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[ CAS No. 789-25-3 ] {[proInfo.proName]}

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Chemical Structure| 789-25-3
Chemical Structure| 789-25-3
Structure of 789-25-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 789-25-3 ]

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Product Details of [ 789-25-3 ]

CAS No. :789-25-3 MDL No. :MFCD00003003
Formula : C18H16Si Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :260.41 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 789-25-3 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 85.38
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.12
Log Po/w (XLOGP3) : 5.32
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 5.16
Log Po/w (SILICOS-IT) : 3.61
Consensus Log Po/w : 3.83

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.31
Solubility : 0.00128 mg/ml ; 0.00000491 mol/l
Class : Moderately soluble
Log S (Ali) : -5.07
Solubility : 0.00221 mg/ml ; 0.00000848 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.54
Solubility : 0.00000754 mg/ml ; 0.000000029 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.34

Safety of [ 789-25-3 ]

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

Application In Synthesis of [ 789-25-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 789-25-3 ]

[ 789-25-3 ] Synthesis Path-Downstream   1~81

  • 1
  • [ 591-51-5 ]
  • [ 789-25-3 ]
  • [ 1048-08-4 ]
YieldReaction ConditionsOperation in experiment
90% In not given byproducts: LiH;
90% In not given byproducts: LiH;
With diethyl ether
  • 2
  • [ 100-51-6 ]
  • [ 789-25-3 ]
  • [ 18858-69-0 ]
YieldReaction ConditionsOperation in experiment
57% With potassium hexamethylsilazane; In neat liquid; at 30℃; for 4.0h;Schlenk technique; Inert atmosphere; General procedure: Catalyzed CDC reactions were carried out using the following standard protocol. In the glove box, the chosen pre-catalyst (0.05 mmol) was loaded into a Schlenk tube, and subsequently the alcohol (n x 0.05 mmol, n equiv.) followed by silane (n' x 0 0.05 mmol, n' equiv.) were added. The reaction mixture was stirred at the desired temperature (30C), which was controlled by an oil bath. After the required period, the reaction was quenched by adding CDCl3 to the mixture. Substrate conversion was monitored by examination of the 1H NMR spectrum of the reaction mixture and comparing relative intensities of resonance characteristics of the substrates and products.
  • 3
  • [ 108-95-2 ]
  • [ 789-25-3 ]
  • [ 1169-05-7 ]
YieldReaction ConditionsOperation in experiment
86% With tert.-butylhydroperoxide; ammonium iodide; In water; at 80℃; for 24.0h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%).
83% With indium(III) bromide; In toluene; for 1.0h;Inert atmosphere; Reflux; Typical procedure for O-silylation with a hydrosilane using InBr3 as a catalyst: (-)-Menthol (1.0 g, 6.4 mmol), triethylsilane (0.7 g, 6.4 mmol) and toluene (10 ml) were taken into a 50 ml two neck round-bottomed flask fitted with a condenser, rubber septa and an argon balloon. InBr3 (0.1 g, 0.32 mmol) was added to the contents in the flask under purge of argon and the mixture was refluxed for 2 h under argon atmosphere. Progress of the reaction was by TLC and after completion of the reaction, the reaction mixture was cooled to room temperature and solvent was removed under reduced pressure. The crude product was extracted with ethyl acetate (2 × 5 ml) and the combined organic layer was washed with water (1 × 3 ml) and saturated NaCl solution (1 × 3 ml) and dried over anhyd. Na2SO4. Next, the solvent was removed under reduced pressure and the crude product was purified by normal column chromatography (Silica gel (60-120 mesh, hexane) to obtain (menthyloxy)triethylsilane (01.36 g, 80%) in the form of a colourless oil and it was characterized by the following spectral data:
  • 6
  • [ 789-25-3 ]
  • [ 1450-23-3 ]
  • [ 791-29-7 ]
YieldReaction ConditionsOperation in experiment
With sodium-potassium alloy und anschliessend mit CH3I;
  • 7
  • [ 789-25-3 ]
  • [ 791-31-1 ]
YieldReaction ConditionsOperation in experiment
>99% With oxygen; In water; acetone; at 30℃; under 760.051 Torr; for 0.5h; General procedure: A typical reaction procedure for the oxidation of 1 to 2 using Au/HAP was as follows.Au/HAP (0.005 g, Au: 0.0415 mol%) was placed in a reaction vessel (50 cm3), followedby the addition of acetone (4 mL), water (0.1 mL), and 1 (1 mmol). The reactionmixture was vigorously stirred at 30 C under O2 atmosphere for 7 min. Au/HAP wasfiltered and the yield was determined by GC analysis. The product was isolated byKugelrohr distillation.
99% With water; copper(II) oxide; In ethyl acetate; at 80℃; for 12.0h; 3 mmol) was mixed with water (lOmmol), 4 mL of ethyl acetate was added, copper oxide was used as a catalyst,The catalyst was used in an amount of 1% of the moles of <strong>[789-25-3]triphenylsilane</strong>, reacted in air, heated to 80 C with stirring, and the reaction time was 12 hours. After completion of the reaction, the mixture was concentrated and washed with water to obtain white crystals of triphenylsilanol 8b. The conversion of the starting material was 100% and the yield of triphenylsilanol 8b was 99%.
99% With water; oxygen; In tetrahydrofuran; at 20℃; for 12.0h;Irradiation;Catalytic behavior; General procedure: To a solution of Rose Bengal (0.008 mmol, 2 mol%) in THF2 mL was added silane 1 (0.4 mmol, 1 equiv.) and H2O (50muL). The reaction mixture was open to the air (with a syringeneedle inserted into the rubber cover to intoduce the air intothe system and avoid the solvent evaporation heavily, thesame below), and stirred under the irradiation of a household200 W white LED at room temperature for 12 h. Aftercompletion of the reaction (monitored by GC-MS or TLC),the solvent was removed under reduced pressure, the crudeproduct was purified by column chromatography with petroleumether/ethyl acetate (10:1) as eluent to give the desiredsilanol 2.
95% With silver; water; In acetone; at 20℃; for 6.0h; General procedure: The preparation of dimethylphenylsilanol 2a was given as a representative example. Nanoporous silver (10 mg), acetone (1.5 mL), H2O(0.1 mL), and dimethylphenylsilane 1a (1 mmol) were added in a micro-reaction vial at room temperature. The mixture was stirred for 60 min until no bubbles emerged, and then the np-Ag was removed from the system. The reaction mixture was then concentrated by rotary evaporation and the residue was purified by column chromatography on silica gel using ethyl acetate/petroleum ether (60-90 C) (1:1) as eluent to give 2a. The recovered catalyst was washed with acetone and water and was reused without further purification.
88% With water; In dimethyl sulfoxide; at 120℃;Inert atmosphere; Glovebox; In a 15 ml reaction tube equipped with a magnetic stir bar, sent to a glove box, adding 156.0 mg of <strong>[789-25-3]triphenylsilane</strong>, 2 ml of dimethyl sulfoxide, 324 ul of water, under an argon atmosphere, The temperature is 120 C, the magnetic stirrer is carried out at 800 rpm, and the reaction progress is detected by TLC. After the silane reaction is completed, the target product is extracted and concentrated to obtain triphenylsilanol, a white solid, melting point of 152-153 C. The yield is 88% (based on silane),

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[5]Journal of Organic Chemistry,2016,vol. 81,p. 4190 - 4195
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[11]Organometallics,2020,vol. 39,p. 165 - 171
[12]Inorganic Chemistry,2010,vol. 49,p. 383 - 385
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    Angew. Chem.,2019,vol. 131,p. 6446 - 6450,5
[14]Catalysis Communications,2014,vol. 53,p. 53 - 56
[15]Catalysis science and technology,2015,vol. 5,p. 4542 - 4546
[16]Chemical Communications,2016,vol. 52,p. 10625 - 10628
[17]Journal of Organometallic Chemistry,1996,vol. 521,p. 229 - 234
[18]Zeitschrift fur Naturforschung, B: Chemical Sciences,1991,vol. 46,p. 783 - 788
[19]Journal of Organometallic Chemistry,1996,vol. 521,p. 229 - 234
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[23]Chemistry - A European Journal,2011,vol. 17,p. 9897 - 9900
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[26]Journal of the Chemical Society,1929,p. 361,364,365
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[28]Tetrahedron Letters,1994,vol. 35,p. 6329 - 6330
[29]Journal of Chemical Research - Part S,1997,p. 400 - 401
[30]Synlett,2002,p. 1173 - 1175
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[32]European Journal of Inorganic Chemistry,2010,p. 5675 - 5684
[33]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Si: MVol.C, 23, page 72 - 75
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  • 8
  • [ 108-93-0 ]
  • [ 789-25-3 ]
  • [ 20466-67-5 ]
YieldReaction ConditionsOperation in experiment
72% With tert.-butylhydroperoxide; ammonium iodide; In water; at 20℃; for 24.0h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%).
  • 9
  • [ 18666-68-7 ]
  • [ 789-25-3 ]
  • [ 18822-04-3 ]
YieldReaction ConditionsOperation in experiment
In ethanol; Petroleum ether Heating;
  • 10
  • [ 71-36-3 ]
  • [ 789-25-3 ]
  • [ 1829-44-3 ]
YieldReaction ConditionsOperation in experiment
89% With tert.-butylhydroperoxide; ammonium iodide; In water; at 20℃; for 24.0h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%).
  • 11
  • [ 64-17-5 ]
  • [ 789-25-3 ]
  • [ 1516-80-9 ]
YieldReaction ConditionsOperation in experiment
94% With potassium hexamethylsilazane; In neat liquid; at 60℃; for 2.0h;Schlenk technique; Inert atmosphere; General procedure: Catalyzed CDC reactions were carried out using the following standard protocol. In the glove box, the chosen pre-catalyst (0.05 mmol) was loaded into a Schlenk tube, and subsequently the alcohol (n x 0.05 mmol, n equiv.) followed by silane (n' x 0 0.05 mmol, n' equiv.) were added. The reaction mixture was stirred at the desired temperature (30C), which was controlled by an oil bath. After the required period, the reaction was quenched by adding CDCl3 to the mixture. Substrate conversion was monitored by examination of the 1H NMR spectrum of the reaction mixture and comparing relative intensities of resonance characteristics of the substrates and products.
92% With tert.-butylhydroperoxide; ammonium iodide; In water; at 20℃; for 24.0h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%). 1H NMR (300 MHz, CDCl3): delta = 7.66 (d, J = 6.4 Hz, 6 H), 7.42 (dt, J = 13.5, 6.6 Hz, 9 H), 3.90 (q,J = 7.0 Hz, 2 H), 1.26 (t, J = 6.9 Hz, 3 H). 13C NMR (75 MHz,CDCl3): delta = 135.49, 134.55, 130.06, 127.95, 59.85, 18.49. HRMS(TOF, EI+): m/z calcd for C20H20OSi: 304.1283; found: 304.1285.
With dodecacarbonyl-triangulo-triruthenium; at 80℃; for 7.0h; General procedure: In a typical reaction, Et3SiH (1.56 mmol) and the various substrates (1.56 mmol) were added to a benzene or toluene solution containing Ru3(CO)12 (0.01 g, 0.0156 mmol). The mixture was heated in vacuo at 80 C for 4 h. For optimization studies, various conditions as shown in Table 1 have been used. After reaction, NMR was taken with CDCl3 as the solvent [34]. For isolated yield determination, the catalytic mixture containing selected products as described in Table 2 was concentrated and passed through a column of silica gel 60 of dimension Ø14 × 180 mm using a 1:1 mixture of hexane and chloroform.
  • 12
  • [ 108-97-4 ]
  • [ 789-25-3 ]
  • [ 77249-51-5 ]
  • 13
  • [ 694-53-1 ]
  • [ 1048-08-4 ]
  • [ 775-12-2 ]
  • [ 789-25-3 ]
YieldReaction ConditionsOperation in experiment
1: 5% 2: 5% 3: 24% With potassium hydride In 1,2-dimethoxyethane for 14h; Ambient temperature;
1: 4.8 % Chromat. 2: 26.6 % Chromat. 3: 0.2 % Chromat. In tetrahydrofuran at 50℃; for 6h;
With Na; K In decalin heating of (C6H5)SiH3 with Na in presence of some K in boiling decalin;;
  • 14
  • [ 775-12-2 ]
  • [ 1048-08-4 ]
  • [ 789-25-3 ]
YieldReaction ConditionsOperation in experiment
1: 35% 2: 12% With potassium hydride In 1,2-dimethoxyethane for 24h; Ambient temperature;
With potassium Sodium In diethyl ether (C6H5)2SiH2 and Na-K-alloy in ether at room temp.;;
With Na-K In diethyl ether (C6H5)2SiH2 and Na-K-alloy in ether at room temp.;;
With Na In decalin (C6H5)2SiH2 and Na in boiling decalin;;

  • 15
  • [ 1516-80-9 ]
  • [ 789-25-3 ]
YieldReaction ConditionsOperation in experiment
69% With diisobutylaluminium hydride In toluene at -78℃; for 0.5h;
With diisobutylaluminium hydride In toluene at 50 - 60℃; for 48h; Inert atmosphere;
  • 17
  • [ 754-05-2 ]
  • [ 789-25-3 ]
  • [ 6231-76-1 ]
  • [ 768-32-1 ]
  • [ 766-77-8 ]
  • [ 791-29-7 ]
  • C23H28Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 91.8% 2: 1.3% 3: 0.9% 4: 0.5% 5: 0.2% With dihydrogen hexachloroplatinate Heating; determination of side products;
  • 18
  • [ 108-05-4 ]
  • [ 789-25-3 ]
  • [ 1516-80-9 ]
  • [ 18666-87-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate 1.) toluene, RT, 63 h, 2.) MeOH, RT, 1 h; Multistep reaction. Yields of byproduct given;
With potassium carbonate 1.) toluene, RT, 63 h, 2.) MeOH, RT, 1 h; Yield given. Multistep reaction;
  • 19
  • [ 112-66-3 ]
  • [ 789-25-3 ]
  • [ 112-40-3 ]
  • [ 1929-33-5 ]
YieldReaction ConditionsOperation in experiment
67% With di-tert-butyl peroxide at 140℃; for 12h;
  • 20
  • [ 151-05-3 ]
  • [ 789-25-3 ]
  • [ 538-93-2 ]
  • [ 1929-33-5 ]
YieldReaction ConditionsOperation in experiment
43% With di-tert-butyl peroxide at 140℃; for 12h;
  • 21
  • [ 6221-92-7 ]
  • [ 789-25-3 ]
  • [ 294-62-2 ]
  • [ 1929-33-5 ]
  • 22
  • phenylmagnesium chloride [ No CAS ]
  • [ 789-25-3 ]
  • [ 1048-08-4 ]
YieldReaction ConditionsOperation in experiment
12.6% In tetrahydrofuran at 50℃; for 2h;
  • 23
  • [ 104023-26-9 ]
  • [ 789-25-3 ]
  • [ 294-62-2 ]
  • C22H22O2Si [ No CAS ]
  • 24
  • [ 104023-27-0 ]
  • [ 789-25-3 ]
  • [ 294-62-2 ]
  • C23H24O2Si [ No CAS ]
  • 25
  • [ 76733-12-5 ]
  • [ 789-25-3 ]
  • [ 294-62-2 ]
  • C24H26O2Si [ No CAS ]
  • 26
  • [ 70443-66-2 ]
  • [ 789-25-3 ]
  • [ 294-62-2 ]
  • [ 20428-56-2 ]
  • 27
  • [ 51354-26-8 ]
  • [ 789-25-3 ]
  • [ 629-59-4 ]
  • [ 1929-33-5 ]
YieldReaction ConditionsOperation in experiment
88% With di-tert-butyl peroxide at 140℃; for 12h;
  • 28
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
YieldReaction ConditionsOperation in experiment
99% With ethanol; iodine; potassium hydroxide at 20℃; for 24h;
98% With water; 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In acetonitrile at 20℃; for 2h; Schlenk technique; Glovebox;
97% With cesium fluoride In N,N-dimethyl-formamide for 14h; Ambient temperature;
95% With indium(III) bromide; oxygen In tetrahydrofuran at 20℃; for 5h;
91% With sodium hydroxide; ethanol at 100℃; for 4h;
89% With C15H27Br2CoN3; potassium <i>tert</i>-butylate; water In 1,4-dioxane at 60℃; for 2h;
69% With bis(1,5-cyclooctadiene)nickel(0); 3,4,7,8-Tetramethyl-o-phenanthrolin In toluene at 90℃; for 5h; Schlenk technique; Typical procedure for the synthesis to Disiloxanes General procedure: Ni(COD)2 (5.5 mg, 0.02 mmol), 3,4,7,8 -Tetramethyl-1,10-phenanthroline (5.7 mg, 0.024 mmol), 1.0 mL toluene were added to a Schlenk tube under argon atmosphere. The resulting solution was stirred at added to a Schlenk tube under argon atmosphere. The resulting solution was stirred at room temperature for 30 min, then the organosilane 1a (54.5 mg, 0.4 mmol) was added and the mixture was stirred at 70 °C under atmosphere with GC monitoring until the complete consumption of 1a. The residue was purified by silica gel column chromatography to afford the corresponding disiloxane 2a (55.6 mg, 97% yield).
50% With N,N-dimethyl-formamide; molybdenum hexacarbonyl at 120℃; for 48h; Heating;
With water In acetonitrile at 25℃; ΔH(excit.); variation of concentration;
With tetra(n-butyl)ammonium hydroxide In acetonitrile at 25℃;
With oxygen In benzene at 60℃; for 144h;
With KOH In potassium hydroxide aq. KOH; heating of (C6H5)3SiH with 30% aq. KOH;;
With KOH In potassium hydroxide aq. KOH; decompn. of (C6H5)3SiH with 30% aq. KOH at elevated temp.;;

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[11]Egger, Christian; Schubert, Ulrich [Zeitschrift fur Naturforschung, B: Chemical Sciences, 1991, vol. 46, # 6, p. 783 - 788]
[12]Khaskin, I. G. [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 32 - 37][C. A., 1954, p. 563] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 36, page 111 - 115]
[13]Khaskin, I. G. [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 32 - 37][C. A., 1954, p. 563] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 94, page 257 - 259]
[14]Hayashi, K.; Iyoda, J.; Shiihara, I. [Journal of Organometallic Chemistry, 1967, vol. 10, p. 81 - 94]
  • 29
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
  • [ 379-50-0 ]
  • 31
  • [ 16356-02-8 ]
  • [ 789-25-3 ]
  • (E)-1,4-dimethoxy-1-triphenylsilyl-2-buten [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In tetrahydrofuran for 24h; Ambient temperature;
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 100℃; for 6h; Green chemistry; (a) Procedure for hydrosilylation of alkynes performed in toluene or THF General procedure: A silane and an appropriate alkyne were placed in a 25cm3 round bottom flask equipped with a stirrer and a glass stopper. The reagents were dissolved in toluene or THF and Karstedt’s catalyst was added. Subsequently, the reaction mixture was heated to 60°C or 100°C, depending on the reaction. Samples of the reaction mixture were collected in intervals, and the conversion of SiH was determined by 1H NMR and GC-MS. Then the reactions were repeated in determined reaction time, and the resulting mixtures were isolated by the evaporation of the solvent under vacuum. Products were characterized by 1H, 13C, 29Si NMR, GC-MS analysis. The platinum residue was removed by filtration of petroleum ether solution through silica gel. After evaporation of solvents, the products were dried for 6h under vacuum. Isolated products were characterized by 1H, 13C, 29Si NMR, GC-MS. For new compounds, elemental analysis was performed as well.
  • 32
  • [ 3317-61-1 ]
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
  • 2,2-Dimethyl-1-triphenylsilanyloxy-pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 11% 2: 65% In benzene at 80℃; for 15h;
  • 33
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
  • 2,2-Dimethyl-1-triphenylsilanyloxy-pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 65% 2: 11% With 5,5-Dimethyl-1-pyrroline N-oxide In benzene at 80℃; for 15h;
  • 34
  • [ 67-63-0 ]
  • [ 789-25-3 ]
  • [ 1829-43-2 ]
YieldReaction ConditionsOperation in experiment
75% With tert.-butylhydroperoxide; ammonium iodide; In water; at 20℃; for 24.0h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%).
  • 35
  • [ 67-56-1 ]
  • [ 789-25-3 ]
  • [ 1829-41-0 ]
YieldReaction ConditionsOperation in experiment
99% With potassium hexamethylsilazane; In neat liquid; at 30℃; for 2.0h;Schlenk technique; Inert atmosphere; General procedure: Catalyzed CDC reactions were carried out using the following standard protocol. In the glove box, the chosen pre-catalyst (0.05 mmol) was loaded into a Schlenk tube, and subsequently the alcohol (n x 0.05 mmol, n equiv.) followed by silane (n' x 0 0.05 mmol, n' equiv.) were added. The reaction mixture was stirred at the desired temperature (30C), which was controlled by an oil bath. After the required period, the reaction was quenched by adding CDCl3 to the mixture. Substrate conversion was monitored by examination of the 1H NMR spectrum of the reaction mixture and comparing relative intensities of resonance characteristics of the substrates and products.
85% With tert.-butylhydroperoxide; ammonium iodide; In water; at 20℃; for 24.0h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%).
  • 36
  • [ 115-19-5 ]
  • [ 789-25-3 ]
  • (E)-2-methyl-4-(triphenylsilyl)but-3-en-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With gold nanoparticles on TiO2; In 1,2-dichloro-ethane; at 70℃; for 6.0h; General procedure: To a vial containing phenylacetylene, 6 (67 muL, 0.6 mmol), dimethylphenylsilane (0.155 mL, 1.0 mmol), and 1,2-dichloroethane (2 mL) were added Au/TiO2 (95 mg, 1 wt % in Au, ?0.005 mmol). The reaction was heated to 70 C for 2 h, and then the slurry was filtered with the aid of dichloromethane (3 mL) through a short pad of silica gel. The filtrate was evaporated under vacuum and the residue was chromatographed with hexane as eluent to afford a mixture containing 6c and 6d (135 mg, 86% yield) in a relative ratio of 88/12.
  • 37
  • [ 79-50-5 ]
  • [ 789-25-3 ]
  • 4,4-dimethyl-3-triphenylsilanyloxy-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tris(pentafluorophenyl)borate In dichloromethane for 2h; Ambient temperature;
  • 38
  • [ 10008-73-8 ]
  • [ 28868-76-0 ]
  • [ 789-25-3 ]
  • [ 53295-30-0 ]
  • 5-triphenylsilylmethyltetrahydrofuran-2-one [ No CAS ]
  • 39
  • [ 60-12-8 ]
  • [ 789-25-3 ]
  • [ 18758-56-0 ]
YieldReaction ConditionsOperation in experiment
85% With tert.-butylhydroperoxide; ammonium iodide; In water; at 20℃; for 24.0h; General procedure: 70% aq TBHP (4.0 mmol) was added dropwise over 10 min to asolution of the appropriate silane (1.0 mmol) and NH4I (0.20mmol) in the appropriate alcohol (1 mL), and the mixture wasstirred at r.t. until the reaction was complete (TLC). The reactionwas then quenched with sat. aq Na2S2O3, and the mixture waswashed with brine, extracted with EtOAc, dried (Na2SO4), andconcentrated under vacuum. The crude product was purified bycolumn chromatography (silica gel, PE).Ethoxy(triphenyl)silane (3aa)Colorless liquid; yield: 280 mg (92%).
  • 40
  • [ 64-17-5 ]
  • [ 789-25-3 ]
  • [ 1516-80-9 ]
YieldReaction ConditionsOperation in experiment
With piperidine at 33℃;
  • 41
  • [ 110-38-3 ]
  • [ 789-25-3 ]
  • [ 112-31-2 ]
  • 42
  • [ 67-63-0 ]
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
  • [ 1829-43-2 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; 18-crown-6 ether In dichloromethane-d2 at 20℃; for 18h; Title compound not separated from byproducts.;
  • 43
  • [ 2009-83-8 ]
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
  • (6-chloro-hexyloxy)-triphenyl-silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; 18-crown-6 ether In dichloromethane at 20℃; for 18h; Title compound not separated from byproducts.;
  • 44
  • [ 589-18-4 ]
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
  • ((4-methylbenzyl)oxy)triphenylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; 18-crown-6 ether In dichloromethane at 20℃; for 18h; Title compound not separated from byproducts.;
  • 45
  • [ 1123-85-9 ]
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
  • triphenyl-(2-phenyl-propoxy)-silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; 18-crown-6 ether In dichloromethane at 20℃; for 18h; Title compound not separated from byproducts.;
  • 46
  • [ 789-25-3 ]
  • [ 1048-08-4 ]
YieldReaction ConditionsOperation in experiment
1.0 % Chromat. With sodium ethanolate In 1,2-dimethoxyethane at 50℃; for 6h;
Multi-step reaction with 3 steps 1: not given 2: Cl2 / not given 3: not given
Multi-step reaction with 3 steps 1: Na-K / diethyl ether 2: diethyl ether 3: Na-K; C6H5I / diethyl ether
  • 47
  • [ 498-07-7 ]
  • [ 789-25-3 ]
  • 2,4-O-bis(triphenylsilyl)-1,6-anhydro-D-glucose [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With Proton Sponge; N,N-dimethyl acetamide at 60℃;
  • 48
  • [ 101268-55-7 ]
  • [ 789-25-3 ]
  • 4,4-bis(carbethoxy)-1-(Z)-triphenylsilylmethylidene-2-methylcyclopentane [ No CAS ]
  • 49
  • [ 536-74-3 ]
  • [ 789-25-3 ]
  • [ 33105-35-0 ]
YieldReaction ConditionsOperation in experiment
80% With C24H23ClCrIrNO3; In 1,1,2,2-tetrachloroethane; at 40℃; for 2.0h;Inert atmosphere; Schlenk technique; General procedure: Under nitrogen, alkyne reagent (0.15 mmol, 1 eq.) and selectediridium(III) catalyst (×mol%) were introduced in a Schlenk tubealong with internal reference 1,3,5-trimethoxybenzene (1 eq.). TCEsolvent (2 mL) was added followed by silane reagent (0.18 mmol,1.2 eq.). The reaction mixture was then heated at the selectedtemperature under stirring. In order to follow the progress of thereaction, aliquots (0.1 mL) were taken at defined times, filteredthrough Celite with a CH2Cl2wash (3 mL), evaporated under vac-uum and analysed by1H NMR.
  • 50
  • [ 698-70-4 ]
  • [ 789-25-3 ]
  • [ 18840-19-2 ]
  • [ 121-69-7 ]
  • 51
  • [ 15508-76-6 ]
  • [ 789-25-3 ]
  • [ 1520-44-1 ]
  • 52
  • [ 18282-40-1 ]
  • [ 789-25-3 ]
  • (2-ethylphenyl)triphenylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With potassium phosphate In 1-methyl-pyrrolidin-2-one at 20℃; for 168h;
93% With potassium phosphate In 1-methyl-pyrrolidin-2-one at 20℃; for 168h;
  • 53
  • [ 124-38-9 ]
  • [ 789-25-3 ]
  • CH2(OSiPh3)2 [ No CAS ]
  • [ 1829-40-9 ]
YieldReaction ConditionsOperation in experiment
1: 64% 2: 28% With [(1,3-bis(3-tBu-5-Me-2-oxy-benzyl)-4-Me-MeOC6H2]Zr(CH2Ph)2; tris(pentafluorophenyl)borate In toluene at 20℃; for 384h;
  • 54
  • [ 789-25-3 ]
  • [ 76-86-8 ]
  • [ 791-31-1 ]
YieldReaction ConditionsOperation in experiment
1: 93% 2: 6% With chlorine dioxyde In acetonitrile at 25℃; for 200h; Inert atmosphere; Oxidation of silanes 1-9 with chlorine dioxide. General procedure: The ClO 2 solution was kept in an argon atmosphere at 25°C for 5 min before adding the silane. The required amount of silane was added to a solution of chlorine dioxide (0.01- 0.6 M) in acetonitrile at room temperature. The reaction path was monitored using GLC or gas chromatography-mass spectrometry. After the reaction completion, the solvent was removed, the products were separated by preparative gas chromatography or on a column, the eluent was hexane-diethyl ether.
1: 93% 2: 6% With chlorine dioxyde In acetonitrile at 25℃; for 200h; Inert atmosphere; Oxidation of silanes 1-9 with chlorine dioxide. General procedure: The ClO 2 solution was kept in an argon atmosphere at 25°C for 5 min before adding the silane. The required amount of silane was added to a solution of chlorine dioxide (0.01- 0.6 M) in acetonitrile at room temperature. The reaction path was monitored using GLC or gas chromatography-mass spectrometry. After the reaction completion, the solvent was removed, the products were separated by preparative gas chromatography or on a column, the eluent was hexane-diethyl ether.
With tert.-butylhydroperoxide; tetrachloromethane; aluminum tri-tert-butoxide at 20℃; for 5h;
  • 55
  • C27H45P3SiRh [ No CAS ]
  • [ 2875-18-5 ]
  • C14H30P3RhF4N [ No CAS ]
  • C14H31P3RhF3N [ No CAS ]
  • [ 379-50-0 ]
  • [ 789-25-3 ]
  • 56
  • [ 789-25-3 ]
  • [ 33729-92-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 68 percent / toluene / 0.25 h / 0 °C 2: pentane / 1.) -50 deg C, 30 min, 2.) to r.t.
  • 57
  • [ 105669-94-1 ]
  • [ 789-25-3 ]
  • [ 64666-54-2 ]
  • [ 791-29-7 ]
  • [ 1829-41-0 ]
YieldReaction ConditionsOperation in experiment
1: 88% 2: 88% 3: 0% In dichloromethane (η5-C5Me5)Fe(CO)2(CHOMe))PF6 and Ph3SiH (Ar, CH2Cl2, -60°C), stirring for 2 h, warming to room temp.; removal of solvent (vac.), extn. (ether), chromy. (silca plates, petroleum ether); GC (180°C), 1H-NMR, MS;
  • 58
  • [ 98-13-5 ]
  • [ 1048-08-4 ]
  • [ 789-25-3 ]
YieldReaction ConditionsOperation in experiment
With sodium In further solvent(s) heating of (C6H5)SiCl3 in naphthalene at 180°C; further products;;
With sodium In neat (no solvent) heating of (C6H5)SiCl3 at 180°C; further products;;
With sodium In xylene heating of (C6H5)SiCl3 at 180°C; further products;;
With Na In neat (no solvent) heating of (C6H5)SiCl3 at 180°C; further products;;
With Na In further solvent(s) heating of (C6H5)SiCl3 in naphthalene at 180°C; further products;;
With Na In xylene heating of (C6H5)SiCl3 at 180°C; further products;;

  • 59
  • [ 694-53-1 ]
  • [ 1048-08-4 ]
  • [ 789-25-3 ]
  • [ 791-31-1 ]
YieldReaction ConditionsOperation in experiment
With potassium Sodium In diethyl ether (C6H5)SiH3 and Na-K-alloy in ether at room temp.; acidic hydrolysis;;
With Na-K In diethyl ether (C6H5)SiH3 and Na-K-alloy in ether at room temp.; acidic hydrolysis;;
  • 60
  • (CO)5WC(OEt)SiPh3 [ No CAS ]
  • [ 14040-11-0 ]
  • [ 74-85-1 ]
  • [ 18666-24-5 ]
  • [ 2294-99-7 ]
  • [ 789-25-3 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane byproducts: Ph3SiOEt, Ph3SiCH2OEt, Ph3SiOH; under N2 0.5-1.0 mmol W(CO)5C(OEt)SiPh3 in 5-20 ml dioxane was heated at 1 atm; not isolated, detected by NMR and chromato-mass spectroscopy;
  • 61
  • [ 3003-91-6 ]
  • [ 789-25-3 ]
  • [ 1048-08-4 ]
YieldReaction ConditionsOperation in experiment
In not given byproducts: (C6H5)(CH3)2CCOOH; (C6H5)3SiH and (C6H5)(CH3)2CK; carbonation; hydrolysis;;
In not given byproducts: (C6H5)(CH3)2CCOOH; (C6H5)3SiH and (C6H5)(CH3)2CK; carbonation; hydrolysis;;
  • 62
  • (CO)5CrC(OEt)SiPh3 [ No CAS ]
  • [ 94363-95-8 ]
  • [ 74-85-1 ]
  • [ 2294-99-7 ]
  • [ 13007-92-6 ]
  • [ 789-25-3 ]
YieldReaction ConditionsOperation in experiment
In melt byproducts: Ph3SiEt, Ph3SiOH, Ph3SiOEt; heated in partially evacuated closed tube at 85°C under N2; further by-products; sublimation Cr(CO)6, other products not isolated and detected by GLC,NMR and chromato-mass spectroscopy;
In 1,4-dioxane byproducts: Ph3SiOEt, Ph3SiEt; 0.5-1.0 mmol of (CO)5Cr(OEt)SiPh3 in 5-20 ml of dioxane was heated at 1 atm under N2; not isolated, detected by GLC, NMR and chromato-mass spectroscopy;
  • 63
  • (CO)5MoC(OEt)SiPh3 [ No CAS ]
  • C2H5C(O)Si(C6H5)3Mo(CO)3 [ No CAS ]
  • [ 18666-24-5 ]
  • [ 2294-99-7 ]
  • [ 199620-15-0 ]
  • [ 789-25-3 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane byproducts: Ph3SiOEt, Ph3SiOH, ethylene; 0.5-1.0 mmol (CO)5MoC(OEt)SiPh3 in 5-20 ml dioxane was heated at 1 atm under N2; further by-products; not isolated, detected by GLC, NMR and chromato-mass spectroscopy;
byproducts: ethylene, Ph3SiOEt, Ph3SiOH; heating at 85 °C in partially evacuated closed Schlenk tube under N2; further by-products; sublimation Mo(CO)6, other products not isolated and detected by NMR and chromato-mass spectroscopy;
  • 64
  • [ 789-25-3 ]
  • [ 1450-23-3 ]
YieldReaction ConditionsOperation in experiment
95% In N,N-dimethyl-formamide for 48h; UV-irradiation; 5 Examples 3 to 13 (Table 2, Run No.2 to No.12); Solutions of eleven monohydrosilanes (other than dimethylphenylsilane) in DMF with 4 mol % of CpFe(CO)2Me iron complex catalyst were prepared as shown in Table 2 and irradiated with ultraviolet radiation under a high-pressure mercury lamp. Reaction was carried out for varying times under the same conditions as in Example 1 except that the amount of iron complex catalyst was changed to 0.5 mmol only when the hydrosilane reactant was triphenylsilane. The results are shown in Table 2 together with the result of Example 1. It is evident from Table 2 that corresponding disilanes were produced in high yields of 50% to 100%.
95% With silver trifluoromethanesulfonate In tetrahydrofuran at 60℃; for 0.533333h; 2 The reaction formula of this embodiment is as follows: AgOTf (0.025 mmol, 0.0026 g) was added to the reaction flask, tetrahydrofuran (THF, 2.5 ml) was added, and then 2.5 mmol of compound 1c (0.6503 g) was slowly added dropwise to the reaction flask, and the reaction was stirred at 60 ° C for 30 minutes. After 2 minutes, the product 2c (0.6153 g) was distilled under reduced pressure after the reaction was completed, and the yield was 95%.
21% With lithium In diethyl ether byproducts: LiH; boiling of (C6H5)3SiH and Li in ether for several days;;
21% With Li In diethyl ether byproducts: LiH; boiling of (C6H5)3SiH and Li in ether for several days;;
Multi-step reaction with 2 steps 1: Br2 / tetrachloromethane 2: not given
Multi-step reaction with 2 steps 1: Br2 / tetrachloromethane 2: not given

  • 65
  • [ 7782-65-2 ]
  • [ 574-12-9 ]
  • [ 789-25-3 ]
  • Ge(C6H5)3*C6H5C9H5O2 [ No CAS ]
  • 66
  • [ 7440-31-5 ]
  • [ 574-12-9 ]
  • [ 789-25-3 ]
  • Sn(C6H5)3*C6H5C9H5O2 [ No CAS ]
  • 67
  • [ 593-66-8 ]
  • [ 789-25-3 ]
  • [ 18666-68-7 ]
YieldReaction ConditionsOperation in experiment
49% With potassium phosphate at 0℃; for 144h;
  • 68
  • [ 673-32-5 ]
  • [ 6728-26-3 ]
  • [ 789-25-3 ]
  • [ 1035485-07-4 ]
YieldReaction ConditionsOperation in experiment
88% With bis(1,5-cyclooctadiene)nickel(0); tricyclohexylphosphine In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 69
  • [ 637-69-4 ]
  • [ 789-25-3 ]
  • [ 1053281-68-7 ]
  • [ 1145706-49-5 ]
  • [ 1515-95-3 ]
  • 70
  • [ 789-25-3 ]
  • [ 1829-40-9 ]
  • [ 791-31-1 ]
YieldReaction ConditionsOperation in experiment
With water In ethyl acetate at 80℃; for 24h;
With water; 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In tetrahydrofuran at 0℃; for 3h; Schlenk technique; Glovebox;
59 %Chromat. With tert.-butylhydroperoxide; [CuΙ3(pz)3{PMo12O60}].H2O In water; acetonitrile at 60℃; for 1h;
  • 71
  • [ 71-43-2 ]
  • [ 789-25-3 ]
  • [ 1048-08-4 ]
YieldReaction ConditionsOperation in experiment
37% With norbornene; [Ir(hydride)2(1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene)(pyridine)3][BF4] In tetrahydrofuran at 110℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;
31% With 2,6-dimethylpyridine; trityl tetrakis(pentafluorophenyl)borate at 20℃; Inert atmosphere;
  • 72
  • [ 75-11-6 ]
  • [ 789-25-3 ]
  • [ 791-29-7 ]
YieldReaction ConditionsOperation in experiment
49% With triphenylgermane; triphenylstannane; triisobutylaluminum In hexane; dichloromethane at 20℃;
  • 73
  • [ 789-25-3 ]
  • [ 1048-08-4 ]
  • [ 1450-23-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Na-K / diethyl ether 2: diethyl ether 3: Na-K; C6H5Br / diethyl ether
  • 74
  • [ 111-87-5 ]
  • [ 455-32-3 ]
  • [ 789-25-3 ]
  • [ 94-50-8 ]
  • [ 379-50-0 ]
YieldReaction ConditionsOperation in experiment
81%; 68% With hydridotetakis(triphenylphosphine)rhodium(I); 1,2-bis-(diphenylphosphino)ethane; In chlorobenzene; at 20℃; for 3h;Inert atmosphere; General procedure: In a two-necked flask equipped with a reflux condenser were placed 2 (0.5 mmol, 54 mL), 4-methoxyphenol (0.5 mmol, 62 mg), triphenylsilane (0.5 mmol, 130 mg), RhH(PPh3)4 (1 mol%, 5.8 mg), 1,2-bis(diphenylphosphino)ethane (2 mol%, 4.0 mg) in chlorobenzene (1 mL) under an argon atmosphere, and the solution was stirred at room temperature for 3 h. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel giving p-methoxyphenyl benzoate (109.1 mg, 96%) and triphenylsilyl fluoride (121.1 mg, 87%) as colorless solid. Triphenylsilyl Fluoride Colorless solid. Mp. 64.0-65.0 C (hexane). Lit.8 64 C. 1H-NMR (400 MHz, CDCl3) d 7.41 (6H, t, J = 7.6 Hz), 7.48 (3H, t, J = 7.6 Hz), 7.65 (6H, dd, J = 7.6, 1.6 Hz). 13C-NMR (100 MHz, CDCl3) d 128.1, 130.8, 132.5 (d, J = 16.7 Hz), 135.0 (d, J = 2.3 Hz). IR (KBr) v 3051, 3025, 1429, 1124, 841 cm-1. MS (EI) m/z 278 (M+, 100%), 201 (M+-C6H5, 41%). HRMS Calcd for C18H15SiF: 278.0948. Found: 278.0927.
  • 75
  • [ 455-32-3 ]
  • [ 150-76-5 ]
  • [ 789-25-3 ]
  • [ 1523-19-9 ]
  • [ 379-50-0 ]
YieldReaction ConditionsOperation in experiment
96%; 87% With hydridotetakis(triphenylphosphine)rhodium(I); 1,2-bis-(diphenylphosphino)ethane; In chlorobenzene; at 20℃; for 3h;Inert atmosphere; In a two-necked flask equipped with a reflux condenser were placed 2 (0.5 mmol, 54 mL), 4-methoxyphenol (0.5 mmol, 62 mg), triphenylsilane (0.5 mmol, 130 mg), RhH(PPh3)4 (1 mol%, 5.8 mg), 1,2-bis(diphenylphosphino)ethane (2 mol%, 4.0 mg) in chlorobenzene (1 mL) under an argon atmosphere, and the solution was stirred at room temperature for 3 h. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel giving p-methoxyphenyl benzoate (109.1 mg, 96%) and triphenylsilyl fluoride (121.1 mg, 87%) as colorless solid. Triphenylsilyl Fluoride Colorless solid. Mp. 64.0-65.0 C (hexane). Lit.8 64 C. 1H-NMR (400 MHz, CDCl3) d 7.41 (6H, t, J = 7.6 Hz), 7.48 (3H, t, J = 7.6 Hz), 7.65 (6H, dd, J = 7.6, 1.6 Hz). 13C-NMR (100 MHz, CDCl3) d 128.1, 130.8, 132.5 (d, J = 16.7 Hz), 135.0 (d, J = 2.3 Hz). IR (KBr) v 3051, 3025, 1429, 1124, 841 cm-1. MS (EI) m/z 278 (M+, 100%), 201 (M+-C6H5, 41%). HRMS Calcd for C18H15SiF: 278.0948. Found: 278.0927.
  • 76
  • [ 606129-89-9 ]
  • [ 789-25-3 ]
  • [ 1097245-13-0 ]
  • 77
  • potassium phosphate [ No CAS ]
  • bis(tri-tert-butylphosphine)palladium(0) [ No CAS ]
  • [ 606129-89-9 ]
  • [ 789-25-3 ]
  • [ 1421001-67-3 ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-pyrrolidin-2-one; Example 26 Synthesis of Carbazole Derivative 17 9-Acetyl-3,6-diiodocarbazole (10.0 g) and triphenylsilane (12.4 g) were dry N-methylpyrrolidone (200 mL), followed by bubbling with argon gas for 30 min. Tripotassium phosphate (27.6 g) and bis(tri-t-butylphosphine)palladium (0.111 g) were added thereto, and the mixture was stirred at room temperature for 19 hours. The obtained reaction mixture was filtrated, and the filtrate was extracted with methylene chloride. The separated organic layer was washed with brine and dried, and the methylene chloride was evaporated. The residue was treated through silica gel column chromatography (eluent: toluene), to thereby obtain 1.97 g of 9-acetyl-3,6-bis(triphenylsilyl)carbazole as colorless powder.
  • 78
  • [ 14073-97-3 ]
  • [ 789-25-3 ]
  • [ 1441316-68-2 ]
  • [ 400784-70-5 ]
YieldReaction ConditionsOperation in experiment
13.043 % de With bis(1,5-cyclooctadiene)nickel (0); potassium <i>tert</i>-butylate; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 20℃; Inert atmosphere; Overall yield = 97 %; Overall yield = 201 mg; chemoselective reaction; 4.2 General procedure for nickel-catalyzed hydrosilylation of carbonyl compounds General procedure: To a round-bottom flask placed inside a glovebox were added Ni(COD)2 (0.10equiv), 1,3-bis-(2,4,6-trimethylphenyl)imidazolium hydrochloride (IMes·HCl) (0.10equiv), and potassium tert-butoxide (0.10equiv). The flask was then sealed with a rubber septum, removed from the glovebox, and placed under a positive nitrogen atmosphere. THF (1.5mL) was added and the resulting dark green/blue mixture was stirred for 15min at rt. This solution was then added via gas-tight syringe to a stirring solution of triphenylsilane (1.2equiv for hydrosilylation of simple ketones and 1.1equiv for hydroxy-ketones) and the corresponding carbonyl compound (1equiv) under nitrogen. The reaction mixture was stirred at rt and was monitored by TLC until total consumption of the corresponding carbonyl compound was noted. Upon completion, the reaction was exposed to air, silica gel was added, solvent was evaporated in vacuo, and the resulting residue was directly loaded on a silica column and purified.
  • 79
  • [ 20098-14-0 ]
  • [ 789-25-3 ]
  • 4-(triphenylsilyloxy)adamantan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With bis(1,5-cyclooctadiene)nickel (0); potassium tert-butylate; 1,3-bis(mesityl)imidazolium chloride; In tetrahydrofuran; at 20℃;Inert atmosphere; General procedure: To a round-bottom flask placed inside a glovebox were added Ni(COD)2 (0.10equiv), 1,3-bis-(2,4,6-trimethylphenyl)imidazolium hydrochloride (IMes·HCl) (0.10equiv), and potassium tert-butoxide (0.10equiv). The flask was then sealed with a rubber septum, removed from the glovebox, and placed under a positive nitrogen atmosphere. THF (1.5mL) was added and the resulting dark green/blue mixture was stirred for 15min at rt. This solution was then added via gas-tight syringe to a stirring solution of triphenylsilane (1.2equiv for hydrosilylation of simple ketones and 1.1equiv for hydroxy-ketones) and the corresponding carbonyl compound (1equiv) under nitrogen. The reaction mixture was stirred at rt and was monitored by TLC until total consumption of the corresponding carbonyl compound was noted. Upon completion, the reaction was exposed to air, silica gel was added, solvent was evaporated in vacuo, and the resulting residue was directly loaded on a silica column and purified.
  • 80
  • [ 20098-14-0 ]
  • [ 789-25-3 ]
  • 4-(triphenylsilyloxy)adamantan-1-ol [ No CAS ]
  • C46H44O2Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82%; 14% With bis(1,5-cyclooctadiene)nickel (0); potassium tert-butylate; 1,3-bis(mesityl)imidazolium chloride; In tetrahydrofuran; at 20℃; for 0.5h;Inert atmosphere; General procedure: To a round-bottom flask placed inside a glovebox were added Ni(COD)2 (0.10equiv), 1,3-bis-(2,4,6-trimethylphenyl)imidazolium hydrochloride (IMes·HCl) (0.10equiv), and potassium tert-butoxide (0.10equiv). The flask was then sealed with a rubber septum, removed from the glovebox, and placed under a positive nitrogen atmosphere. THF (1.5mL) was added and the resulting dark green/blue mixture was stirred for 15min at rt. This solution was then added via gas-tight syringe to a stirring solution of triphenylsilane (1.2equiv for hydrosilylation of simple ketones and 1.1equiv for hydroxy-ketones) and the corresponding carbonyl compound (1equiv) under nitrogen. The reaction mixture was stirred at rt and was monitored by TLC until total consumption of the corresponding carbonyl compound was noted. Upon completion, the reaction was exposed to air, silica gel was added, solvent was evaporated in vacuo, and the resulting residue was directly loaded on a silica column and purified.
  • 81
  • [ 7787-20-4 ]
  • [ 789-25-3 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
45.946 % de With bis(1,5-cyclooctadiene)nickel (0); potassium <i>tert</i>-butylate; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 20℃; Inert atmosphere; Overall yield = 98 %; Overall yield = 206 mg; chemoselective reaction; 4.2 General procedure for nickel-catalyzed hydrosilylation of carbonyl compounds General procedure: To a round-bottom flask placed inside a glovebox were added Ni(COD)2 (0.10equiv), 1,3-bis-(2,4,6-trimethylphenyl)imidazolium hydrochloride (IMes·HCl) (0.10equiv), and potassium tert-butoxide (0.10equiv). The flask was then sealed with a rubber septum, removed from the glovebox, and placed under a positive nitrogen atmosphere. THF (1.5mL) was added and the resulting dark green/blue mixture was stirred for 15min at rt. This solution was then added via gas-tight syringe to a stirring solution of triphenylsilane (1.2equiv for hydrosilylation of simple ketones and 1.1equiv for hydroxy-ketones) and the corresponding carbonyl compound (1equiv) under nitrogen. The reaction mixture was stirred at rt and was monitored by TLC until total consumption of the corresponding carbonyl compound was noted. Upon completion, the reaction was exposed to air, silica gel was added, solvent was evaporated in vacuo, and the resulting residue was directly loaded on a silica column and purified.
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