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Chemical Structure| 1075719-87-7
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Product Details of [ 1075719-87-7 ]

CAS No. :1075719-87-7 MDL No. :MFCD18643353
Formula : C14H21BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :RWANCHDMVNWYHW-UHFFFAOYSA-N
M.W : 232.13 Pubchem ID :59788424
Synonyms :

Safety of [ 1075719-87-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1075719-87-7 ]

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

  • Downstream synthetic route of [ 1075719-87-7 ]

[ 1075719-87-7 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 25309-64-2 ]
  • [ 25015-63-8 ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
96% With magnesium; triethylamine; In tetrahydrofuran; for 15h;Reflux; Example 1Preparation of pinacol ester of 4-ethylphenylboronic acid In a 2 necks Schlenk type flask, provided with a magnetic stirring bar and topped by a coolant, 4-ethylbenzene iodide (0.232 g, 1 mmol), pinacolborane (0.128 g, 1 mmol) and triethylamine (59 mg, 1 mmol) are added to 10 ml of a distilled THF solution containing magnesium turnings (24 mg, 1 mmol). The reactive mixture is stirred for approximately 15 hours at THF reflux.At the end of the reaction, the crude reaction product is hydrolyzed by 20 ml of neutral water and extracted by diethyl ether (3×40 ml). The joined organic phases are washed by 2×50 ml of neutral water then dried on MgSO4. After solvent evaporation, the obtained yield is of 96% with a total conversion of the starting iodide (yield/conversion of 96%). The resulting boronic ester is analyzed by GC, NMR 1H and 13C and GC/MS.Characterizations:NMR 1H, 7.74 (2H, D, 3 Hz); 7.22 (2H, D, 3 Hz); 2.66 (2H, Q, 3 Hz); 1.34 (12H, s); 1.24 (3H, T, 3 Hz).NMR 13C, 146.68; 133.87; 127.23; 126.31; 82.58; 28.08; 23.82; 14.42.Mass spectrometry: 232-231 (M+, 6-2%); 217-216 (8-2%); 147 (19%); 146-145 (71-15%); 134 (17%); 133 (100%); 132-131 (63-21%); 118 (18%); 117 (51%); 116-115 (17-4%); 105 (18%); 104 (10%); 91 (11%); 85 (14%); 77-76 (9-2%).Ultimate Analyses:calculated %: C: 72.44%; H: 9.12%; B: 4.66%.obtained %: C: 70.22%; H: 9.25%; b: 4.39%.
  • 2
  • [ 1585-07-5 ]
  • [ 61676-62-8 ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
90% With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -60℃;
87% With n-butyllithium In tetrahydrofuran; hexane at -60℃; Flow reactor;
  • 3
  • [ 1585-07-5 ]
  • [ 25015-63-8 ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(cyclopentadienyl)titanium dichloride; lithium methanolate In neat (no solvent) for 0.5h; Inert atmosphere; Glovebox; Stage #2: 1-bromo-4-ethylbenzene In neat (no solvent) at 100℃; for 24h; Sealed tube;
With iodine; magnesium In tetrahydrofuran at 25℃; Inert atmosphere;
  • 4
  • [ 1585-07-5 ]
  • [ 73183-34-3 ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
94.8% With palladium diacetate; triphenylphosphine; cesium pivalate In 1,4-dioxane at 95℃; for 2h; Inert atmosphere; 2; 2 Example 2 Under the protection of nitrogen, 1.85g p-ethyl bromobenzene (10mmol) and 6.35g bis(pinacolato)diboron (25mmol),Dissolve in 50mL 1,4-dioxane, and then dissolve 2.57g cesium pivalate (11mmol),113mg Pd(OAc)2 (0.5mmol) and 262mg PPh3 (1mmol) in 1,4-dioxane (30ml) solution,Add to the above solution, the reaction heat is raised to 95°C, and the reaction is stirred for 2h.The reaction solution was filtered through celite, the filtrate was collected, and the filtrate was concentrated under reduced pressure.Then silica gel column chromatography (eluent: petroleum ether volume: ethyl acetate volume = 10:1),The product was 2.20 g, the yield was 94.8%, and the purity was 99.2% (HPLC).
78% With potassium carbonate In toluene Inert atmosphere; Reflux; 16 2-(4-Etiiylphenyl)-4,4,5,5-tetramethyl-1,3,2-dloxaborolane (CP-11): Pd(PPh3)4 (1.5 g) was added to a mixture of l-bromo-4-ethylbenzene (CP- 10) (1.0.0 g, 54 mmol), pinacolatodlboron (9.5 g, 54 mmol) and potassium carbonate (15.3 g, 0.11 mol) in toluene (200 mL) under nitrogen protection. The mixture was refluxed overnight. After the mixture was cooled to room temperature, the solvent was removed under vacuum. To the residue were added water (200 mL) and ethyl acetate (200 mL). The organic phase was collected, and the aqueous phase was extracted with ethyl acetate (200 mL x 2). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to afford CP-11 (9.8 g, 78% yield). H NMR (CDCi,, 300 MHz) δ: 7.69 (d, J = 8.4 Hz, 2H, Ph), 7.08 (d, J = 8.4 Hz, 2H, Ph), 2.54 (q, J = 6.1 Hz, 2H, CH2), 1.22 (s, 12H, plnacol-CH3), 1.13 (m, 3H, CH3).
73% With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate In 1,4-dioxane at 110℃; for 10h; chemoselective reaction; General Procedure for Miyaura Borylation General procedure: Aryl/heteroaryl bromide 1 (1 mmol), B2pin2(2), B2npg2(4) orBpin (6, 1.2 mmol), and dioxane (5 mL) are taken into a 25 mLround-bottomed flask. KOAc (2 mmol) was added and stirredthe resultant mixture at room temperature for 5 min, PdII-TpTP(0.15 mol%) was added, and the contents were refluxed on preheatedoil bath at 110 °C under constant stirring in open-air.The reaction progress was ensured by TLC. After completion ofthe reaction, the mixture was cooled, dilute with water (20 mL)and extracted with tertbutylmethyl ether (3 × 10 mL). The combinedn-hexane layers were concentrated, and the crudeproduct obtained was purified by column chromatography (CC)on silica gel using a mixture of ethyl acetate and hexane (1:30)as eluent.
  • 5
  • [ 1075719-87-7 ]
  • [ 1401625-47-5 ]
  • [ 1401625-54-4 ]
YieldReaction ConditionsOperation in experiment
71% With sodium carbonate In 1,4-dioxane Inert atmosphere; Reflux; 16 tert-Butyl (S)-1 -((J/^2A?)-1 -cyano-2-(4'-ethylblphenyl-4-yl)cyclopropylamlno)-1 -oxobutan-2- ylcarbamate (CP-14-(S,«,/?)): PdCI2(dppf)2 (0.1 g) was added to a mixture of CP-8-(S,R,R) (0.8 g, 1.9 mmol), CP-11 (1.9 mL, 2 ) and aqueous sodium carbonate solution (1.9 mL, 2 M) In 1,4-dioxane (30 mL) under nitrogen protection. The mixture was refluxed overnight. After the mixture was cooled to room temperature, the solvent was removed under vacuum. To the residue were added water (50 mL) and ethyl acetate (50 mL). The organic phase was collected, and the aqueous phase was extracted with ethyl acetate (50 mL x 2). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by HPFC (PE:EA = 3:1) to afford CP-14-(S,R,R) (0.6 g, 71% yield). LC- MS: 448.1 [M+H]+.
  • 6
  • [ 1075719-87-7 ]
  • [ 1401625-47-5 ]
  • [ 1401624-48-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / 1,4-dioxane / Inert atmosphere; Reflux 2: formic acid / 4 h / 20 °C
YieldReaction ConditionsOperation in experiment
99% Stage #1: With iodine; magnesium In tetrahydrofuran at 25℃; for 3.083h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0 - 25℃; for 0.666667h; EXAMPLE 3 Preparation of Aryl and Alkyl-Pinacolboranate Esters Under Barbier-Type Conditions General procedure: EXAMPLE 3Preparation of Aryl and Alkyl-Pinacolboranate Esters Under Barbier-Type Conditions[0075] The following procedure for the preparation m-tolyl pinacolborane isrepresentative. A 25-mL round-bottom flask equipped with a magnetic stir bar was charged with magnesium turnings (0.058 g, 2.4 mmol) and was activated by addition of iodine crystals and warming until iodine sublimed. The flask was cooled to 25 °C and was purged with Ar. THF (3.5 mL) was added to the flask, followed by the addition of neatpinacolborane (0.29 mL, 2.0 mmol). m-Tolyl bromide (0.243 mL, 2.0 mmol) was then added drop wise over five minutes with constant stirring at 25 °C. The reaction was complete after 3 h as evidenced by the disappearance of pinacolborane starting material ( +27.7, d, J=173.9 Hz), and the appearance of a singlet at +30.6 ppm via nB-NMR. The reaction was then cooled to 0°C (ice bath) and acidified with 3 M aqueous HC1 (3 mL) (CAUTION: hydrogen evolution). After 10 min of stirring the reaction mixture was warmed to 25 °C and stirred for an additional 30 min. Table entries 4, 6, 7, 8 were quenched with aqueous NH C1 (2.5 mL, 0.16 M). The reaction mixture was then transferred to a separatory funnel and extracted with diethyl ether (3 x 15 mL). The combined organic layers were dried over anhydrous MgS04, filtered, and dried under vacuo (25°C, 1 Torr) to afford m-tolyl pinacolborane as a pale yellow oil. The results for the other pinacolborane esters prepared by this method are summarized in Table 2.
  • 8
  • [ 58530-53-3 ]
  • [ 1075719-87-7 ]
  • [ 1514914-34-1 ]
YieldReaction ConditionsOperation in experiment
84% With palladium diacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; at 70℃; for 24h;Inert atmosphere; General procedure: <strong>[58530-53-3]2,4-dibromopyridine</strong> (0.12 g, 0.50 mmol), phenylboronic acid pinacol ester (0.11 g, 0.55 mmol), KOH (56 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (52 mg, 20 mol %) were dissolved in CH3CN (6 mL). The reaction was stirred at 70 C under nitrogen atmosphere for 24 h and then cooled. The solid was filtrated off and the filtrate was concentrated. The crude product was then dissolved in CH2Cl2 (10 mL) and the solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon evaporation, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give 3w (104 mg, 89%) as a colorless liquid.
  • 9
  • [ 100-41-4 ]
  • [ 25015-63-8 ]
  • [ 1075719-87-7 ]
  • [ 1075719-83-3 ]
YieldReaction ConditionsOperation in experiment
With bis(1,2-bis(dimethylphosphino)ethane)dimethyliron In neat (no solvent) at 20℃; for 72h; Glovebox; Schlenk technique; Inert atmosphere; Irradiation; Overall yield = 73 %; Overall yield = 85 mg; regioselective reaction;
With C47H55N2Ni at 100℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Overall yield = 82 percent;
  • 10
  • [ 100-41-4 ]
  • [ 25015-63-8 ]
  • [ 1075719-87-7 ]
  • [ 1075719-83-3 ]
  • 2-(2-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 174090-36-9 ]
YieldReaction ConditionsOperation in experiment
1: 1 %Chromat. 2: 22 %Chromat. 3: 12 %Chromat. 4: 15 %Chromat. With bis(1,5-cyclooctadiene)nickel(0); 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; sodium t-butanolate at 100℃; for 20h; Inert atmosphere; Overall yield = 50 %; Overall yield = 145 mg;
  • 11
  • [ 1075719-87-7 ]
  • [ 134856-58-9 ]
  • 4-ethyl-1-(4-(trimethylsilylethynyl)phenyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 65℃; for 5h; Inert atmosphere;
  • 12
  • [ 1075719-87-7 ]
  • C33H36N2O3S2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / tetrahydrofuran; water / 5 h / 65 °C / Inert atmosphere 2.1: Rh<SUB>2</SUB>(S-N-(1,8-naphthoyl)alanine)<SUB>4</SUB> / methanol; 1,1,2,2-tetrachloroethane / 0.08 h / Molecular sieve; Inert atmosphere; Sealed tube 2.2: 72 h / -78 - -35 °C / Molecular sieve; Inert atmosphere; Sealed tube
  • 13
  • [ 1075719-87-7 ]
  • C36H32N2O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / tetrahydrofuran; water / 5 h / 65 °C / Inert atmosphere 2.1: Rh<SUB>2</SUB>(S-N-(1,8-naphthoyl)alanine)<SUB>4</SUB> / methanol; 1,1,2,2-tetrachloroethane / 0.08 h / Molecular sieve; Inert atmosphere; Sealed tube 2.2: 72 h / -78 - -35 °C / Molecular sieve; Inert atmosphere; Sealed tube 2.3: 70 °C / Molecular sieve; Inert atmosphere; Sealed tube
  • 14
  • [ 1075719-87-7 ]
  • C40H34N2O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / tetrahydrofuran; water / 5 h / 65 °C / Inert atmosphere 2.1: Rh<SUB>2</SUB>(S-N-(1,8-naphthoyl)alanine)<SUB>4</SUB> / methanol; 1,1,2,2-tetrachloroethane / 0.08 h / Molecular sieve; Inert atmosphere; Sealed tube 2.2: 72 h / -78 - -35 °C / Molecular sieve; Inert atmosphere; Sealed tube 2.3: 70 °C / Molecular sieve; Inert atmosphere; Sealed tube
  • 15
  • [ 100-41-4 ]
  • [ 73183-34-3 ]
  • [ 1075719-87-7 ]
  • [ 1075719-83-3 ]
  • C20H32B2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% With (6,6’-dimethoxy-[1,1 ‘-biphenyl]-2,2’-diyl)bis(bis(3 ,5-dimethyl-phenyl)phosphine); [(1,5-cyclooctadiene)(OH)iridium(I)]2 In hexane at 85℃; for 20h; Inert atmosphere; Glovebox; Sealed tube; Overall yield = 80 %; regioselective reaction;
  • 16
  • [ 1585-07-5 ]
  • 2-(4-iodobutoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
88% With magnesium In tetrahydrofuran at 25℃; for 3h; Inert atmosphere; General procedure for the synthesis of compounds 1a-1m General procedure: To a solution containing 4-IboxBpin (0.651 g,2.0 mmol) and anhydrous THF (8 mL) under Ar, Mg turnings (0.048 g,2.0 mmol) were added. The corresponding halide reagent (2.0 mmol) wasthen introduced dropwise over 5 min with constant stirring at 25 C. Thereaction was complete after 3 h, as evidenced by the disappearance of4-IboxBpin (d +21.6) via 11B NMR. 1 M HCl (3 mL) was then added to thereaction flask and left to stir for 5 min. The reaction mixture was thentransferred to a separatory funnel and extracted with diethyl ether(3 15 mL). The combined organic layers were dried over anhydrous MgSO4,filtered, and dried in vacuo, (25 C, 1 Torr) to afford the correspondingpinacolboronate.
  • 17
  • [ 25015-63-8 ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pentane / 0.5 h / 25 °C / Inert atmosphere 2: pentane / 3 h / 25 °C / Inert atmosphere 3: magnesium / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere
  • 18
  • C6H12BIO2 [ No CAS ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pentane / 3 h / 25 °C / Inert atmosphere 2: magnesium / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere
  • 19
  • [ 1075719-87-7 ]
  • [ 123-07-9 ]
YieldReaction ConditionsOperation in experiment
94% With [Cu6I24-I)24-5-phpymt)2]; triethylamine In water; acetonitrile for 48h; UV-irradiation;
  • 20
  • [ 1075719-87-7 ]
  • methyl 4-(bromo(trifluoromethoxy)methyl)benzoate [ No CAS ]
  • (R)-methyl 4-((4-ethylphenyl)(trifluoromethoxy)methyl)benzoate [ No CAS ]
  • methyl 4-((4-ethylphenyl)(trifluoromethoxy)methyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84 % ee Stage #1: 2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With nickel(II) bromide dimethoxyethane; n-butyllithium; (3aR,8aS)-2-(3-methylpyridin-2-yl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazole In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: methyl 4-(bromo(trifluoromethoxy)methyl)benzoate In tetrahydrofuran; hexane at 0℃; for 5h; Inert atmosphere; Glovebox; Schlenk technique; Overall yield = 82 %; Overall yield = 139 mg; enantioselective reaction;
  • 21
  • [ 29786-93-4 ]
  • [ 1075719-87-7 ]
  • C18H30BO2(1-)*Li(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With nickel(II) bromide dimethoxyethane; (3aR,8aS)-2-(3-methylpyridin-2-yl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazole In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere; Glovebox; Schlenk technique;
In tetrahydrofuran; hexane at 20℃; for 1h;
  • 22
  • [ 73183-34-3 ]
  • [ 117357-15-0 ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
87% With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 20℃; Glovebox; Inert atmosphere;
  • 23
  • [ 1075719-87-7 ]
  • [ 174680-55-8 ]
  • 3-benzyl-5-(4-ethylphenyl)pyrazine-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 12h; Inert atmosphere; 14.14-1 Synthesis Example 14-1 Under a nitrogen atmosphere, 3-benzyl-5-bromopyrazine-2-amine (100.0 mg, 0.3 mmol, 1 eq.) and 2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (140.4 mg, 0.6 mmol, 1.6 eq.) were dissolved in ethanol (1 ml) and toluene (6 ml). To the solution was added 1 M aqueous sodium carbonate solution (1.6 ml) and the mixture was stirred at room temperature. The reaction solution was degassed under vacuum. To the solution was added a catalytic amount of tetrakis(triphenylphosphine)palladium (0) (about 1 cup of micro spatula) and the mixture was degassed again under vacuum and then stirred at 100° C. overnight (12 hours). After allowing the mixture to cool to room temperature, the mixture was filtered through Celite to remove palladium catalyst. The resulting residue was extracted with ethyl acetate, washed with distilled water and saturated brine, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (eluent: hexane/ethyl acetate=7/3) to obtain 3-benzyl-5-(4-ethylphenyl)pyrazine-2-amine as a yellow solid (100.4 mg, 0.3 mmol, 91%). 1H-NMR (500 MHz, CDCl3): δ (ppm)=8.37 (s, 1H), 7.86 (d, J=8.0 Hz, 2H), 7.33-7.25 (m, 7H), 4.37 (s, 2H), 4.18 (s, 2H), 2.70 (t, J=7.4 Hz, 2H), 1.28-1.25 (m, 3H). 13C-NMR (150 MHz, CDCl3): δ (ppm)=15.78, 28.79, 41.42, 76.90, 77.16, 77.41, 125.91, 127.16, 128.48, 128.71, 129.11, 134.87, 136.95, 137.44, 140.67, 142.96, 144.47, 151.66.
  • 24
  • [ 1075719-87-7 ]
  • C28H25N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 12 h / 100 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / 21 h / 0 - 80 °C / Inert atmosphere
  • 25
  • [ 1075719-87-7 ]
  • C28H25N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 12 h / 100 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / 14 h / 0 - 80 °C / Inert atmosphere
  • 26
  • [ 100-41-4 ]
  • [ 73183-34-3 ]
  • [ 1075719-87-7 ]
  • [ 1075719-83-3 ]
YieldReaction ConditionsOperation in experiment
With C35H59FeNP2 at 100℃; for 18h; Schlenk technique; Glovebox; Inert atmosphere; Overall yield = 28 %;
  • 27
  • C20H17S2(1+)*CF3O3S(1-) [ No CAS ]
  • [ 73183-34-3 ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
86% With dmap; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In acetonitrile at 20℃; for 8h; Irradiation; Inert atmosphere;
36 mg With palladium diacetate; sodium pivalate; XPhos In dichloromethane; acetone at 20℃; for 12h; Inert atmosphere;
  • 28
  • [ 100-41-4 ]
  • [ 1075719-87-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 1 h / -40 - 20 °C 2: dmap; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile / acetonitrile / 8 h / 20 °C / Irradiation; Inert atmosphere
Multi-step reaction with 2 steps 1: dichloromethane / 1.5 h / -40 - 20 °C / Schlenk technique; Inert atmosphere 2: palladium diacetate; XPhos; sodium pivalate / acetone; dichloromethane / 12 h / 20 °C / Inert atmosphere
  • 29
  • [ 100-41-4 ]
  • [ 73183-34-3 ]
  • [ 1075719-87-7 ]
  • [ 1075719-83-3 ]
  • 2-(2-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 165904-22-3 ]
YieldReaction ConditionsOperation in experiment
With basolite C300 In neat (no solvent) at 100℃; for 24h; 2.4. Experimental procedure General procedure: In a 25 mL round bottom flask, toluene (1 mL), Cu3(BTC)2 (30 mg),1 (127 mg, 0.5 mmol) were charged and this slurry was stirred at 100°C. The borylation of toluene was monitored by gas chromatography(GC) and the conversion of 1 was determined at different time intervals.Similar experimental procedures were performed with radicalquenchers like TEMPO and 2,6-di-t-butyl-4-methylphenol with appropriateamount mentioned in the table. The product identity was confirmedby analyzing the reaction mixture by GC-MS. Conversion of theborylation reaction and selectivity of the products were determined byAgilent GC.
  • 30
  • [ 459-47-2 ]
  • [ 73183-34-3 ]
  • [ 1075719-87-7 ]
  • [ 100-41-4 ]
YieldReaction ConditionsOperation in experiment
68%; 22%Chromat. With tetramethylammonium fluoride; 2-mercaptopyridine sodium salt; In acetonitrile; at 30 - 35℃; for 24h;Irradiation; Inert atmosphere; General procedure: To a 9 mL snap vial with magnetic stirring bar, B2pin2 (0.6 mmol), TMAF (0.6 mmol), sodiumpyridine-2-thiolate (30 mol%) were added. The vial was evacuated and back filled with N2 for threetimes. A solution of fluoroarene (0.2 mmol) in dry MeCN (2 mL) was added by syringe. The mixturewas irradiated with a 385-390 nm LED (with aluminum block cooling to keep the internaltemperature of the reaction mixture at 30-35 oC) under N2 atmosphere. After 24 h, the reactionmixture was diluted with EA (5 mL) and filtered through a pad of Celite. After filtration, the filtratewas concentrated under reduced pressure. The residue was purified by silica gel columnchromatography (eluent: hexane/EtOAc) to give the corresponding boronate esters.
  • 31
  • [ 1075719-87-7 ]
  • C17H28N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; hexane / 1 h / 20 °C 2: copper(I) bromide / tetrahydrofuran; hexane / 1 h / 20 °C
  • 32
  • [ 1075719-87-7 ]
  • [ 171364-81-1 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride In water; acetonitrile at 20℃; for 8h; Irradiation;
  • 33
  • [ 100-41-4 ]
  • [ 25015-63-8 ]
  • [ 1075719-87-7 ]
  • [ 1075719-83-3 ]
  • C20H32B2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(η4-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I); 2’,7’-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-diaza-9,9’-spirobifluorene In 1,4-dioxane at 90℃; for 16h; regioselective reaction;
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