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CAS No. : | 780-69-8 | MDL No. : | MFCD00009065 |
Formula : | C12H20O3Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JCVQKRGIASEUKR-UHFFFAOYSA-N |
M.W : | 240.37 | Pubchem ID : | 13075 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 67.1 |
TPSA : | 27.69 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.59 cm/s |
Log Po/w (iLOGP) : | 3.43 |
Log Po/w (XLOGP3) : | 3.06 |
Log Po/w (WLOGP) : | 1.94 |
Log Po/w (MLOGP) : | 1.26 |
Log Po/w (SILICOS-IT) : | 1.23 |
Consensus Log Po/w : | 2.18 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.07 |
Solubility : | 0.203 mg/ml ; 0.000844 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.31 |
Solubility : | 0.118 mg/ml ; 0.000492 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.11 |
Solubility : | 0.0189 mg/ml ; 0.0000785 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.95 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P260-P370+P378 | UN#: | 1993 |
Hazard Statements: | H225-H373-H412 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6 h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 molpercent), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium ethoxide In ethanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In tetrahydrofuran for 48h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methyl bottoms various compositions of methyl bottoms, various supply rates; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide In water at 120℃; for 3h; | |
87% | With N,N-bis(indolin-1-yl)ethane-1,2-diimine; tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 80℃; for 3h; | |
81% | With tetrabutyl ammonium fluoride; palladium diacetate; di(1-adamantyl)-N-butylphosphine hydroiodide at 80℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry; |
94 % Chromat. | With sodium hydroxide In 1,4-dioxane at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium hydroxide; cyclo-octa-1,5-diene In 1,4-dioxane at 90℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35-40 | With bromobenzene; magnesium In toluene byproducts: diphenyl; at 100°C;; | |
35-40 | With C6H5Br; Mg In toluene byproducts: diphenyl; at 100°C;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: bromochlorobenzene With [Pd{C6H2-(CH2CH2NH2)-(OMe)2-3,4}Br(PPh3)] In N,N-dimethyl-formamide at 100℃; for 0.0333333h; Microwave irradiation; | General procedure for the Hiyama reaction of aryl halides General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 °C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography. |
94% | Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: bromochlorobenzene With [Pd{C6H2(CH2CH2NH2)-(OMe)2-2,3}(μ-Br)]2 In N,N-dimethyl-formamide at 100℃; for 0.0833333h; Microwave irradiation; | |
94% | With sodium hydroxide In water at 80℃; for 3h; | 2.8 General Procedure for Hiyama Cross-CouplingReaction General procedure: To a stirring mixture of aryl halide (1 mmol), triethoxyphenylsilane(1.2 mmol) and NaOH (2 mmol) in H2O(4 mL),γ-Fe2O3-Pd-NHC-n-butyl-SO3Na (0.08 or 0.16 mol% based on Pd) was added. The resulting mixture was stirred at 80 °Cfor an appropriate time indicated by TLC monitoring. Aftercooling the reaction to room temperature, the catalyst wasseparated by an external magnet and washed with EtOAc.The product was extracted from the aqueous phase usingEtOAc (3 × 5 mL). After drying the combined organic layersover anhydrous Na2SO4,the solvent was evaporated togive the crude product. Purification of the crude product bycolumn chromatography on silica gel eluted with n-hexane:EtOAc = 30:1 produced the pure products (1-6). |
92% | Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Stage #2: bromochlorobenzene With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2 In N,N-dimethyl-formamide at 90℃; for 0.0333333h; Microwave irradiation; chemoselective reaction; | |
90% | With triethylamine In N,N-dimethyl-formamide at 90℃; for 3h; | |
88% | With sodium hydroxide In water at 120℃; for 36h; | |
87% | With sodium hydroxide In water at 90℃; for 3h; Green chemistry; | |
81% | With tetrabutyl ammonium fluoride; acetic acid In toluene at 100℃; for 24h; | |
99 %Chromat. | With [palladium(II) 1-(4-N,N’,N’’-trimethylbutylammonium)-4-(2-pyridyl)-1H-1,2,3-triazoledichloride]chloride; tetrabutylammomium bromide; sodium hydroxide In water at 120℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium hydroxide In water at 120℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With Pd((CH3)2C6H3NC(CH3)CHC(CH3)NC6H3(CH3)2)(CH3)(P(CH2CH3)3); tetrabutylammomium bromide; sodium hydroxide In water at 60℃; for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With Pd((CH3)2C6H3NC(CH3)CHC(CH3)NC6H3(CH3)2)(CH3)(P(CH2CH3)3); tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With Pd((CH3)2C6H3NC(CH3)CHC(CH3)NC6H3(CH3)2)(CH3)(P(CH2CH3)3); tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-bromobenzenecarbonitrile With [Pd{C6H2(CH2CH2NH2)-(OMe)2-2,3}(μ-Br)]2 In N,N-dimethyl-formamide at 100℃; for 0.0666667h; Microwave irradiation; | |
95% | Stage #1: triethoxyphenylsilane With cesium fluoride In 1-methyl-pyrrolidin-2-one at 20℃; for 1h; Stage #2: 4-bromobenzenecarbonitrile With (1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane)2Pd2Cl6 In 1-methyl-pyrrolidin-2-one at 20 - 100℃; for 0.0666667h; Microwave irradiation; | |
94% | Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Stage #2: 4-bromobenzenecarbonitrile With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2 In N,N-dimethyl-formamide at 90℃; for 0.0833333h; Microwave irradiation; |
93% | Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-bromobenzenecarbonitrile With [Pd{C6H2-(CH2CH2NH2)-(OMe)2-3,4}Br(PPh3)] In N,N-dimethyl-formamide at 100℃; for 0.0666667h; Microwave irradiation; | General procedure for the Hiyama reaction of aryl halides General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 °C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography. |
92% | With sodium hydroxide In water at 80℃; for 4.5h; | 2.8 General Procedure for Hiyama Cross-CouplingReaction General procedure: To a stirring mixture of aryl halide (1 mmol), triethoxyphenylsilane(1.2 mmol) and NaOH (2 mmol) in H2O(4 mL),γ-Fe2O3-Pd-NHC-n-butyl-SO3Na (0.08 or 0.16 mol% based on Pd) was added. The resulting mixture was stirred at 80 °Cfor an appropriate time indicated by TLC monitoring. Aftercooling the reaction to room temperature, the catalyst wasseparated by an external magnet and washed with EtOAc.The product was extracted from the aqueous phase usingEtOAc (3 × 5 mL). After drying the combined organic layersover anhydrous Na2SO4,the solvent was evaporated togive the crude product. Purification of the crude product bycolumn chromatography on silica gel eluted with n-hexane:EtOAc = 30:1 produced the pure products (1-6). |
90% | With sodium hydroxide In water at 90℃; for 2.5h; Green chemistry; | |
89% | With sodium hydroxide In ethanol at 25℃; for 3h; Irradiation; Sealed tube; Green chemistry; | |
87% | With triethylamine In N,N-dimethyl-formamide at 90℃; for 4h; | |
86% | With tetrabutyl ammonium fluoride In toluene at 90℃; for 9h; | |
85% | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; P(p-C6H4F)3 In toluene at 120℃; for 12h; Inert atmosphere; | |
85% | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; P(p-C6H4F)3 In water; toluene at 120℃; for 12h; Inert atmosphere; | |
71% | With tetrabutyl ammonium fluoride; acetic acid In toluene at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: triethoxyphenylsilane With cesium fluoride In 1-methyl-pyrrolidin-2-one at 20℃; for 1h; Stage #2: 1-(3-Bromophenyl)ethanone With (1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane)2Pd2Cl6 In 1-methyl-pyrrolidin-2-one at 20 - 100℃; for 0.166667h; Microwave irradiation; | |
83% | Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1-(3-Bromophenyl)ethanone With [Pd{C6H2-(CH2CH2NH2)-(OMe)2-3,4}Br(PPh3)] In N,N-dimethyl-formamide at 100℃; for 0.166667h; Microwave irradiation; | General procedure for the Hiyama reaction of aryl halides General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 °C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography. |
78% | Stage #1: triethoxyphenylsilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Stage #2: 1-(3-Bromophenyl)ethanone With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2 In N,N-dimethyl-formamide at 90℃; for 0.133333h; Microwave irradiation; |
49 %Spectr. | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; P(p-C6H4F)3 In water; toluene at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide In water at 80℃; for 6h; | 2.8 General Procedure for Hiyama Cross-CouplingReaction General procedure: To a stirring mixture of aryl halide (1 mmol), triethoxyphenylsilane(1.2 mmol) and NaOH (2 mmol) in H2O(4 mL),γ-Fe2O3-Pd-NHC-n-butyl-SO3Na (0.08 or 0.16 mol% based on Pd) was added. The resulting mixture was stirred at 80 °Cfor an appropriate time indicated by TLC monitoring. Aftercooling the reaction to room temperature, the catalyst wasseparated by an external magnet and washed with EtOAc.The product was extracted from the aqueous phase usingEtOAc (3 × 5 mL). After drying the combined organic layersover anhydrous Na2SO4,the solvent was evaporated togive the crude product. Purification of the crude product bycolumn chromatography on silica gel eluted with n-hexane:EtOAc = 30:1 produced the pure products (1-6). |
89% | With C58H78Cl4N6Pd2; tetrabutyl ammonium fluoride In toluene at 120℃; for 5h; | |
85% | With triethylamine In N,N-dimethyl-formamide at 90℃; for 4h; |
80% | With sodium hydroxide In water at 90℃; for 3.5h; Green chemistry; | |
80% | With sodium hydroxide In ethanol at 25℃; for 4.5h; Irradiation; Sealed tube; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tetrabutyl ammonium fluoride; palladium dichloride In tetrahydrofuran at 70℃; for 3h; |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride at 130℃; for 24h; Green chemistry; | General procedure for Hiyama coupling reactions General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 °C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information. |
58% | With copper(l) iodide; cesium fluoride; N,N-dimethyl-2-(diphenylphosphino)aniline In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With copper(l) iodide; cesium fluoride; N,N-dimethyl-2-(diphenylphosphino)aniline In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; | |
73 %Spectr. | With copper (II)-fluoride; [PdCl2(1,3-dimethyl-imidazol-2-ylidene)(AsPh3)] In N,N-dimethyl-formamide at 110℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; | ||
1: 70 %Spectr. 2: 14 %Spectr. | With copper (II)-fluoride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 110℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium hydroxide In ethanol at 25℃; for 1.5h; Irradiation; Sealed tube; Green chemistry; | |
96% | With sodium hydroxide In water at 80℃; for 2.5h; | 2.8 General Procedure for Hiyama Cross-CouplingReaction General procedure: To a stirring mixture of aryl halide (1 mmol), triethoxyphenylsilane(1.2 mmol) and NaOH (2 mmol) in H2O(4 mL),γ-Fe2O3-Pd-NHC-n-butyl-SO3Na (0.08 or 0.16 mol% based on Pd) was added. The resulting mixture was stirred at 80 °Cfor an appropriate time indicated by TLC monitoring. Aftercooling the reaction to room temperature, the catalyst wasseparated by an external magnet and washed with EtOAc.The product was extracted from the aqueous phase usingEtOAc (3 × 5 mL). After drying the combined organic layersover anhydrous Na2SO4,the solvent was evaporated togive the crude product. Purification of the crude product bycolumn chromatography on silica gel eluted with n-hexane:EtOAc = 30:1 produced the pure products (1-6). |
90% | With sodium hydroxide In water at 90℃; for 2h; Green chemistry; |
88% | With triethylamine In N,N-dimethyl-formamide at 90℃; for 3h; | |
48% | With copper(l) iodide; cesium fluoride; N,N-dimethyl-2-(diphenylphosphino)aniline In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; | |
48% | With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride at 130℃; for 24h; Green chemistry; | General procedure for Hiyama coupling reactions General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 °C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50℃; for 3h; | General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 molpercent) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50℃; for 3h; | General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50℃; for 3h; | General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h; | Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h; | Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50℃; for 3h; | General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h; | Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h; | Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With copper(II) fluoride dihydrate; palladium diacetate; trifluoroacetic acid In N,N-dimethyl acetamide at 100℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6h; | Typical procedure for carbonylative coupling with aryl iodines: General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6h; | Typical procedure for carbonylative coupling with aryl iodines: General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6h; | Typical procedure for carbonylative coupling with aryl iodines: General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h; | Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h; | Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h; | Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 100℃; under 760.051 Torr; for 6h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 100℃; under 760.051 Torr; for 6h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h; | Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 100℃; under 760.051 Torr; for 6h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h; | Typical procedure for carbonylative coupling with aryl bromides: General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 100℃; under 760.051 Torr; for 6h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper (II)-fluoride; palladium diacetate; cesium fluoride; p-benzoquinone; 4,4'-di-tert-butyl-2,2'-bipyridine In dimethyl sulfoxide at 150℃; for 5h; Molecular sieve; Inert atmosphere; | 58 Example 56-60 In the 5mL reactor, replace it with argon three times, then add 1mm magnets,P-methoxycinnamic acid (0.4 mmol), catalyst Pd(OAc) 2 (0.04 mmol),CuF2 oxidant (0.6 mmol), ligand L7 (0.06 mmol),1 equivalent of cesium fluoride (0.4 mmol), 1 equivalent of p-benzoquinone (BQ, 0.4 mmol),75 mg molecular sieve (water removal), the reactor was evacuated and replaced with argon three times.Then, phenyltriethoxysilane (0.8 mmol) and DMSO (2 ml) were mixed and added to the reactor, and then an argon balloon was inserted, and then the reactor was placed in an oil bath previously heated to 150 ° C. The reaction is carried out at different temperatures for different times. After the reaction is over,The reaction solution was filtered through celite, and the filtrate was thThe aqueous phase is back extracted twice with ethyl acetate or dichloromethane, then the organic phases are combined.It was dried over anhydrous magnesium sulfate. The dried organic phase was spun on a vacuum rotary evaporator.The objective product was isolated by chromatography on a thin layer of silica gel, and yield was calculated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With [Ni2(1,3-diisopropyl-imidazolin-2-ylidene)4(μ-1,5-cyclooctadiene)] In toluene at 110℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride; at 130℃; for 24h;Green chemistry; | General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride; at 130℃; for 24h;Green chemistry; | General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With bis-triphenylphosphine-palladium(II) chloride; tetrabutylphosphonium 4-ethoxyvalerate; tetrabutyl ammonium fluoride at 130℃; for 24h; Green chemistry; | General procedure for Hiyama coupling reactions General procedure: In a 4 mL screw-cap vial, 0.5 mmol of the corresponding iodoarene compounds, 1.5 eq of the corresponding silane, 1.5 eq of tetrabutylammonium fluoride (TBAF), 0.01 eq PdCl2(PPh3)2, and 0.8 mL of tetrabutylphosphonium 4-ethoxyvalerate ([TBP][4EtOV]) ionic liquid were mixed and stirred at 130 °C for 24 h. After cooling, the mixture was partitioned between 5 mL of 1 M HCl and 5 mL of pentane. The aqueous phase was extracted subsequently with 3 * 5 mL of pentane. The combined organic phase was washed with brine, dried over MgSO4, and filtered, and the solvent was evaporated under reduced pressure (ca. 1.333 kPa). The residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063-0.200 mm) for column chromatography (70-230 mesh ASTM)) eluted with n-pentane:EtOAc. The detailed experimental procedure, as well as the characterization of isolated compounds are provided in the Supporting Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With lithium acetate; palladium diacetate; triethylamine tris(hydrogen fluoride); tricyclohexylphosphine In 1,4-dioxane; water at 90℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(acetonitrile)copper(I)tetrafluoroborate; 1,4-diazabicyclo[2.2.2]octane-triethylenediamine-bis(sulfur dioxide); tetrabutyl ammonium fluoride; N,N`-dimethylethylenediamine In acetonitrile at 120℃; for 24h; Glovebox; Inert atmosphere; |
Tags: 780-69-8 synthesis path| 780-69-8 SDS| 780-69-8 COA| 780-69-8 purity| 780-69-8 application| 780-69-8 NMR| 780-69-8 COA| 780-69-8 structure
[ 17938-06-6 ]
Triethoxy(naphthalen-1-yl)silane
Similarity: 0.92
[ 123640-93-7 ]
4,4'-Bis(triethoxysilyl)-1,1'-biphenyl
Similarity: 0.84
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P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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