Structure of 504433-86-7
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| CAS No. : | 504433-86-7 |
| Formula : | C14H18BFO2 |
| M.W : | 248.10 |
| SMILES Code : | CC1(C)C(C)(C)OB(/C=C/C2=CC=C(F)C=C2)O1 |
| English Name : | (E)-2-(4-Fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
| MDL No. : | MFCD12546189 |
| InChI Key : | ZJRAXVMUDOVAOD-MDZDMXLPSA-N |
| Pubchem ID : | 11207378 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 81% | With oxygen at 95℃; for 9h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 45% | With NaOC(CH3)3; CH3OH In tetrahydrofuran 1.0 mol% Cu-complex, alkyne, diborane, NaOC(CH3)3, CH3OH, THF, -15°C, 24 h, N2 atm.; 87:13 ratio of isomers; | |
| Stage #1: bis(pinacol)diborane With C178H184ClCuN2O33; potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-ethynyl-4-fluorobenzene In tetrahydrofuran; methanol at -20℃; for 16h; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 97% | With Lithium 1,1,1,3,3,3-hexamethyldisilazide In toluene at 80℃; for 24h; Inert atmosphere; | 6 Preparation method: Under the protection of nitrogen, add raw material 4-fluorophenylacetylene (0.5mmol), pinacol borane (0.6mmol), catalyst LHMDS (7mol%) and organic solvent toluene (0.5mL) into the reaction vessel and stir and mix, After mixing uniformly, react at 80°C for 24h, filter and purify to obtain the product; the product separation yield is 97%. |
| 95% | at 60℃; for 16h; Inert atmosphere; Schlenk technique; | |
| 94% | With borane-THF In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; regioselective reaction; | General procedure: Phenylacetylene (1.00 mmol, 0.110 mL), pinacolborane (1.10 mmol, 0.160 mL) and H3B·THF (0.100 mmol, 1 M, 0.100 mL) were added sequentiallyto a sealed reaction vial flushed with an nitrogen atmosphere. The reaction mixture was stirred for 1 h at 60 °C. The reaction was then quenched by filtration through a short silica plug (5 cm) with CH2Cl2. The solvents were removed under reduced pressure and the residue was purified by flash column chromatography (SiO2; hexane/EtOAc, 98:2), to give the boronic ester 2a (215.1 mg, 0.93 mmol, 93%) as a colourless oil. |
| 92% | With sodium triethylborohydride; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; toluene at 100℃; for 24h; Microwave irradiation; Inert atmosphere; regioselective reaction; | |
| 92% | With zinc trifluoromethanesulfonate; sodium triethylborohydride In tetrahydrofuran; toluene at 80℃; for 10h; Schlenk technique; Inert atmosphere; regioselective reaction; | |
| 90% | With bis(trimethylsilyl)amide yttrium(III) In toluene at 80℃; for 24h; Inert atmosphere; | 4 The preparation of (E)-2-(4-fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the structural formula is as follows: Under the protection of nitrogen, add raw material 4-fluorophenylacetylene (0.5mmol), catalyst Y[N(SiMe3)2]3 (1mol%), HBpin (1.2mmol), toluene (2mL), react at 80 for 24h, the product is separated and yielded Rate 90% |
| 89% | With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 60℃; for 24h; | |
| 89% | With Lithium 1,1,1,3,3,3-hexamethyldisilazide In toluene at 100℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique; | |
| 86% | With [FeH(tBuPNP)] In hexane at 20℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique; regioselective reaction; | |
| 86% | With tris(pentafluorophenyl)borate In toluene at 60℃; for 2h; Inert atmosphere; regioselective reaction; | |
| 84.3% | With dimethylsulfide borane complex; cyclohexene In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Schlenk technique; | |
| 84% | With tropylium tetrafluoroborate In neat (no solvent) at 70℃; for 12h; Inert atmosphere; | |
| 82% | With silver hexafluoroantimonate In neat (no solvent) at 20℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction; | |
| 82% | With silver(I) acetate In toluene at 120℃; for 18h; Schlenk technique; Inert atmosphere; stereoselective reaction; | |
| 82% | With 8C4H8O*10Br(1-)*5Co(2+)*2C14H10N8; sodium triethylborohydride In tetrahydrofuran; tert-butyl methyl ether at 45℃; for 10h; Inert atmosphere; Schlenk technique; regioselective reaction; | |
| 81% | With dibutylmagnesium In n-heptane; toluene at 80℃; for 18h; Inert atmosphere; regioselective reaction; | |
| 80% | With trimethylsilylmethyllithium In neat (no solvent) at 90℃; for 8h; Schlenk technique; Glovebox; Inert atmosphere; | |
| 78% | With bis-(phosphoranyl)methanido aluminum hydride In benzene-d6 at 110℃; for 6h; Inert atmosphere; | |
| 76% | With LDBBA In neat (no solvent) at 50℃; for 12h; Inert atmosphere; | |
| 73% | With diisobutylaluminium hydride In hexane; toluene at 110℃; for 2h; Inert atmosphere; | |
| 72% | With C27H44N3Si3V In diethyl ether at 20℃; for 16h; Inert atmosphere; regioselective reaction; | |
| 70% | With p-N,N-dimethylaminobenzoic acid In octane at 100℃; for 12h; Inert atmosphere; | |
| 69% | With C42H56AlN5 In neat (no solvent) at 60℃; for 12h; Sealed tube; chemoselective reaction; | |
| 69% | With triethylsilane; platinum(II) chloride; XPhos In tetrahydrofuran at 100℃; for 15h; Sealed tube; Inert atmosphere; stereoselective reaction; | |
| 66% | In neat (no solvent) at 110℃; for 12h; Inert atmosphere; | |
| 62% | With [Pt2Cl2{N(H)C(But)O}4] In cyclohexane at 70℃; for 14h; Inert atmosphere; | |
| 52% | With C28H40CuNO In acetonitrile at 20℃; for 4h; Schlenk technique; Inert atmosphere; | A General Protocol General procedure: To a flame dried Schlenk was added Et2CAACCuOPh (2.5 mol %) and a magnetic stir bar under an Ar atmosphere. 0.097 mL freshly distilled MeCN was added to fully dissolve catalyst and yield a 2.3 ± 0.1 M solution depending on the nature of the alkyne. Alkyne (0.56 mmol, 1 eq.) was added followed immediately by pinacolborane (0.57 mmol, 1.025 eq). The resulting solution is stirred at room temperature for 2 hours. After this time, the volatiles were evaporated under vacuum. 10 mL pentane was added to residue. This solution was passed through a pad of silica (5 cm diameter x 5 cm high) to remove insoluble components. Elution with 2 x 10 mL of pentane, followed by evaporation under vacuum yielding pure products 2a-m. |
| >99 %Spectr. | With 2Fe(1+)*9CO In toluene at 100℃; for 24h; Inert atmosphere; | |
| 67 %Spectr. | With platinum nanoparticles ligated by 1,3-bis[2,6-diisopropylphenyl]-4,5-diundecylimidazol-2-ylidene In hexane at 20℃; for 2h; Inert atmosphere; Schlenk technique; | |
| 74 %Spectr. | With MIL-53(Al) metal-organic framework-CoH In neat (no solvent) at 90℃; for 22h; | |
| Multi-step reaction with 2 steps 1.1: triethylamine; tricyclohexylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / cyclohexane / 4 h / 20 °C / Inert atmosphere; Sealed tube 1.2: 12 h / 20 °C / Inert atmosphere; Sealed tube 2.1: bis(pinacol)diborane; Xantphos; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium carbonate / di-isopropyl ether / 4 h / 70 °C / Inert atmosphere; Glovebox; Sealed tube | ||
| 80 %Spectr. | With 1,1'-dilithioferrocene N,N,N'N'-tetramethylethylenediamine In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; | |
| 77 %Spectr. | With C43H65MgNOP2 In neat (no solvent) at 80℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction; | |
| With C36H72B3P7Si3 In benzene-d6 at 50℃; Schlenk technique; Inert atmosphere; Glovebox; | ||
| 66 % | With potassium <i>tert</i>-butylate In neat (no solvent) at 25℃; Inert atmosphere; Glovebox; Schlenk technique; | |
| 99 %Spectr. | With C54H65AlN3P2(1+)*C24BF20(1-) In benzene at 60℃; Glovebox; Schlenk technique; | |
| 88 % | With tris(2,3,4-trifluorophenyl)borate at 80℃; Sealed tube; Glovebox; Inert atmosphere; | |
| 88 % | With C31H50NO2Si2Y In toluene at 110℃; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction; | |
| 86 % | With [Mn(2,6-bis(diisopropylphosphinomethyl)pyridine)Cl2]10 In tetrahydrofuran at 30℃; | |
| 87 % | With manganese(II) bromide; sodium triethylborohydride In hexane at 70℃; Inert atmosphere; Sealed tube; chemoselective reaction; | |
| 93 % | With 3,3'-bis[(diphenylphosphino)methyl]-2,2'-bipyridine; cobalt(II) aceylacetonate In ethyl acetate at 25℃; Schlenk technique; | |
| 90 % | With C38H30ClNOP2Pt In tetrahydrofuran at 50℃; Inert atmosphere; Schlenk technique; stereoselective reaction; | |
| 79 % | With C20H26CoIN3(1+)*I(1-) at 80℃; | |
| 97 % | With sodium triethylborohydride; C9H13Cl2CoN6 In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; | |
| With Triethoxysilane In 1,4-dioxane at 80℃; for 24h; regioselective reaction; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 84% | With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 6h; Inert atmosphere; | 4.4 Typical procedure for the Suzuki reaction of 3 and 4 General procedure: To a mixture of Pd (OAc)2 (0.025 mmol) and PPh3 (0.1 mol) in a flask under a nitrogen atmosphere, was added DMF (3.0 mL), 3 (0.75 mmol), 4 (0.5 mmol) and K2CO3 (0.5 mmol) at room temperature. After stirring at 90 °C for 6 h, the reaction mixture was diluted with EtOAc or CH2Cl2, washed with aqueous NH4Cl until neutral and brine, dried (Na2SO4), and evaporated in vacuo. The residue was chromatographed on silica gel using hexane/EtOAc (8:1-1:1) as eluent to give the corresponding products 5. All these compounds, except 5a and 5e [4], are new compounds. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 57% | With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 6h; Inert atmosphere; | 4.4 Typical procedure for the Suzuki reaction of 3 and 4 General procedure: To a mixture of Pd (OAc)2 (0.025 mmol) and PPh3 (0.1 mol) in a flask under a nitrogen atmosphere, was added DMF (3.0 mL), 3 (0.75 mmol), 4 (0.5 mmol) and K2CO3 (0.5 mmol) at room temperature. After stirring at 90 °C for 6 h, the reaction mixture was diluted with EtOAc or CH2Cl2, washed with aqueous NH4Cl until neutral and brine, dried (Na2SO4), and evaporated in vacuo. The residue was chromatographed on silica gel using hexane/EtOAc (8:1-1:1) as eluent to give the corresponding products 5. All these compounds, except 5a and 5e [4], are new compounds. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64% | With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 6h; Inert atmosphere; | 4.4 Typical procedure for the Suzuki reaction of 3 and 4 General procedure: To a mixture of Pd (OAc)2 (0.025 mmol) and PPh3 (0.1 mol) in a flask under a nitrogen atmosphere, was added DMF (3.0 mL), 3 (0.75 mmol), 4 (0.5 mmol) and K2CO3 (0.5 mmol) at room temperature. After stirring at 90 °C for 6 h, the reaction mixture was diluted with EtOAc or CH2Cl2, washed with aqueous NH4Cl until neutral and brine, dried (Na2SO4), and evaporated in vacuo. The residue was chromatographed on silica gel using hexane/EtOAc (8:1-1:1) as eluent to give the corresponding products 5. All these compounds, except 5a and 5e [4], are new compounds. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With water In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | 4.3 Typical procedure for the synthesis of 3 General procedure: To catecholborane (2.28 g, 19 mmol) in a flame-dried flask (under vacuum) under a nitrogen atmosphere, was added dropwise the terminal alkyne (18.2 mmol) at 0 °C. After stirred at 70 °C for 4-5 h, the reaction mixture was added dropwise with the solution of pinacol (4.73 g, 40 mmol) in THF (20 mL) at 0 °C, and then stirred for 12 h at room temperature. After concentrated in vacuo, the residue was diluted with hexane and washed with water and brine, dried (Na2SO4), and evaporated in vacuo to provide slightly yellow oil. The products obtained were pure enough for the subsequent step. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99% | With 2.9 weight% Cu(II) loaded porous coordination network-222 nanoparticles In ethanol; water at 80℃; Sealed tube; regioselective reaction; | 4.2. Catalytic performance test of PCN-222(Cu) with different particlesizes General procedure: Taking the synthesis of 2a for example: PCN-222(Cu, 1200 nm)(1.5 mol%) was used as catalyst, 4-methylphenylacetylene 1a(22 lL, 0.2 mmol) and B2pin2 (76 mg, 0.4 mmol) were dispersed in solvent (1 mL, VEtOH : VH2O = 3 : 7) in a sealed tube, which were kept in 80 °C for 5 h. The conversion was determined by GC-MS.After the reaction was finished, the reaction mixture was cooled to room temperature and concentrated in vacuum. Purification of the crude product with flash column chromatography (silica gel;Petroleum ether:EtOAc = 100:1-50:1) gave product 2a. |
| 95% | With copper(I) oxide; triphenylphosphine In 1,4-dioxane at 60℃; for 5h; | |
| 92% | With ethanol; sodium methylate at 22℃; for 8h; regioselective reaction; |
| 90% | With potassium methanolate In acetonitrile at 20℃; for 2h; Inert atmosphere; | |
| 89% | Stage #1: bis(pinacol)diborane With DPEPhos; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 25℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: 1-ethynyl-4-fluorobenzene In tetrahydrofuran; methanol at 25℃; Schlenk technique; Inert atmosphere; Sealed tube; | |
| 86% | With potassium carbonate; 6Cu(1+)*3C20H14N6O4(2-) In water; acetonitrile at 25℃; for 0.333333h; stereoselective reaction; | |
| 86% | With water; potassium carbonate; 6Cu(1+)*3C20H14N6O4(2-) In acetonitrile at 25℃; for 0.333333h; stereoselective reaction; | |
| 86% | With C42H65CuN3PSi In methanol; acetonitrile at 20℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction; | |
| 84% | With methanol; potassium <i>tert</i>-butylate; [CuI(4,7-di(1H-imidazole-1-yl)benzo[c][1,2,5]thiadiazole)]n at 25℃; for 1h; Schlenk technique; | |
| 82% | With triphenylphosphine In ethanol at 50℃; for 2h; | |
| 80% | With tetrabutylammonium tetrafluoroborate In methanol at 20℃; Electrochemical reaction; | |
| 80% | With tetrabutylammonium tetrafluoroborate In methanol | |
| 77% | With sodium methylate; Copper In ethanol at 25℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction; | |
| 76% | With sodium methylate; Cu(2+)*4Cu(1+)*4I(1-)*2C5H3N2O2(1-)*C5H5N*C2H7N*3C3H7NO In ethanol at 25℃; for 1h; Inert atmosphere; | 2.3. Typical procedure for the hydroborylation of alkynes General procedure: The typical experimental procedure for the hydroborylation ofalkynes is as follows: a mixture of alkyne (2 mmol), compound 1(0.006 mmol), bis(pinacolato)diboron (2.5 mmol), NaOMe(0.2 mmol) and 5 mL EtOH were successively added into a reaction flask equipped with a Ar (99.99%) balloon. Then the flask was vacuumedand charged in Ar three times to exclude air in the reactionsystem. Subsequently, the obtained reaction mixture was magneticallystirred at 25 °C for 1 h. After the reaction was completed, thecatalysts were separated by filtration and the yield was determinedby GC analysis. The pure products were obtained by columnchromatography on silica gel (petroleum ether/ethyl acetate as aneluent). |
| 69% | With [Cu(phen)(xantphosTEPD)]PF6; potassium carbonate In water; acetonitrile at 20℃; for 7h; Sealed tube; Inert atmosphere; Irradiation; diastereoselective reaction; | |
| 64% | With water In toluene at 80℃; for 10h; Schlenk technique; Sealed tube; regioselective reaction; | |
| 56% | With sodium t-butanolate In methanol at 50℃; for 20h; | |
| Stage #1: bis(pinacol)diborane With copper; sodium methylate In 1,4-dioxane; ethanol for 0.5h; Inert atmosphere; Sealed tube; Stage #2: 1-ethynyl-4-fluorobenzene In 1,4-dioxane; ethanol at 60℃; Inert atmosphere; | ||
| Stage #1: bis(pinacol)diborane With copper; sodium methylate In 1,4-dioxane; ethanol for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 1-ethynyl-4-fluorobenzene In 1,4-dioxane; ethanol at 60℃; for 12h; Inert atmosphere; Schlenk technique; | ||
| 93 % | With ethanol at 30℃; Autoclave; Inert atmosphere; | |
| 92 % | With cerium(IV) oxide; potassium methanolate In methanol; toluene at 50℃; Inert atmosphere; | |
| 95 % | With methanol; N-propyl-N-(2-(pyridin-2-ylamino)phenyl)formamide In tetrahydrofuran at 60℃; Schlenk technique; stereoselective reaction; | |
| With sodium methylate; Copper In ethanol at 20℃; | ||
| 70 % | With aluminum oxide; triphenylphosphine; copper(l) chloride In tetrahydrofuran; methanol at 20℃; | General procedure A General procedure: The mixture of alkyne (0.3 mmol, 1 equiv.), B2Pin2 (91.5 mg, 0.36 mmol, 1.2 equiv.), CuCl (1.5 mg,0.015 mmol, 5% mol), PPh3 (7.8 mg, 0.03 mmol, 10% mol), Al2O3 (abcr AB354683, 37.5 mg, 0.36mmol, 1.2 equiv.), and MeOH (24.3 μL, 2 equiv.) was stirred in THF (1.5 ml) at ambienttemperature for 22 h under Ar atmosphere. Then the mixture was diluted with CH2Cl2, filteredthrough celite, and the solvents were evaporated in vacuo. The crude product was purified bycolumn chromatography. |
| 71 % | With methanol; sodium t-butanolate In tetrahydrofuran at 60℃; Inert atmosphere; Schlenk technique; Glovebox; | |
| With triethylamine In ethanol at 85℃; for 0.5h; Schlenk technique; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | Stage #1: 2-[(1E)-2-(4-fluorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium hydroxide In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; | |
| 41.4 mg | Stage #1: 2-[(1E)-2-(4-fluorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium hydroxide In tetrahydrofuran; water at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; water at 20℃; for 2h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 47% | With [1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene][2-isopropoxy-5-(2,2,2-trifluoroacetamido)benzylidene]ruthenium(II) dichloride In toluene for 1h; Inert atmosphere; Reflux; stereoselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium periodate; ammonium acetate In water; acetone Inert atmosphere; | ||
| Stage #1: 2-[(1E)-2-(4-fluorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium periodate In tetrahydrofuran; water for 0.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; | ||
| Stage #1: 2-[(1E)-2-(4-fluorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium periodate In tetrahydrofuran; water at 20℃; for 0.5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 17h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91% | With copper(II) trifluoroacetate; sodium carbonate In 1,4-dioxane at 80℃; for 18h; Inert atmosphere; regioselective reaction; | General procedure for the synthesis of (E)-4,4,5,5-tetramethyl-2-styryl-1,3,2-dioxaborolane (3a) General procedure: A Schlenk tube with a magnetic stirring bar was charged with 3-phenylpropiolic acid (1a, 68 mg, 0.5 mmol), bis(pinacolato)diboron (2a, 152 mg, 0.6 mmol), Cu(TFA)2 (29 mg, 10 mol%), Na2CO3 (127 mg, 1.2 mmol), and 1,4-dioxane (2 mL) under N2. The reaction mixture was stirred at 80 °C for 18 h (monitored by TLC and GC). Upon completion of the reaction, the reaction mixture was then cooled to ambient temperature, diluted with ethyl acetate (20 mL), filtered through a plug of silica gel, and washed with ethyl acetate (20 mL). The organic layer was washed with saturated brine (20 mL×2) and dried over anhydrous Na2SO4. The solvents were removed via rotary evaporator and the residue was purified by flash chromatography (silica gel, ethyl acetate: petroleum ether=1:30) to give 89.7 mg of desired product 3a in 78 % yield as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.48-7.50 (m, 2H), 7.41 (d, 1H, J=18.5Hz), 7.29-7.32 (m, 3H), 6.18 (d, 1H, J=18.4Hz), 1.32 (s, 12H). 13C NMR (100 MHz, CDCl3): δ 148.5, 136.4, 127.9, 127.5, 126.0, 82.3, 23.8 |
| 83% | With copper(l) iodide; lithium methanolate; bis[2-(diphenylphosphino)phenyl] ether In dimethyl sulfoxide at 50℃; for 16h; | General Procedure. General procedure: Phenylpropiolic acid (439 mg, 3.0 mmol), B2pin2 (763 mg, 3.0 mmol), lithium methoxide (23 mg, 0.6 mmol), copper iodide (57 mg, 0.3 mmol), and Dpe-Phos (324 mg, 0.6 mmol) were added to a vial containing DMSO (5 mL). The suspension was stirred for 16 h at 50 °C. The reaction was monitored by TLC, and after the completion of the reaction, the reaction mass was cooled to 25-28 °C and quenched into a mixture of 50 mL of water and 50 mL of ethyl acetate. The ethyl acetate layer was washed with water (2 × 25 mL), brine (2 × 25 mL), and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography (hexane:EtOAc = 9.5:0.5). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | Stage #1: para-fluorostyrene; 2-chloro-1,3,2-benzodioxaborole With N-Methyldicyclohexylamine; (bis(3,5-di-tertbutylphenyl)(tert-butyl)phosphine)2PdCl2; lithium iodide at 70℃; for 24h; Inert atmosphere; Stage #2: 2,3-dimethyl-2,3-butane diol at 20℃; for 1h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 54% | With sodium t-butanolate In 1,4-dioxane at 120℃; for 6h; Inert atmosphere; Sealed tube; chemoselective reaction; |