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CAS No. : | 778-24-5 | MDL No. : | MFCD00041326 |
Formula : | C14H16Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WJKVFIFBAASZJX-UHFFFAOYSA-N |
M.W : | 212.36 | Pubchem ID : | 136618 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 69.63 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.15 cm/s |
Log Po/w (iLOGP) : | 2.9 |
Log Po/w (XLOGP3) : | 4.85 |
Log Po/w (WLOGP) : | 2.51 |
Log Po/w (MLOGP) : | 4.41 |
Log Po/w (SILICOS-IT) : | 2.77 |
Consensus Log Po/w : | 3.49 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.67 |
Solubility : | 0.00452 mg/ml ; 0.0000213 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.58 |
Solubility : | 0.00553 mg/ml ; 0.0000261 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.8 |
Solubility : | 0.000337 mg/ml ; 0.00000159 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.75 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With bromine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With I2; AlI2 | |
With aluminium(III) iodide; iodine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nickel; methyl cyclohexane Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In not given |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: chlorobenzene With gallium(III) trichloride; magnesium Stage #2: dimethylsilicon dichloride In chlorobenzene at 70℃; for 8.5h; Further stages.; | |
With sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl ether Erhitzen des Reaktionsprodukts auf 150grad; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethyl sulfoxide In 1,4-dioxane at 5℃; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 14% 2: 54% | In cyclohexane for 1h; Ambient temperature; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 11.5% 2: 83.4% | In tetrahydrofuran at 90℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform-d1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.9% | In tetrahydrofuran at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tin(IV) chloride; nickel 1.) CH2Cl2, RT, 30 min; Multistep reaction. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tin(IV) chloride In dichloromethane for 0.5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 54% 2: 14% | With methanol In cyclohexane for 1h; Ambient temperature; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50 % Chromat. | In tetrahydrofuran 1.) -78 deg C, 30 min, 2.) RT, 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine)platinum In benzene at 150℃; for 22h; other alkene; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 34 % Chromat. 2: 19 % Chromat. 3: 3 % Chromat. 4: 13 % Chromat. | In tetrahydrofuran; hexane at -30 - 25℃; for 1h; | |
1: 34 % Chromat. 2: 19 % Chromat. 3: 21 % Chromat. 4: 3 % Chromat. | In tetrahydrofuran; hexane at -30 - 25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; hexane at -30 - 25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 12 % Chromat. 2: 16 % Chromat. | With acetophenone In benzene at 20℃; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 43 % Chromat. 2: 9 % Chromat. 3: 12 % Chromat. | In benzene at 20℃; Irradiation; | |
1: 6 % Chromat. 2: 13 % Chromat. 3: 17 % Chromat. | With triphenylene In benzene at 20℃; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 15% 2: 15% | In toluene at 160℃; for 120h; Further byproducts given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.5% | at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 10 % Spectr. 2: 25 % Spectr. 3: 10 % Spectr. | In tetrahydrofuran at 4℃; for 192h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 26 % Chromat. 2: 38 % Chromat. 3: 6 % Chromat. 4: 2.5 % Chromat. | With oxygen In tetrahydrofuran at 0℃; for 0.0166667h; Further byproducts given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 26 % Chromat. 2: 38 % Chromat. 3: 6 % Chromat. 4: 0.3 % Chromat. | With oxygen In tetrahydrofuran at 0℃; for 0.0166667h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 40℃; | ||
at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100 % Chromat. | With ammonia; iron(III) chloride; sodium amide at 20℃; for 0.05h; | |
98 %Chromat. | With potassium trimethylsilonate In dimethyl sulfoxide at 70℃; for 6h; Sealed tube; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With (hydridotris(3,5-dimethylpyrazolyl)borate)PtMe2H at 200℃; for 24h; | |
61% | 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With carbon dioxide; [(1,3-bis(3-tBu-5-Me-2-oxy-benzyl)-4-Me-MeOC6H2]Zr(CH2Ph)2; tris(pentafluorophenyl)borate In benzene-d6 at 20℃; for 0.25h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 6 % Chromat. 2: 6 % Chromat. 3: 11 % Chromat. | With aluminium trichloride at 110 - 120℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran; various solvent(s) / 6 h / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 74 percent / tetrahydrofuran; benzene-d6 / 16 h / Ambient temperature 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 2 steps 1: 38 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 2 steps 1: 38 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C |
Multi-step reaction with 3 steps 1: 0.3 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 2: tetrahydrofuran; various solvent(s) / 6 h / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 2 steps 1: 45 percent Spectr. / 1,2-dibromoethane / tetrahydrofuran; diethyl ether / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 3 steps 1: 35 percent / tetrahydrofuran / 1 h 2: 74 percent / N-bromosuccinimide / CCl4 / 48 h / Heating 3: 50 percent Chromat. / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) RT, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 74 percent / tetrahydrofuran; benzene-d6 / 16 h / Ambient temperature 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 2 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 38 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C |
Multi-step reaction with 2 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 6 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C | ||
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 38 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 4 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 0.3 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 3: tetrahydrofuran; various solvent(s) / 6 h / 0 °C 4: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 2 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 6 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C | ||
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 45 percent Spectr. / 1,2-dibromoethane / tetrahydrofuran; diethyl ether / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 2 steps 1: 59 percent / Li / tetrahydrofuran / 4 h 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C | ||
Multi-step reaction with 3 steps 1: 89 percent / NaHCO3, H2O / acetone / 1 h / 0 °C 2: tetrahydrofuran; various solvent(s) / 6 h / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90.5 percent / 0.5 h / 0 °C 2: 1.6 M nBuLi / tetrahydrofuran; hexane / 1) -40 deg C, 60 min, 2) to r.t., 60 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 74 percent / N-bromosuccinimide / CCl4 / 48 h / Heating 2: 50 percent Chromat. / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) RT, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 83.4 percent / tetrahydrofuran / 1 h / 90 °C 2: 3.9 percent / tetrahydrofuran / 2 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluorormethanesulfonic acid; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane | 17.A Step A: Step A: Preparation of 3-[3-(4-Fluorophenyl)-3-oxo-1-propenyl]-benzonitrile Triflic acid (3.2 g, 21 mmol) is added portionwise to diphenyldimethylsilane (2.22 g, 10.5 mmol) in 20 mL of dichloromethane and stirred for 1 hour. After cooling to -78° C., diisopropylethylamine (1.42 g, 11 mmol) and 4'-fluoroacetophenone (1.38 g, 10 mmol) are added and the reaction mixture stirred for another hour before adding 3-cyanobenzaldehyde (1.0 g, 7.62 mmol). After the reaction mixture is stirred 18 hours, it is diluted with 100 mL of dichloromethane and stirred 1 hour with a saturated solution of sodium bicarbonate. The organic layer is separated, dried (MgSO4), concentrated and columned over SiO2 eluding with dichloromethane to provide 0.8 g of the title compound; mp 170°-172° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 24.1% 2: 13.5% 3: 42.4% | In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h); further product: polymers; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 27% 2: 13.3% 3: 34.1% | 80°C, 31 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In not given |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17.5% | 100°C, 15 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With CH3MgBr In not given | |
With methyl magnesium iodide In not given | ||
With CH3MgI In not given |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In benzene (N2), dried solvents, room temp., gas evolution, Pd separates; SiMe2Ph2detected by GC, Si2Me2Ph4 is not formed; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Na In not given |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0% | In tetrahydrofuran byproducts: naphthalene; sealed glass ampule with (C10H8)2Cr, Ph2SiMe2 and dried THF was heated in a boiling water bath for 1 h with occasional agitation; under rigorous exclusion of the atmosphere; evapd., naphthalene and byproducts were removed by vac. sublimation, final residue was carefully sublimed yielding the mixt. of the products, total yield 16%; high-resolution mass spectral anals.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In neat (no solvent) byproducts: benzene; High Pressure; heating of (CH3)3Si(C6H5) at 300°C and 100 atm H2 pressure;; | ||
With H2 In neat (no solvent) byproducts: benzene; High Pressure; heating of (CH3)3Si(C6H5) at 300°C and 100 atm H2 pressure;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 82.9% 2: 0% 3: 0% | With P(C6H5)2CH3 In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h) with addn. of diphenylmethylphosphine (8 equiv. per Pt-complex); further products: polymers; detn. by GLC; | |
1: 81.3% 2: 0% 3: 0% | With P(C6H5)2CH3 In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h) with addn. of diphenylmethylphosphine (2 equiv. per Pt-complex); further products: polymers; detn. by GLC; | |
1: 65.6% 2: 12.6% 3: 5.2% | With P(C6H5)2CH3 In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h) with addn. of diphenylmethylphosphine (0.5 equiv. per Pt-complex); further products: polymers; detn. by GLC; |
1: 50.3% 2: 27.2% 3: 12% | With P(C5H6)2CH3 In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h); further products: polymers; detn. by GLC; | |
1: 48.7% 2: 28.6% 3: 19.1% | In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h); further products: polymers; detn. by 1H-NMR; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 3% 2: 4% 3: 14% 4: 54% | With methanol In benzene Irradiation (UV/VIS); irradiation of catenate in benzene containing an excess of methanol with a 110 W low pressure Hg arc lamp at room temp. under Ar for 1-4 h; identification by GC and GC-MS; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With C6H5MgBr In not given |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 42% 2: 5% | In 1,4-dioxane refluxing for 6.5 h (N2), evapn.; trituration, extn., filtered, pptn. of mono complex on cooling of filtrate, working up of residue from extn. gave bis complex; elem. anal.; | |
1: 26% 2: 7% | In 1,4-dioxane Ar-atmosphere; refluxing for 6 h; evapn. (vac.), chromy. (Al2O3, CH2Cl2/petroleum ether), recrystn. (hexane); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | In tetrahydrofuran; diethylene glycol dimethyl ether heating at 150°C for 61 h (N2), chromy on silica gel (benzene), concn., pptn. with hexane, filtration, washing with hexane, drying in vac.; sepn. of mono complex by sublimation, chromy. on silica gel (benzene), concn., pptn. with hexane, washing with hexane, drying in vac., soln. in hot CHCl3, crystn. on addn. of petroleum ether and cooling; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | In hexane; n-heptane Ar-atmosphere; stoich. amts., refluxing in hexane/heptane=2:1 v/v for 24h; chromy. (Al2O3, CH2Cl2/petroleum ether), recrystn. (hexane); elem. anal.; | |
In hexane Ar-atmosphere; stoich. amts., refluxing; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: dimethyl(phenyl)silyl lithium; dimethyl zinc(II) In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: 1-Bromo-2-iodobenzene In tetrahydrofuran; hexane at 20℃; for 16h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In benzene-d6 for 20h; UV-irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C14H19Si2(1+)*C24BF20(1-) at -10 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: diphenylether With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at 20℃; for 16h; Inert atmosphere; Stage #2: Dimethyldiphenylsilane In tetrahydrofuran; diethyl ether; hexane at 20℃; for 16.67h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: H2 / neat (no solvent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 0.166667h; Inert atmosphere; Stage #2: bromobenzene In 1,2-dimethoxyethane at 30℃; | ||
Stage #1: bromobenzene With potassium methanolate; chlorobenzene In 1,2-dimethoxyethane at 30℃; for 0.0833333h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane In 1,2-dimethoxyethane at 30℃; for 0.0166667h; Inert atmosphere; Glovebox; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C70H92K4Li2O7; toluene In tetrahydrofuran at -78 - -40℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: phenyldimethylsilyl chloride In tetrahydrofuran at -40 - 20℃; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In toluene at 80℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 80℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: benzyl methyl diphenylsilane; methyllithium In tetrahydrofuran; diethyl ether at -78 - -30℃; for 20h; Stage #2: With deuteromethanol In tetrahydrofuran; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69 %Chromat. | In tetrahydrofuran at 30℃; for 1h; Inert atmosphere; | Typical Procedure for Silyl Substitution Reaction with SilyllithiumReagent General procedure: vial with a screw cap and a silicon-coated rubber septum wasconnected to a vacuum/nitrogen manifold through a needle,and it was evacuated and refilled with nitrogen three times. Dimethylphenylsilyllithium (0.4 M in THF, 2.5 mL, 2.0 equiv)was added to the vial under nitrogen atmosphere. 1-Bromo-3,5-dimethylbenzene (93.5 mg, 0.51 mmol) was added to the vial,then stirred at 30 °C. After 1 h, the reaction mixture was analyzedby GC to check completeness of the reaction. When thereaction was complete, H2O was added and the mixture wasextracted three times with Et2O. The organic layer was washedwith water and the combined organic layer was then dried overMgSO4 followed by filtration and evaporation. The crudeproduct was purified by silica-gel column chromatography with hexane eluent, then further purified by gel permeation chromatographyto give 3da in 63% isolated yield (76.5 mg, 0.318mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 48% 2: 8% | In tetrahydrofuran at 30℃; for 1h; Inert atmosphere; | Typical Procedure for Silyl Substitution Reaction with SilyllithiumReagent General procedure: vial with a screw cap and a silicon-coated rubber septum wasconnected to a vacuum/nitrogen manifold through a needle,and it was evacuated and refilled with nitrogen three times. Dimethylphenylsilyllithium (0.4 M in THF, 2.5 mL, 2.0 equiv)was added to the vial under nitrogen atmosphere. 1-Bromo-3,5-dimethylbenzene (93.5 mg, 0.51 mmol) was added to the vial,then stirred at 30 °C. After 1 h, the reaction mixture was analyzedby GC to check completeness of the reaction. When thereaction was complete, H2O was added and the mixture wasextracted three times with Et2O. The organic layer was washedwith water and the combined organic layer was then dried overMgSO4 followed by filtration and evaporation. The crudeproduct was purified by silica-gel column chromatography with hexane eluent, then further purified by gel permeation chromatographyto give 3da in 63% isolated yield (76.5 mg, 0.318mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); o-tetrachloroquinone In chloroform at 60℃; for 10h; Inert atmosphere; | 3. General procedure for homocoupling reaction by Pd/o-chloranil catalysis General procedure: To a screw-capped glass tube containing a magnetic stirrer bar were addedaryltrimethylsilane 1 (0.30 mmol, 1.0 equiv), Pd(CH3CN)4(BF4)2 (3.3 mg, 0.075 mmol, 2.5mol%), CHCl3 (1.5 mL) or CHCl3/1,2-dichloroethane (1:4, 1.5 mL) and o-chloranil (55.9 mg, 0.225 mmol, 0.75 equiv) under a stream of nitrogen. After stirring at 60 °C for 10 hours, thereaction mixture was cooled to room temperature, and then passed through a short pad of silicagel (eluent: CHCl3). After the organic solvent was removed under reduced pressure, the residuewas purified by flash column chromatography on silica gel to yield biaryl 2. The reactions wereconducted in 0.50 mmol scale for 1a in 2.5 mL of CHCl3, 0.30 mmol scale for 1b-1t in 1.5 mLof the indicated solvent, and 0.20 mmol scale for 1w in the indicated solvent, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With (DrewPhos)<SUB>2</SUB>PdI<SUB>2</SUB> In diethyl ether at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: phenyldimethylsilyl chloride With lithium In tetrahydrofuran at 0℃; for 6h; Inert atmosphere; Stage #2: fluorobenzene In tetrahydrofuran at -25℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With lithium acetate In N,N-dimethyl acetamide at 100℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With bis(1,5-cyclooctadiene)nickel(0); 1,10-Phenanthroline In toluene at 160℃; for 18h; Glovebox; Inert atmosphere; Sealed tube; | |
83% | With bis(1,5-cyclooctadiene)nickel (0); tributylphosphine; zinc In toluene for 36h; Inert atmosphere; Sealed tube; Heating; |