroxide; palladium dichloride In water; isopropyl alcohol at 80℃; for 12h;

  • 9
  • [ 17873-01-7 ]
  • [ 100-00-5 ]
  • [ 2143-88-6 ]
YieldReaction ConditionsOperation in experiment
98% With tetrabutyl ammonium fluoride; tris-(o-tolyl)phosphine at 80℃; for 0.666667h;
88% With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 12h;
84% With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; 2.2. General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4.
  • 10
  • [ 17873-01-7 ]
  • [ 586-78-7 ]
  • [ 2143-88-6 ]
YieldReaction ConditionsOperation in experiment
95% With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 4h;
90% With sodium hydroxide at 60℃; for 2h;
  • 11
  • [ 917086-20-5 ]
  • [ 17873-01-7 ]
  • (2R,7aS)-2-(4-Methyl-benzyl)-hexahydro-pyrrolizin-3-one [ No CAS ]
  • (2S,7S)-2-(4-methylbenzyl)-hexahydropyrrolizin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In 1,4-dioxane; water at 110℃; for 24h;
  • 12
  • [ 930-68-7 ]
  • [ 17873-01-7 ]
  • [ 99495-15-5 ]
YieldReaction ConditionsOperation in experiment
91% With tetrakis(actonitrile)copper(I) hexafluorophosphate; water at 120℃; for 4h; microwave irradiation;
  • 13
  • [ 51-17-2 ]
  • [ 17873-01-7 ]
  • [ 60057-83-2 ]
YieldReaction ConditionsOperation in experiment
93% With tetrabutyl ammonium fluoride; iron(III) chloride; copper at 50℃; for 24h;
  • 14
  • [ 288-32-4 ]
  • [ 17873-01-7 ]
  • [ 25372-10-5 ]
YieldReaction ConditionsOperation in experiment
58% With tetrabutyl ammonium fluoride; iron(III) chloride; copper at 50℃; for 24h;
  • 15
  • [ 288-88-0 ]
  • [ 17873-01-7 ]
  • [ 2244-88-4 ]
YieldReaction ConditionsOperation in experiment
96% With tetrabutyl ammonium fluoride; iron(III) chloride; copper at 50℃; for 24h;
  • 16
  • [ 288-36-8 ]
  • [ 17873-01-7 ]
  • [ 20320-18-7 ]
YieldReaction ConditionsOperation in experiment
57% With tetrabutyl ammonium fluoride; iron(III) chloride; copper at 50℃; for 24h;
  • 17
  • 6Pd(2+)*6(C5H4N)2*4C3N3(C5H4N)3*12NO3(1-)=Pd6((C5H4N)2)6(C3N3(C5H4N)3)4(NO3)12 [ No CAS ]
  • [ 17873-01-7 ]
  • 6Pd(2+)*6C10N2H8*4C3N3(C5NH4)3*12NO3(1-)*(SiOOHC6H4CH3)3=(Pd(C5H4N)4)6(C3N3)4(NO3)12*(SiOOHC6H4CH3)3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In water silan suspended in aq. soln. of host at 100 °C, mixt. stirred for100 °C for 1 h; mixt. cooled to room temp., soln. filtered, evapd., product recrystd. from H2O; detnd. by XRD, NMR;
  • 18
  • [ 1016624-90-0 ]
  • [ 17873-01-7 ]
  • [ 1016627-44-3 ]
  • [ 1016627-28-3 ]
YieldReaction ConditionsOperation in experiment
With (1,2-dimethoxyethane)dichloronickel(II) In 1,4-dioxane at 20℃; for 16h; Title compound not separated from byproducts.;
With (1,2-dimethoxyethane)dichloronickel(II) In 1,4-dioxane at 20℃; for 16h; Title compound not separated from byproducts.;
  • 19
  • C17H19O4SN [ No CAS ]
  • [ 17873-01-7 ]
  • 4-(4'-methylbiphenyl-3-yl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere;
  • 20
  • [ 15161-04-3 ]
  • [ 17873-01-7 ]
  • [ 27331-34-6 ]
YieldReaction ConditionsOperation in experiment
63% With dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere;
  • 21
  • [ 7385-85-5 ]
  • [ 17873-01-7 ]
  • [ 59115-49-0 ]
YieldReaction ConditionsOperation in experiment
78% With dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere;
  • 22
  • [ 17873-01-7 ]
  • [ 536-74-3 ]
  • [ 3287-02-3 ]
YieldReaction ConditionsOperation in experiment
90% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; silver fluoride; sodium hydrogencarbonate In acetonitrile at 20℃; for 3h;
  • 23
  • [ 52843-75-1 ]
  • [ 17873-01-7 ]
  • [ 4423-09-0 ]
YieldReaction ConditionsOperation in experiment
40% With tetrabutyl ammonium fluoride; palladium diacetate; XPhos In tetrahydrofuran; <i>tert</i>-butyl alcohol at 90℃; Inert atmosphere;
  • 24
  • [ 17873-01-7 ]
  • [ 52200-03-0 ]
  • [ 24423-07-2 ]
YieldReaction ConditionsOperation in experiment
96% With tetrabutyl ammonium fluoride; palladium diacetate; XPhos In tetrahydrofuran; <i>tert</i>-butyl alcohol at 90℃; Inert atmosphere;
  • 25
  • [ 17873-01-7 ]
  • [ 59970-38-6 ]
  • 1-(4-tert-butylphenyl)-4-methylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; tetrabutyl ammonium fluoride; palladium diacetate; acetic acid In <i>tert</i>-butyl alcohol at 90℃; for 16h; Inert atmosphere;
71% With tetrabutyl ammonium fluoride; palladium diacetate; XPhos In tetrahydrofuran; <i>tert</i>-butyl alcohol at 90℃; Inert atmosphere;
  • 26
  • [ 1070731-22-4 ]
  • [ 17873-01-7 ]
  • [ 7383-87-1 ]
YieldReaction ConditionsOperation in experiment
84% With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; tetrabutyl ammonium fluoride; palladium diacetate; acetic acid In <i>tert</i>-butyl alcohol at 90℃; for 16h; Inert atmosphere;
  • 27
  • [ 10290-91-2 ]
  • [ 17873-01-7 ]
  • [ 59115-49-0 ]
YieldReaction ConditionsOperation in experiment
71% With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; tetrabutyl ammonium fluoride; palladium diacetate; acetic acid In <i>tert</i>-butyl alcohol at 90℃; for 16h; Inert atmosphere;
  • 28
  • [ 13141-42-9 ]
  • [ 17873-01-7 ]
  • C20H17N [ No CAS ]
  • C20H17N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(2-phenylethynyl)pyridine; (4-methylphenyl)trimethoxysilane With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrabutyl ammonium fluoride; copper diacetate; triphenylphosphine In toluene at 20℃; for 2h; Stage #2: With water In toluene at 110℃; for 12h; regioselective reaction;
  • 29
  • [ 1129-65-3 ]
  • [ 17873-01-7 ]
  • C19H22 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: (hex-1-yn-1-yl)benzene; (4-methylphenyl)trimethoxysilane With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrabutyl ammonium fluoride; copper diacetate; triphenylphosphine In toluene at 20℃; for 2h; Stage #2: With water In toluene at 110℃; for 12h; regioselective reaction;
  • 30
  • [ 17873-01-7 ]
  • [ 501-65-5 ]
  • [ 70603-14-4 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: (4-methylphenyl)trimethoxysilane; diphenyl acetylene With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrabutyl ammonium fluoride; copper diacetate; triphenylphosphine In toluene at 20℃; for 2h; Stage #2: With water In toluene at 110℃; for 12h;
  • 31
  • 5-chloro-1-(4-methoxybenzyl)-3-(phenylsulfanyl)pyrazin-2(1H)-one [ No CAS ]
  • [ 17873-01-7 ]
  • 5-chloro-3-(4-methylphenyl)-1-(4-methoxybenzyl)-2(1H)-pyrazinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 2h; Inert atmosphere;
  • 32
  • [ 17873-01-7 ]
  • [ 62-53-3 ]
  • [ 620-84-8 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: (4-methylphenyl)trimethoxysilane With tetrabutyl ammonium fluoride; copper diacetate; tris(pentafluorophenyl)phosphine In dichloromethane; water at 20℃; for 0.0833333h; Molecular sieve; Stage #2: aniline With oxygen In dichloromethane; water at 20℃; for 24h;
  • 33
  • [ 109-09-1 ]
  • [ 17873-01-7 ]
  • [ 4467-06-5 ]
YieldReaction ConditionsOperation in experiment
83% With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 2h; Inert atmosphere; Neat (no solvent);
  • 34
  • [ 2398-37-0 ]
  • [ 17873-01-7 ]
  • [ 24423-07-2 ]
YieldReaction ConditionsOperation in experiment
91% With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 3h; Inert atmosphere; Neat (no solvent);
  • 35
  • [ 623-12-1 ]
  • [ 17873-01-7 ]
  • [ 53040-92-9 ]
YieldReaction ConditionsOperation in experiment
82% With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 2h; Inert atmosphere; Neat (no solvent);
82% With 3-(dicyclohexylphosphino)-2-(2-methoxyphenyl)-1-methyl-1-H-indole; tetrabutyl ammonium fluoride; palladium diacetate at 110℃; for 3h; Schlenk technique; Inert atmosphere; Sealed tube;
  • 36
  • [ 98-81-7 ]
  • [ 17873-01-7 ]
  • [ 948-55-0 ]
YieldReaction ConditionsOperation in experiment
78% With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 1h; Inert atmosphere; Neat (no solvent);
  • 37
  • [ 586-77-6 ]
  • [ 17873-01-7 ]
  • [ 141082-00-0 ]
YieldReaction ConditionsOperation in experiment
71% With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate In 1,4-dioxane at 80℃; for 5h; Inert atmosphere;
  • 38
  • [ 603-76-9 ]
  • [ 17873-01-7 ]
  • [ 51358-08-8 ]
YieldReaction ConditionsOperation in experiment
81% With tetrabutyl ammonium fluoride; palladium diacetate; acetic acid; silver(l) oxide In tetrahydrofuran; ethanol at 20℃; Inert atmosphere; regioselective reaction;
  • 39
  • [ 930-68-7 ]
  • [ 17873-01-7 ]
  • [ 6330-12-7 ]
YieldReaction ConditionsOperation in experiment
82% With 1,10-Phenanthroline; palladium diacetate; silver fluoride In N,N-dimethyl-formamide at 60℃;
  • 40
  • [ 1008-89-5 ]
  • [ 17873-01-7 ]
  • 2-[4’-methyl-(1,1’-biphenyl)-2-yl]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With palladium diacetate; silver fluoride; p-benzoquinone In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; seal tube;
67 %Chromat. With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In 1,2-dichloro-ethane at 140℃; for 20h; Inert atmosphere;
  • 41
  • [ 17873-01-7 ]
  • [ 106-49-0 ]
  • [ 613-33-2 ]
YieldReaction ConditionsOperation in experiment
General procedure: The concentration of0.25mol aniline was dissolved in the mixture of 63 ml HCl and 63 ml water in600 ml beaker. After cooled to 0-5 oC with stirring, anilinehydrochloride crystallization. Aqueous solution of sodium nitrite (18gdissolved in 40 ml water) was added into beaker dropwise with stirring, keepingthe temperature under 5 oC. 40 g of sodium tetrafluoroboratesolution dissolved in 80 ml water was added to the diazonium salt solution, andthen continue to stir for 10 minutes. The solid was immediately washed by 10 ml5 % solution of sodium tetrafluoroborate for three times after filtered, andthen washed by 15 ml methanol twice to afford diazonium salt.A mixture of arenediazonium tetrafluoroborate salt(0.5 mmol), Pd(OAc)2 (5 mol%), TBAF (0.5 mmol) and aryl silanes (0.6mmol) was stirred in water (1 mL) at room termperature for 6 h. Afterwards, thereaction solution was filtered through a filter paper and the solution wasextracted by Et2O (1 mL) for three times. The organic phase wascombined and evaporated under reduced pressure. The residue was purified on aSiO2 column to afford the desired product.
  • 42
  • [ 141-32-2 ]
  • [ 17873-01-7 ]
  • [ 123248-21-5 ]
YieldReaction ConditionsOperation in experiment
70% With tetrabutyl ammonium fluoride; p-benzoquinone In tetrahydrofuran at 40℃; for 14h;
60% With C14H16N6; palladium diacetate; silver fluoride In N,N-dimethyl acetamide at 60℃; for 24h; 4.3. General procedure of palladium-catalyzed Mizoroki-Heck type reaction with aryl trialkoxysilanesCommentComment General procedure: To a mixture of olefin (0.5 mmol), AgF (0.191 mg, 1.5 mmol), Pd(OAc)2 (5.6 mg, 25 μmol), and ligand 1e (6.7 mg, 25 μmol) in DMAc (1.0 mL) was added aryl trialkoxysilane (1.0 mmol) at room temperature under an atmosphere of air. The mixture was stirred at 60 °C. After 24 h, the mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane or hexane/EtOAc=100 to 10/1).
  • 43
  • [ 17873-01-7 ]
  • [ 99-90-1 ]
  • [ 5748-38-9 ]
YieldReaction ConditionsOperation in experiment
46% With 3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazolium chloride; water; palladium diacetate; sodium hydroxide at 120℃; for 1h; Microwave irradiation;
  • 44
  • [ 623-03-0 ]
  • [ 17873-01-7 ]
  • [ 50670-50-3 ]
YieldReaction ConditionsOperation in experiment
81% With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; 2.2. General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4.
  • 45
  • [ 1126-46-1 ]
  • [ 17873-01-7 ]
  • [ 49742-56-5 ]
YieldReaction ConditionsOperation in experiment
79% With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; 2.2. General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4.
  • 46
  • [ 17873-01-7 ]
  • [ 99-91-2 ]
  • [ 5748-38-9 ]
YieldReaction ConditionsOperation in experiment
73% With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; 2.2. General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4.
  • 47
  • [ 624-31-7 ]
  • [ 17873-01-7 ]
  • [ 613-33-2 ]
YieldReaction ConditionsOperation in experiment
80% With tetrabutyl ammonium fluoride; In water; toluene; at 100℃; for 20h; General procedure: Catalyst 1a22a (43 mg, 0.1 mol % of supported palladium) was added to a solution of aryl iodide (0.40 mmol, 1.0 equiv), aryltrialkoxysilane (0.80 mmol, 2.0 equiv), TBAF·3H2O (252 mg, 0.8 mmol, 2.0 equiv) in a mixture of toluene (5 mL) and H2O (50 muL). The reaction mixture was heated at 100 C for 20 h. After cooling to rt, 1a was filtered under vacuum on a 0.2 mum membrane. The catalyst was successively washed with toluene (10 mL) and Et2O (10 mL). The combined organic phases were washed with H2O (20 mL), dried with MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash-chromatography on silica gel. Catalyst 1a was dried under vacuum and can directly be used for another Hiyama coupling.
  • 48
  • AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) [ No CAS ]
  • [ 17873-01-7 ]
  • [N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](4-tolyldimethoxysilanolate)gold(I) [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With air In toluene at 20℃; for 1h; Inert atmosphere;
  • 49
  • AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) [ No CAS ]
  • [ 17873-01-7 ]
  • (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(p-methylphenyl)gold [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In 1,4-dioxane at 110℃; for 0.8h; Inert atmosphere;
  • 50
  • [ 17873-01-7 ]
  • [ 824-79-3 ]
  • [ 613-33-2 ]
  • 51
  • [ 17873-01-7 ]
  • [ 613-33-2 ]
  • 52
  • [ 3972-65-4 ]
  • [ 17873-01-7 ]
  • 1-(4-tert-butylphenyl)-4-methylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation; Sealed tube;
80% With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation;
  • 53
  • [ 95-46-5 ]
  • [ 17873-01-7 ]
  • [ 611-61-0 ]
YieldReaction ConditionsOperation in experiment
82% With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation; Sealed tube;
82% With N-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]aniline; tetrabutylammomium bromide; palladium diacetate; sodium hydroxide In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation;
  • 54
  • [ 1483-82-5 ]
  • [ 17873-01-7 ]
  • [ 3287-02-3 ]
YieldReaction ConditionsOperation in experiment
90% With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; Synthesis of internal alkynes (3-12); general procedure General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product.
  • 55
  • [ 932-88-7 ]
  • [ 17873-01-7 ]
  • [ 886-66-8 ]
  • [ 3287-02-3 ]
YieldReaction ConditionsOperation in experiment
1: 40% 2: 33 %Chromat. With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; Synthesis of internal alkynes (3-12); general procedure General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product.
  • 56
  • [ 19821-84-2 ]
  • [ 17873-01-7 ]
  • [ 121866-33-9 ]
YieldReaction ConditionsOperation in experiment
44% With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; Synthesis of internal alkynes (3-12); general procedure General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product.
  • 57
  • [ 17873-01-7 ]
  • [ 932-87-6 ]
  • [ 3287-02-3 ]
YieldReaction ConditionsOperation in experiment
83% With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; Synthesis of internal alkynes (3-12); general procedure General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product.
  • 58
  • [ 17873-01-7 ]
  • [ 98-09-9 ]
  • [ 644-08-6 ]
YieldReaction ConditionsOperation in experiment
87% With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl ammonium fluoride In N,N-dimethyl-formamide; acetonitrile at 100℃; for 3h; Inert atmosphere; Green chemistry;
  • 59
  • [ 570-02-5 ]
  • [ 17873-01-7 ]
  • [ 1040196-63-1 ]
YieldReaction ConditionsOperation in experiment
57% With palladium(II) trifluoroacetate; C30H30N4; silver fluoride; In N,N-dimethyl acetamide; at 100℃; for 2h; General procedure: To a mixture of aryl(trialkoxy)silane(0.20 mmol), AgF (76.6 mg, 0.60 mmol), Pd(TFA)2 (5.0 mg, 0.015 mmol,7.5 mol %), and ligand 1g (6.7 mg, 0.015 mmol, 7.5 mol %) in DMAc (1.0 mL)was added arylcarboxylic acid (0.40 mmol) at room temperature under an atmosphere of air. After the mixture was stirred at 100?or 110?C for 2-8 h, the mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/EtOAc = 20:1).
  • 60
  • [ 106-37-6 ]
  • [ 17873-01-7 ]
  • [ 97295-31-3 ]
YieldReaction ConditionsOperation in experiment
With 2% active carbon-supported palladium; sodium hydroxide In water at 100℃;
  • 61
  • [ 626-39-1 ]
  • [ 17873-01-7 ]
  • [ 50446-43-0 ]
  • 62
  • S-methyl-S-(p-tolyl)sulfoximine [ No CAS ]
  • [ 17873-01-7 ]
  • N-(4-methylphenyl)-S,S-(4-methylphenyl)(methyl)sulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;
  • 63
  • [ 17873-01-7 ]
  • [ 77970-95-7 ]
  • (4-methoxyphenyl)(methyl)(p-tolylimino)-λ6-sulfanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;
  • 64
  • [ 22133-00-2 ]
  • [ 17873-01-7 ]
  • N-(4-methyl)phenyl-S-(3-chloro)phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;
  • 65
  • [ 17873-01-7 ]
  • [ 4381-25-3 ]
  • rac-N-[(4-methyl)-phenyl]-S-phenyl-S-methylsulfoximine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;
  • 66
  • C11H16FO4P [ No CAS ]
  • [ 17873-01-7 ]
  • [ 1352918-73-0 ]
YieldReaction ConditionsOperation in experiment
94% With 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere; Hiyama Cross-Coupling; General Procedure: General procedure: An oven dried Schlenk tube with Pd(OAc)2 (5 mol%) and dppp (10 mol%) was evacuated and purged with argon three times. A mixture of TBAF (1 M in THF, 0.36 mL), 2a (0.45 mmol), and benzylic phosphate (1a; 0.30 mmol) was dissolved in freshly distilled 1,4-dioxane (1.0 mL), and added at r.t. The reaction mixture was heated with stirring at 100 °C for 24 h, then cooled to ambient temperature and transferred to around-bottom flask. Silica gel (2.0 g) was added and the solvent was removed under reduced pressure to afford a free flowing powder. The powder was then dry-loaded onto a silica gel column and purified by flash chromatography using petroleum as the eluent to give the desired product 3aa.
  • 67
  • [ 17873-01-7 ]
  • [ 128732-38-7 ]
  • 1-(4-methylbenzyl)-3-(trifluoromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere; Hiyama Cross-Coupling; General Procedure: General procedure: An oven dried Schlenk tube with Pd(OAc)2 (5 mol%) and dppp (10 mol%) was evacuated and purged with argon three times. A mixture of TBAF (1 M in THF, 0.36 mL), 2a (0.45 mmol), and benzylic phosphate (1a; 0.30 mmol) was dissolved in freshly distilled 1,4-dioxane (1.0 mL), and added at r.t. The reaction mixture was heated with stirring at 100 °C for 24 h, then cooled to ambient temperature and transferred to around-bottom flask. Silica gel (2.0 g) was added and the solvent was removed under reduced pressure to afford a free flowing powder. The powder was then dry-loaded onto a silica gel column and purified by flash chromatography using petroleum as the eluent to give the desired product 3aa.
  • 68
  • [ 7145-06-4 ]
  • [ 17873-01-7 ]
  • [ 21895-16-9 ]
YieldReaction ConditionsOperation in experiment
95% With 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere; Hiyama Cross-Coupling; General Procedure: General procedure: An oven dried Schlenk tube with Pd(OAc)2 (5 mol%) and dppp (10 mol%) was evacuated and purged with argon three times. A mixture of TBAF (1 M in THF, 0.36 mL), 2a (0.45 mmol), and benzylic phosphate (1a; 0.30 mmol) was dissolved in freshly distilled 1,4-dioxane (1.0 mL), and added at r.t. The reaction mixture was heated with stirring at 100 °C for 24 h, then cooled to ambient temperature and transferred to around-bottom flask. Silica gel (2.0 g) was added and the solvent was removed under reduced pressure to afford a free flowing powder. The powder was then dry-loaded onto a silica gel column and purified by flash chromatography using petroleum as the eluent to give the desired product 3aa.
  • 69
  • [ 1428524-92-8 ]
  • [ 17873-01-7 ]
  • ethyl 2-(pyridin-3-yl)-2-(p-tolyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With [Rh(OH)(cod)]2; tetrabutyl ammonium fluoride; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 5h; Inert atmosphere;
  • 70
  • [ 17873-01-7 ]
  • [ 72410-67-4 ]
  • tert-butyl 2-phenyl-2-(p-tolyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With [Rh(OH)(cod)]2; tetrabutyl ammonium fluoride; tricyclohexylphosphine tetrafluoroborate In tetrahydrofuran; water at 80℃; for 5h; Inert atmosphere;
  • 71
  • [ 170891-76-6 ]
  • [ 17873-01-7 ]
  • 2,2-dimethyl-N-(quinolin-8-yl)-3-(p-tolyloxy)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With di-<i>tert</i>-butyl dicarbonate; copper diacetate; sodium pivalate; cesium fluoride; silver(l) oxide In N,N-dimethyl-formamide at 150℃; for 0.5h; Sealed tube; Inert atmosphere; regioselective reaction;
  • 72
  • [ 17873-01-7 ]
  • [ 15163-59-4 ]
  • [ 70680-21-6 ]
YieldReaction ConditionsOperation in experiment
93% With copper (II)-fluoride; [Pd(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(naphthoquinone)]2; silver carbonate In N,N-dimethyl acetamide at 130℃; for 19h; Inert atmosphere; Sealed tube; Glovebox;
  • 73
  • [ 591-50-4 ]
  • [ 17873-01-7 ]
  • [ 644-08-6 ]
YieldReaction ConditionsOperation in experiment
83% With potassium fluoride; tetra-(n-butyl)ammonium iodide In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; General Procedure for Hiyama Cross-Coupling Reactions. General procedure: A typical procedure for the cross-coupling reaction using the nanocrystals is as follows: degassed N,N'-dimethylacetamide (DMA) (1.0 mL), aryl halide (0.5 mmol), trimethoxyphenylsilane (1.5 mmol), KF (1.5 mmol), tetrabutylammonium iodide (TBAI) (0.1 mmol), and Pd-Fe3O4 catalyst (1 mol%) were added to a vial, which was equipped with a magnetic bar and purged with argon gas. The vial was sealed and the reaction mixture was heated to 150 °C for 16 h with vigorous stirring. After the reaction, the mixture was cooled to room temperature and the catalyst was collected using an external magnet. The solution containing products was diluted and extracted between dichloromethane (10 mL) and H2O(10 mL). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography using a 1:6 mixture of ethyl acetate and n-hexane as an eluent to furnish the desired products.
  • 74
  • [ 3389-54-6 ]
  • [ 17873-01-7 ]
  • (4'-methyl-[1,1'-biphenyl]-2-yl)(pyrrolidin-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In tetrahydrofuran at 140℃; for 20h;
  • 75
  • [ 221044-05-9 ]
  • [ 17873-01-7 ]
  • [ 1608124-60-2 ]
YieldReaction ConditionsOperation in experiment
87% With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water at 140℃; for 20h; Inert atmosphere; Green chemistry;
71% With copper (II)-fluoride; oxygen; cobalt(III) acetylacetonate In toluene at 160℃; for 24h; Sealed tube;
  • 76
  • [ 17873-01-7 ]
  • diethyl 2,2′-disulfanediylbis(6-methyl-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate) [ No CAS ]
  • [ 1048007-29-9 ]
YieldReaction ConditionsOperation in experiment
70% With copper(I) thiophene-2-carboxylate; tetrabutyl ammonium fluoride; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 60℃; for 24h; Sealed tube; Schlenk technique; Inert atmosphere; 2.2 General Procedure for synthesis 3a-6c. General procedure: Disulfide 1a (0.2 mmol, 0.1094 g), Pd(OAc)2 (3 mol %), CuTC (3.0 equiv), PCy3 (6 mol %), was added respectively to the sealed Schlenktube, Then phenyltrimethoxysilane 2a (3.0 equiv, 0.6 mmol, 0.1188 g), TBAF (3.0 equiv, 0.6 mmol) and solvent THF (2 mL) was injectedinto the sealed tube by syringe in the presence of nitrogen. The mixture was stirred at 60 °C for 24 h. And the progress of the reaction wasmonitored by thin-layer chromatography (silica gel). After completion of the reaction, mixture was cooled to ambient temperature,quenched by addition of saturated NH4Cl (2 mL), and extracted with ethyl acetate (3×10 mL). The organic layers were combined and driedwith anhydrous MgSO4 and concentrated in vacuo, the resulting residue was purified by silica gel column chromatography using ethylacetate/petroleum ether (1:50) as eluent to afford the products (3a-6c).
  • 77
  • [ 67-56-1 ]
  • [ 931-70-4 ]
  • [ 17873-01-7 ]
YieldReaction ConditionsOperation in experiment
93% With graphene immobilized iridium complex containing N-heterocyclic carbene ligand functionalized with pyrene at 30℃; for 0.333333h;
  • 78
  • [ 7188-38-7 ]
  • [ 17873-01-7 ]
  • [ 62-53-3 ]
  • N-(tert-butyl)-4-methyl-N'-phenylbenzimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With potassium fluoride; copper diacetate; palladium dichloride In N,N-dimethyl-formamide at 120℃; for 24h;
  • 79
  • [ 201230-82-2 ]
  • [ 17873-01-7 ]
  • [ 62-53-3 ]
  • [ 6833-18-7 ]
YieldReaction ConditionsOperation in experiment
88% With copper (II)-fluoride; bis(triphenylphosphine)palladium(II) dichloride In acetonitrile at 80℃; for 24h; Schlenk technique;
88% With copper (II)-fluoride; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 80℃; for 24h; Sealed tube; 10 Preparation of 4-methyl-N-phenylbenzamide 0.75 mmol of p-methyl(trimethoxy)phenylsilane 10 mol% Pd(PPh3)Cl2 and 2equiv.CuF2 were dissolved in 3 mL CH3CN Shrek tube (with magnetic stirrer), and the reaction tube was closed from the reaction tube. The branch pipe is filled with carbon monoxide, filled with balloons and then emptied, three times, until the air is completely emptied, then the balloon is filled, then 0.5 mmol of aniline was added to the reaction tube, and the mixture was stirred under heating at 80 ° C for 24 hours. The reaction was monitored by TLC. After the reaction was completed, the mixture was extracted three times with 10 mL of ethyl acetate. 92.8 mg of a white solid compound was obtained in a yield of 88%.
  • 80
  • [ 1182669-71-1 ]
  • [ 17873-01-7 ]
  • 4′-methyl-3-methyl-N-(quinolin-8-yl)-[1,1′-biphenyl]-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With copper (II)-fluoride; cobalt(II) acetate; cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 20h; Schlenk technique; Inert atmosphere;
  • 81
  • [ 33757-48-1 ]
  • [ 17873-01-7 ]
  • 4'-methyl-N-(quinolin-8-yl)-[1,1'-biphenyl]-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With copper (II)-fluoride; cobalt(II) acetate; cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 20h; Schlenk technique; Inert atmosphere;
  • 82
  • [ 17873-01-7 ]
  • (1-fluoro-2,2-diiodovinyl)benzene [ No CAS ]
  • (Z)-1-(2-fluoro-2-phenylethenyl)-4-methylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 80℃; for 20h; regioselective reaction;
  • 83
  • [ 2441-97-6 ]
  • [ 17873-01-7 ]
  • (–)-(S)-3-(4-methylphenyl)cyclohexene [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; tetrabutyl ammonium fluoride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In tetrahydrofuran for 3h; Reflux; enantioselective reaction;
  • 84
  • [ 17873-01-7 ]
  • N-tert-butoxycarbonyl-5-chloro-3-piperidene [ No CAS ]
  • (–)-tert-butyl (S)-3-(p-tolyl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; tetrabutyl ammonium fluoride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In tetrahydrofuran for 3h; Reflux; enantioselective reaction;
  • 85
  • [ 1506-76-9 ]
  • [ 17873-01-7 ]
  • [ 121-44-8 ]
  • C126H90O24Si6(6-)*6C6H15N*6H(1+) [ No CAS ]
  • 86
  • [ 17873-01-7 ]
  • N,N,N-trimethyl-1-(4-cyanophenyl)methanaminium trifluoromethanesulfonate [ No CAS ]
  • [ 71947-05-2 ]
YieldReaction ConditionsOperation in experiment
97% With dichloro bis(acetonitrile) palladium(II); tetrabutyl ammonium fluoride; cyclohexyldiphenylphosphine In ethanol at 120℃; for 24h; Inert atmosphere; Schlenk technique;
  • 87
  • [ 573-57-9 ]
  • [ 17873-01-7 ]
  • [ 1505513-83-6 ]
  • (1R,2S)-2-(4-methylphenyl)-1,2-dihydronaphthalen-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
83 % ee With (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine); tris-(dibenzylideneacetone)dipalladium(0); CuF2*H2O In water; 1,2-dichloro-ethane at 20℃; Overall yield = 89 percent; Overall yield = 42.1 mg; enantioselective reaction;
Same Skeleton Products
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