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CAS No. : | 18412-57-2 | MDL No. : | MFCD04974099 |
Formula : | C13H22O3Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PADYPAQRESYCQZ-UHFFFAOYSA-N |
M.W : | 254.40 | Pubchem ID : | 4670738 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
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 |
---|---|---|
81% | Stage #1: para-bromotoluene With n-butyllithium In hexane at 20℃; for 1h; Stage #2: tetraethoxy orthosilicate In hexane at -78℃; for 1h; Further stages.; | |
81% | Stage #1: para-bromotoluene With n-butyllithium In hexane at 20℃; Inert atmosphere; Stage #2: tetraethoxy orthosilicate In hexane at -78℃; for 1h; | |
72% | With magnesium In diethyl ether for 6h; Heating; |
58% | With iodine; magnesium In tetrahydrofuran for 12h; Inert atmosphere; Reflux; | |
(i) Mg, THF, Et2O, (ii) /BRN= 1422225/; Multistep reaction; | ||
Stage #1: para-bromotoluene With magnesium In tetrahydrofuran at 20℃; Stage #2: tetraethoxy orthosilicate In tetrahydrofuran at -30 - 20℃; for 13h; | ||
With Li In diethyl ether | ||
Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: tetraethoxy orthosilicate In tetrahydrofuran at -78 - 25℃; Inert atmosphere; | ||
With diethyl ether; lithium | ||
With lithium In diethyl ether | ||
Stage #1: para-bromotoluene With magnesium In tetrahydrofuran Reflux; Inert atmosphere; Stage #2: tetraethoxy orthosilicate In tetrahydrofuran at -30 - 20℃; for 13h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 1h; | |
80% | With N-ethyl-N,N-diisopropylamine; johnphos In 1-methyl-pyrrolidin-2-one at 60℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium hydroxide at 140℃; for 1.5h; | |
96% | With sodium hydroxide; tetrabutylammomium bromide at 120℃; for 3h; | |
91% | With sodium hydroxide In 1,4-dioxane at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 60℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 60℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With N-ethyl-N,N-diisopropylamine; johnphos In 1-methyl-pyrrolidin-2-one at 60℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium hydroxide; cyclo-octa-1,5-diene In 1,4-dioxane at 90℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With tris(dibenzylideneacetone)dipalladium (0); tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tris(dibenzylideneacetone)dipalladium (0); tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tris(dibenzylideneacetone)dipalladium (0); tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With tris(dibenzylideneacetone)dipalladium (0); tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With tris(dibenzylideneacetone)dipalladium (0); tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With tris(dibenzylideneacetone)dipalladium (0); tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium hydroxide In water at 90℃; for 3.5h; | |
82% | With tetrabutyl ammonium fluoride; acetic acid In toluene at 100℃; for 24h; | |
81% | With sodium hydroxide In water at 90℃; for 6h; |
80% | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; P(p-C6H4F)3 In water; toluene at 120℃; for 24h; Inert atmosphere; | |
77% | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; P(p-C6H4F)3 In toluene at 120℃; for 24h; Inert atmosphere; | |
73% | With tetrabutyl ammonium fluoride; 2,2'-bis(diisopropylphosphino)diphenyl ether In toluene at 80℃; for 18h; | |
37% | With sodium hydroxide In water at 120℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97 % Spectr. | With sodium hydroxide; tetrabutylammomium bromide at 120℃; for 0.25h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium hydroxide In water at 120℃; for 9h; | |
79% | With tetrabutyl ammonium fluoride; acetic acid In toluene at 100℃; for 24h; | |
72% | With sodium hydroxide at 120℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With N,N-bis(indolin-1-yl)ethane-1,2-diimine; tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 80℃; for 3h; | |
32% | With sodium hydroxide In water at 120℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With zinc(II) fluoride In 1,4-dioxane; water at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With silver fluoride; copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 110℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide In water at 90℃; for 3.5h; | |
38% | With tetrabutyl ammonium fluoride; acetic acid In toluene at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With sodium hydroxide In water at 120℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In 1,4-dioxane; water at 110℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With palladium diacetate; silver fluoride In 1,4-dioxane at 80℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium tosylate; triethylamine In N,N-dimethyl-formamide for 8h; Reflux; | |
85% | With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 0 - 80℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: 4-methylbenzenediazonium 4-methylbenzenesulfonate With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetra-(n-butyl)ammonium iodide; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: Triethoxysilane In N,N-dimethyl-formamide at 20 - 100℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With copper(II) sulfate supported on the solid alumina; potassium carbonate In tetrahydrofuran at 70℃; for 9h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With Pd((CH3)2C6H3NC(CH3)CHC(CH3)NC6H3(CH3)2)(CH3)(P(CH2CH3)3); tetrabutylammomium bromide; sodium hydroxide In water at 60℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With Pd((CH3)2C6H3NC(CH3)CHC(CH3)NC6H3(CH3)2)(CH3)(P(CH2CH3)3); tetrabutylammomium bromide; sodium hydroxide In water at 60℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With Pd((CH3)2C6H3NC(CH3)CHC(CH3)NC6H3(CH3)2)(CH3)(P(CH2CH3)3); tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 15h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | 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 |
---|---|---|
92% | With sodium hydroxide In water at 90℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79 %Spectr. | With Selectfluor; barium(II) oxide; silver(l) oxide In acetone at 23 - 90℃; for 2h; regioselective reaction; | 4.3.1. General procedure A (for volatile compounds) General procedure: To aryl silane (0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23 °C were added silver oxide (46.4 mg, 0.200 mmol, 2.00 equiv), barium oxide (15.6 mg, 0.100 mmol, 1.00 equiv), and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (1) (70.8 mg, 0.200 mmol, 2.00 equiv). The reaction mixture was stirred for 2 h at 90 °C in a sealed vial, then cooled to 23 °C. To the reaction mixture was added 3-nitrofluorobenzene (10.0 μL, 0.0939 mmol). The yields were determined by comparing the integration of the 19F NMR (375 MHz, acetone-d6, 23 °C) resonance of an aryl fluoride and that of 3-nitrofluorobenzene (-112.0 ppm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: N-benzyl-2,3-dihydro-2-phenyl-1H-pyridin-4-one With palladium diacetate In acetic acid; <i>tert</i>-butyl alcohol at 65℃; for 0.25h; Stage #2: p-tolyltriethoxysilane With copper (II)-fluoride In acetic acid; <i>tert</i>-butyl alcohol at 20 - 65℃; for 3.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With C14H16N6; palladium diacetate; silver fluoride In 1-methyl-pyrrolidin-2-one 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; P(p-C6H4F)3 In toluene at 120℃; for 12h; Inert atmosphere; | |
80% | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; P(p-C6H4F)3 In water; toluene at 120℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; water at 80℃; for 18h; | |
79% | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; P(p-C6H4F)3 In toluene at 120℃; for 12h; Inert atmosphere; | |
79% | With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; P(p-C6H4F)3 In water; toluene at 120℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; silver fluoride In 1,2-dichloro-ethane at 60℃; for 3h; Inert atmosphere; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; silver fluoride In 1,2-dichloro-ethane at 60℃; for 3h; Inert atmosphere; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | 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. |
40% | 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 |
---|---|---|
44% | 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 |
---|---|---|
58% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With palladium(II) trifluoroacetate; C30H30N4; silver fluoride; In N,N-dimethyl acetamide; at 110℃; 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 |
---|---|---|
79% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; silver fluoride In tetrahydrofuran; water at 80℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 48h; Sealed tube; | CuI-Catalyzed Couplings of Aryltriethoxysilanes with Aryl Iodidesand Bromides: General Procedure B (in the Absence of Ligand) General procedure: In a glovebox, aryl iodide (1.0 mmol), CsF (228 mg, 1.5 mmol), and CuI (19.0 mg, 0.1 mmol) were weighed into a 4-dram borosilicate scintillation vial and dissolved in DMF (5 mL). Aryltriethoxysilane (1.0 mmol) was then added to the mixture, and the vial was tightly capped with a poly-seal cone-lined urea cap (Wheaton). The mixture was taken out of the glovebox and placed in an oil bath preheated to 120 °C with vigorous stirring. After 48 h, the mixture was cooled to r.t., diluted with EtOAc (15 mL), and washed with H2O (2× 5 mL). The aqueous fraction was back-extracted with EtOAc (3 ×5 mL). The combined organic fractions were dried (Na2SO4) and cotton-filtered, and the solvent was removed on a rotary evaporator. The product was purified by column chromatography (silica gel, hexanes, hexanes-Et2O, or hexanes-EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 48h; Sealed tube; | CuI-Catalyzed Couplings of Aryltriethoxysilanes with Aryl Iodidesand Bromides: General Procedure B (in the Absence of Ligand) General procedure: In a glovebox, aryl iodide (1.0 mmol), CsF (228 mg, 1.5 mmol), and CuI (19.0 mg, 0.1 mmol) were weighed into a 4-dram borosilicate scintillation vial and dissolved in DMF (5 mL). Aryltriethoxysilane (1.0 mmol) was then added to the mixture, and the vial was tightly capped with a poly-seal cone-lined urea cap (Wheaton). The mixture was taken out of the glovebox and placed in an oil bath preheated to 120 °C with vigorous stirring. After 48 h, the mixture was cooled to r.t., diluted with EtOAc (15 mL), and washed with H2O (2× 5 mL). The aqueous fraction was back-extracted with EtOAc (3 ×5 mL). The combined organic fractions were dried (Na2SO4) and cotton-filtered, and the solvent was removed on a rotary evaporator. The product was purified by column chromatography (silica gel, hexanes, hexanes-Et2O, or hexanes-EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With copper(l) iodide; cesium fluoride; In N,N-dimethyl-formamide; at 120℃; for 48h;Sealed tube; | General procedure: In a glovebox, aryl iodide (1.0 mmol), CsF (228 mg, 1.5 mmol), and CuI (19.0 mg, 0.1 mmol) were weighed into a 4-dram borosilicate scintillation vial and dissolved in DMF (5 mL). Aryltriethoxysilane (1.0 mmol) was then added to the mixture, and the vial was tightly capped with a poly-seal cone-lined urea cap (Wheaton). The mixture was taken out of the glovebox and placed in an oil bath preheated to 120 C with vigorous stirring. After 48 h, the mixture was cooled to r.t., diluted with EtOAc (15 mL), and washed with H2O (2× 5 mL). The aqueous fraction was back-extracted with EtOAc (3 ×5 mL). The combined organic fractions were dried (Na2SO4) and cotton-filtered, and the solvent was removed on a rotary evaporator. The product was purified by column chromatography (silica gel, hexanes, hexanes-Et2O, or hexanes-EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 48h; Sealed tube; | CuI-Catalyzed Couplings of Aryltriethoxysilanes with Aryl Iodidesand Bromides: General Procedure B (in the Absence of Ligand) General procedure: In a glovebox, aryl iodide (1.0 mmol), CsF (228 mg, 1.5 mmol), and CuI (19.0 mg, 0.1 mmol) were weighed into a 4-dram borosilicate scintillation vial and dissolved in DMF (5 mL). Aryltriethoxysilane (1.0 mmol) was then added to the mixture, and the vial was tightly capped with a poly-seal cone-lined urea cap (Wheaton). The mixture was taken out of the glovebox and placed in an oil bath preheated to 120 °C with vigorous stirring. After 48 h, the mixture was cooled to r.t., diluted with EtOAc (15 mL), and washed with H2O (2× 5 mL). The aqueous fraction was back-extracted with EtOAc (3 ×5 mL). The combined organic fractions were dried (Na2SO4) and cotton-filtered, and the solvent was removed on a rotary evaporator. The product was purified by column chromatography (silica gel, hexanes, hexanes-Et2O, or hexanes-EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; C17H29N; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 48h; Sealed tube; | CuI-Catalyzed Couplings of Aryltriethoxysilanes with Aryl Iodidesand Bromides: General Procedure A (in the Presence of Ligand PN-1 or PN-2) General procedure: In a glovebox, aryl iodide (1.0 mmol), CsF (228 mg, 1.5 mmol), CuI (19.0 mg, 0.10 mmol), and PN-1 ligand (30 mg, 0.10 mmol) were weighed into a 4-dram borosilicate scintillation vial and dissolved in DMF (5 mL). Aryltriethoxysilane (1.0 mmol) was then added to the mixture, and the vial was tightly capped with a poly-seal conelined urea cap (Wheaton). The mixture was taken out of the glove box and placed in an oil bath pre-heated to 120 °C with vigorous stirring. After 48 h, the mixture was cooled to r.t., diluted with EtOAc (15 mL) and washed with H2O (3 × 5 mL). The aqueous fraction was back-extracted with EtOAc (3 × 5 mL). The combined organic fractions were dried (Na2SO4) and cotton-filtered, and the solvent was removed on a rotary evaporator. The product was purified by column chromatography (silica gel, hexanes, hexanes-Et2O, or hexanes-EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With copper(l) iodide; 2-benzhydryl-N,N-dimethylaniline; cesium fluoride; In N,N-dimethyl-formamide; at 120℃; for 48h;Sealed tube; | General procedure: In a glovebox, aryl iodide (1.0 mmol), CsF (228 mg, 1.5 mmol), CuI (19.0 mg, 0.10 mmol), and PN-1 ligand (30 mg, 0.10 mmol) were weighed into a 4-dram borosilicate scintillation vial and dissolved in DMF (5 mL). Aryltriethoxysilane (1.0 mmol) was then added to the mixture, and the vial was tightly capped with a poly-seal conelined urea cap (Wheaton). The mixture was taken out of the glove box and placed in an oil bath pre-heated to 120 C with vigorous stirring. After 48 h, the mixture was cooled to r.t., diluted with EtOAc (15 mL) and washed with H2O (3 × 5 mL). The aqueous fraction was back-extracted with EtOAc (3 × 5 mL). The combined organic fractions were dried (Na2SO4) and cotton-filtered, and the solvent was removed on a rotary evaporator. The product was purified by column chromatography (silica gel, hexanes, hexanes-Et2O, or hexanes-EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 1,4-diazabicyclo[2.2.2]octane-triethylenediamine-bis(sulfur dioxide); oxygen; copper diacetate; cesium fluoride; XPhos In 1,4-dioxane at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; water at 80℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; water at 80℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; water at 80℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; water at 80℃; for 18h; |
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; | 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 |
---|---|---|
99% | 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 |
---|---|---|
50% | With copper(II) fluoride dihydrate; {(1,3-bis(dimethylphosphino)propane)PdCl2}; bis-diphenylphosphinomethane In N,N-dimethyl acetamide at 100℃; Schlenk technique; |
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 |
---|---|---|
89% | 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 |
---|---|---|
87% | With palladium diacetate; silver fluoride; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 40℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With silver(II) fluoride; bis-diphenylphosphinomethane; bis(dibenzylideneacetone)-palladium(0) In toluene at 60℃; for 6h; | |
78% | With copper (II)-fluoride; bis(acetylacetonate)nickel(II); 1,10-Phenanthroline; cesium fluoride In dimethyl sulfoxide at 120℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With silver(II) fluoride; bis-diphenylphosphinomethane; bis(dibenzylideneacetone)-palladium(0) In toluene at 60℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With silver(II) fluoride; bis-diphenylphosphinomethane; bis(dibenzylideneacetone)-palladium(0) In toluene at 60℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: p-tolyltriethoxysilane With (1,2-dimethoxyethane)dichloronickel(II); cesium fluoride; 4,4'-di-tert-butyl-2,2'-bipyridine In 1,4-dioxane for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: ethyl bromofluoroacetate In 1,4-dioxane at 80℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.8% | With sodium hydroxide In ethanol; water for 0.166667h; Reflux; | 1.2.1 Synthesis of sodium cis-tritolylcyclotrisiloxanolate (method 1) Tolyltriethoxysilane (1.43 g, 5.6 mmol) were dissolved in 20 ml of ethanol containing (1 ml, 55.6 mmol) of H2O (H2O:Si = 10) and (0.252 g, 6.3 mmol) sodium hydroxide were charged in under stirring. The reaction mass got cloudy. Then the reaction mass was stirred under reflux for 10 min. Precipitation of white crystalline product was observed. After filtration and drying in vacuum (10 mm Hg) at 70oC 1.02g (88.8 %) of crystalline powder were obtained. Calcd: (%) for [CH3C6H4Si(O)O-]3(Na+)]3}*5H2O, C21H31Na3Si3O11. MM: 612. 73, C, 41.16; H, 5.10; Si, 13.75; Na, 11.26., Found: (%) C, 41.10; H, 5.16; Si, 13.42; Na, 11.42. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.8% | With sodium hydroxide In water Reflux; | 1.2.3 Synthesis of sodium cis-tetratolylcyclotetrasiloxanolate Tolyltriethoxysilane (4.74 g, 18.6 mmol), n-butanol (60 ml), sodium hydroxide (0.744 g, 18.6 mmol) and water (0.334 ml, 18.6 mmol) were stirred under reflux till the reaction mass became transparent and them 30 min more. The white crystals were precipitated from partially evaporated solution after its storage in a refrigerator in a few days. A suitable single crystal for X-ray analysis was taken from the mother liquor. The white crystals were filtered and dried on a rotor evaporator at 70oC/10 Hg mm. 4.8 g (78,8%) of white product were obtained Calcd: (%) for [CH3C6H4Si(O)O-]4(Na+)4]*74H9OH*5H2O, C56H110Na4Si4O21. MM: 1323.8, C, 50.80; H, 8.37; Si, 8.48; Na, 6.95. Found: (%) C, 50.39; H, 8.24; Si, 8.75; Na, 7.08. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With copper(ll) sulfate pentahydrate; 4,4'-Dimethoxy-2,2'-bipyridin; tetrabutyl ammonium fluoride; oxygen; toluene-4-sulfonic acid; phenol In tetrahydrofuran; methanol at 25℃; for 10h; | Preparation of 3a-3j To a tube were added RSSAc 2a-2q (0.2 mmol, 1 equiv.), CuSO4·5H2O (0.02 mmol, 10 mol%), 4,4’-diMeObipy (0.04 mmol, 20 mol%), TsOH·H2O (0.06 mmol, 0.3 equiv.), PhOH (0.1 mmol, 0.5 equiv.), aryltriethoxylsilane (0.6 mmol, 3 equiv.), TBAF solution 1.0 M in THF (0.1 mmol, 0.5 equiv.) and MeOH (2 mL), the mixture was stirred at 25°C for 10 h under O2 atmosphere before it was concentrated under vacuum. Purification by column chromatography afforded the desired product 3. 1-Benzyl-2-(p-tolyl)disulfane (3a) 73% yield, colorless oil; 1H NMR (400MHz, CDCl3) δ 7.39 (d, J=8.2Hz, 2H), 7.35-7.26 (m, 5H), 7.14 (d, J=8.0Hz, 2H), 3.97 (s, 2H), 2.37 (s, 3H); 13C NMR (100MHz, CDCl3) δ 137.1, 136.7, 133.6, 129.7, 129.4, 128.6, 128.5, 127.4, 43.3, 21.0; MS (EI) m/z 246 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With graphene immobilized iridium complex containing N-heterocyclic carbene ligand functionalized with pyrene at 30℃; for 0.583333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver fluoride; copper(II) sulfate In 1,4-dioxane at 80℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With 1,1'-bis-(diphenylphosphino)ferrocene; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 60℃; for 12h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With bis(triphenylphosphine)nickel(II) chloride; 1,10-Phenanthroline; cesium fluoride In 1,4-dioxane at 80℃; for 12h; Inert atmosphere; | 5 Weigh 2-bromo-2-fluoro-1-(thiophen-2-yl)ethane-1-one (0.134g, 0.6mmol), triethoxy(p-tolyl)silane (0.183g, 0.72mmol) , Bis (triphenylphosphine) nickel chloride (0.0392g, 0.0392mmol), 1,10-phenanthroline (0.0193g, 0.072mmol) and CsF (0.456g, 3.0mmol) dissolved in 2.5ml of 1, 4-dioxane was placed in a 250mL round-bottomed flask, and N2 was replaced three times. The reaction tube was placed in an oil bath and gradually heated to 80°C. The reaction was stirred for 12h and TLC monitored the reaction to be complete.After the reaction, the reaction solution was filtered, and the filtrate was extracted with ethyl acetate and water for 3-4 times to obtain an organic phase. The organic phases were combined and concentrated, using petroleum ether: ethyl acetate = 20:1 as the eluent for column chromatography Separate, and finally obtain a white solid (yield 71%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With bis(triphenylphosphine)nickel(II) chloride; 1,10-Phenanthroline; cesium fluoride In 1,4-dioxane at 80℃; for 12h; Inert atmosphere; | 6 Weigh 2-bromo-2-fluoro-1-(p-tolyl)ethane-1-one (0.139g, 0.6mmol), triethoxy(p-tolyl)silane (0.183g, 0.72mmol), double (Triphenylphosphine) nickel chloride (0.0392g, 0.0392mmol), 1,10-phenanthroline (0.0193g, 0.072mmol) and CsF (0.456g, 3.0mmol) dissolved in 2.5ml of 1,4- Dioxane was placed in a 250mL round-bottomed flask and replaced with N2 three times. The reaction tube was placed in an oil bath and gradually heated to 80°C. The reaction was stirred for 12h and TLC monitored the reaction to be complete.After the reaction, the reaction solution was filtered, and the filtrate was extracted with ethyl acetate and water for 3-4 times to obtain an organic phase. The organic phases were combined and concentrated, using petroleum ether: ethyl acetate = 20:1 as the eluent for column chromatography After separation, a colorless oil was finally obtained (yield 75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | 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 |
---|---|---|
88% | 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 |
---|---|---|
93% | 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 |
---|---|---|
50% | With 2-((2,4,6-trimethylphenyl)amino)-4-((2,4,6-trimethylphenyl)imino)-2-pentene; cobalt(II) aceylacetonate; magnesium In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With 1,10-Phenanthroline; oxygen; palladium diacetate In water at 80℃; for 9h; Schlenk technique; Sealed tube; | 3.2. General procedures for the synthesis of 3-arylquinoxalin-2(1H)-ones. General procedure: A dried 25 mL Schlenk tube equipped with a magnetic stir bar was charged with 1a (0.2 mmol, 1.0 equiv), 2a (0.4 mmol, 2.0 equiv), Pd(OAc)2 (10 mol%), 1,10-Phen (10 mol%), H2O (6 mL). Subsequently, the tube was sealed and the resulting mixture was stirred under oxygen at 80 °C for 9 h. The reaction progress was monitored by TLC. The reaction mixture was concentrated in vacuo, then extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography to produce the desired product (purified by flash chromatography (PE:EA = 4:1)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.4% | With silver fluoride In butanone at 60℃; for 12h; | 8 Example 8. Preparation of diethyl 1-(p-tolyl)hydrazine-1,2-dicarboxylate: Add 0.3mmol of AgF, 0.2mmol of p-methylphenyltriethoxysilane, 0.3mmol of diethyl azodicarboxylate, 2mL of methyl ethyl ketone solution and a magnet No. 5 in order, and turn the condenser through from bottom to top. After the water was condensed, the reactor was placed in an oil bath at 60°C and heated for 12 hours to react. The spherical container at the bottom of the reactor is immersed in silicone oil, and the immersion depth is such that the height of the silicone oil is higher than the height of the reaction solution in the spherical container of the micro reaction tube. The rotation speed of the magnetic stirrer was adjusted to 700 revolutions/s. After the reaction, the reaction solution was poured into a separatory funnel, 15 mL of distilled water was added, and the mixture was extracted 3 times with 10 mL of ethyl acetate. The obtained organic phases are combined and spin-dried on a rotary evaporator. The crude product is separated and purified by column chromatography to obtain 34.33 mg of 1-(4-methylphenyl)hydrazine-1,2-dicarboxylate diethyl ester, which is a pale yellow oily liquid. Drops, the yield was 64.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With silver(I) fluoride In butanone at 60℃; for 12h; Inert atmosphere; |
Tags: 18412-57-2 synthesis path| 18412-57-2 SDS| 18412-57-2 COA| 18412-57-2 purity| 18412-57-2 application| 18412-57-2 NMR| 18412-57-2 COA| 18412-57-2 structure
[ 123640-93-7 ]
4,4'-Bis(triethoxysilyl)-1,1'-biphenyl
Similarity: 0.93
[ 17938-06-6 ]
Triethoxy(naphthalen-1-yl)silane
Similarity: 0.84
[ 18001-13-3 ]
Trimethoxy(4-vinylphenyl)silane
Similarity: 0.82
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