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[ CAS No. 2156-04-9 ] {[proInfo.proName]}

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Chemical Structure| 2156-04-9
Chemical Structure| 2156-04-9
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Product Details of [ 2156-04-9 ]

CAS No. :2156-04-9 MDL No. :MFCD00239441
Formula : C8H9BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QWMJEUJXWVZSAG-UHFFFAOYSA-N
M.W : 147.97 Pubchem ID :2734393
Synonyms :

Calculated chemistry of [ 2156-04-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.36
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : -0.1
Log Po/w (MLOGP) : 0.85
Log Po/w (SILICOS-IT) : 0.01
Consensus Log Po/w : 0.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.04
Solubility : 1.36 mg/ml ; 0.00918 mol/l
Class : Soluble
Log S (Ali) : -2.06
Solubility : 1.29 mg/ml ; 0.00869 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.71
Solubility : 2.86 mg/ml ; 0.0193 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 2156-04-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2156-04-9 ]

* 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 [ 2156-04-9 ]

[ 2156-04-9 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 18289-89-9 ]
  • [ 2156-04-9 ]
  • [ 55032-29-6 ]
  • 3
  • [ 33065-61-1 ]
  • [ 2156-04-9 ]
  • 6-(4'-vinylphenyl)-1H-indene [ No CAS ]
  • 4
  • [ 2156-04-9 ]
  • [ 779341-90-1 ]
  • [ 854371-98-5 ]
YieldReaction ConditionsOperation in experiment
15.2% Step 7A: <strong>[2156-04-9]4-Vinylphenylboronic acid</strong> (1.89 g, 12.7 mmol, 1 equiv.) and 2-(4-Bromo-benzenesulfonylamino)-3-methyl-butyric acid tert-butyl ester (5 g, 12.7 mmol, 1 equiv.) were dissolved in ethylene glycol dimethyl ether (180 mL) and added with Pd(Ph3)4 (736.0 mg, 0.64 mmol) and stirred at room temperature for 20 min. Then to the reaction mixture was introduced an aqueous solution of K2CO3 (3.52 g, 25.5 mmol, 2 equiv.) and heat to reflux overnight. After cool to room temperature, solvent was evaporated and the residue partitioned between EtOAC and H2O. Organic layer washed with brine, dried over MgSO4, and purified by column chromatography (Silica gel, 10% EtOAc/Hexane) to yield 808 mg of G9058-169 in 15.2% yield. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.80 (d, J=6.82 Hz, 3 H) 0.95 (d, J=6.82 Hz, 3 H) 1.12 (s, 9 H) 1.99 (m, 1 H) 3.59 (dd, J=9.85, 4.55 Hz, 1 H) 5.06 (d, J=10.11 Hz, 1 H) 5.25 (d, J=10.86 Hz, 1 H) 5.75 (d, J=16.93 Hz, 1 H) 6.70 (m, 1 H) 7.45 (m, 4 H) 7.61 (d, J=8.84 Hz, 2 H) 7.82 (d, J=8.84 Hz, 2 H)
  • 5
  • [ 2156-04-9 ]
  • [ 4433-13-0 ]
YieldReaction ConditionsOperation in experiment
93% With C54H74Cl2N4O2Pd2; In ethanol; at 22℃; for 6h; Reaction flask (10 mL) equipped with stirring bar was charged with 4-vinylphenylboronic acid (135mg, 0.91 mmol), ethanol (96%) (2 mL), [{Pd(μ-OH)Cl(IPr)}2] (510-4 g, 4.55 × 10-7 mol). Reactionmixture was stirred at 22 C for 6 h. After completion of the reaction solvent was evaporated, theresidue was dissolved in hexane (5 mL) and extracted with water (2 × 2 mL). The organic layer wasdried over magnesium sulphate, and hexane was evaporated under reduced pressure. 176 mg of 4,4'-divinylbiphenyl was obtained as a white solid. Yield = 93%. 1H NMR (403 MHz, CDCl3, ppm) δ: 7.58(d, J = 8.4 Hz, 4H), 7.49 (d, J = 8.3 Hz, 4H), 6.76 (dd, J = 17.6, 10.9 Hz, 2H), 5.80 (d, J = 18.4 Hz,2H), 5.28 (d, J = 10.9 Hz, 2H); 13C NMR (101 MHz, CDCl3, ppm) δ: 140.0, 136.6, 136.3, 127.0,126.7, 126.6, 113.9. MS (EI) m/z (%) = 206 (M+, 100), 179 (9), 153 (10), 103 (8), 27 (10).
  • 6
  • [ 5969-83-5 ]
  • [ 2156-04-9 ]
  • [ 956472-60-9 ]
YieldReaction ConditionsOperation in experiment
45% With potassium fluoride;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In 1,4-dioxane; at 80℃; for 24h;Heating / reflux; Under a nitrogen stream, 23.42 g (0.158 mol) of 4-vinyl-phenyl boronic acid, 20.0 g (0.1055 mol) of 2-(4-chloro-phenyl)pyridine, 500 of 1,4-dioxane, 27.54 g (0.474 mol, 3.3 equivalent) of fluoro-potassium, 1.69 g (0.0084 mol, 5.3 mol %) of t-butylphosphine [P(t-Bu)3)], and 2.6 g (0.0028 mol, 1.8 mol %) of palladium tris(dibenzylidene acetone) [Pd2(dba)3] were placed into a 2-neck round flask 250. After the resulting solution was heated to reflux at 80 C. for 24 hours, the reaction was terminated. The resulting mixture was filtered, the catalyst and fluoro-potassium that were black solids were removed, and then the dioxane was removed by rotary evaporation. After extraction with 300 of dichloromethane and 400 of distilled water, the residue was subjected to column chromatography using a mixed solution of hexane and ethylacetate (7:3) as a developing solvent and then recrystallized at 0 C. using ethylacetate to give the 2-(4'-vinyl-biphenyl-4-yl)pyridine. The yield was 45%. As the structural characteristics of the thus prepared 2-(4'-vinyl-biphenyl-4-yl)pyridine, the 1H-NMR spectrum is shown in FIG. 2, the UV/Vis is shown in FIG. 3, the GC-Mass is shown in FIG. 4, and the FT-IR is shown in FIG. 5. Moreover, the analysis data of the 2-(4'-vinyl-biphenyl-4-yl)pyridine is shown in the following table 1: TABLE 1 Classification Nitrogen Carbon Hydrogen Theoretical Value 5.44 88.68 5.88 Measured Value 5.37 89.86 5.49
45% With potassium fluoride;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In 1,4-dioxane; at 80℃; for 24h;Heating / reflux; Example 10: Preparation of 2-(4'-vinyl-biphenyl-4-yl)pyridine; [81] Under a nitrogen stream, 23.42 g (0.158 mol) of 4-vinyl-phenyl boronic acid, 20.0 g (0.1055 mol) of 2-(4-chloro-phenyl)pyridine, 500 D of 1,4-dioxane, 27.54 g (0.474 mol, 3.3 equivalent) of fluoro-potassium, 1.69 g (0.0084 mol, 5.3 mol%) of t- butylphosphine [P(t-Bu) )], and 2.6 g (0.0028 mol, 1.8 mol%) of palladium tris(dibenzylidene acetone) [Pd (dba) ] were placed into a 2-neck round flask 250 D. After the resulting solution was heated to reflux at 8O0C for 24 hours, the reaction was terminated. The resulting mixture was filtered, the catalyst and fluoro-potassium that were black solids were removed, and then the dioxane was removed by rotary evaporation. After extraction with 300 D of dichloromethane and 400 D of distilled water, the residue was subjected to column chromatography using a mixed solution of hexane and ethylacetate (7:3) as a developing solvent and then recrystallized at O0C using ethylacetate to give the 2-(4/-vinyl-biphenyl-4-yl)pyridine. The yield was 45%. As the structural characteristics of the thus prepared2-(4/-vinyl-biphenyl-4-yl)pyridine, the H-NMR spectrum is shown in Fig. 2, the UV/ Vis is shown in Fig. 3, the GC-Mass is shown in Fig. 4, and the FT-IR is shown in Fig. 5. Moreover, the analysis data of the 2-(4'-vinyl-biphenyl-4-yl)pyridine is shown in the following table 1 :[82] Table 1
  • 7
  • [ 944149-27-3 ]
  • [ 2156-04-9 ]
  • [ 944149-54-6 ]
  • 8
  • [ 76-09-5 ]
  • [ 2156-04-9 ]
  • [ 870004-04-9 ]
YieldReaction ConditionsOperation in experiment
100% With magnesium(II) sulfate; In tetrahydrofuran; at 20℃; for 2h; General procedure: 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane 4a. 3a (1.00 g, 6.76 mmol), pinacol (802 mg, 6.80 mmol) and two spatula tips of magnesium sulphate were combined in anhydrous THF (50 mL) and left to stir at room temperature for 2 h. The mixture was filtered and concentrated under reduced pressure to afford 1.55 g of the pure expected product as a colourless liquid in quantitative yield. 1H NMR (δ, 400.0 MHz, CDCl3) 7.76 (d, 2H, J = 8.0 Hz), 7.40 (d, 2H, J = 8.0 Hz), 6.72 (dd, 1H, J1 = 11.0 Hz and J2 = 17.6 Hz), 5.81 (d, 1H, J = 17.6 Hz), 5.29 (d, 1H, J = 11.0 Hz), 1.34 (s, 12H). 13C NMR (δ, 100.0 MHz, CDCl3) (C-B non-visible), 140.2, 136.9, 135.0 (2C), 125.5 (2C), 114.9, 83.8 (2C), 24.9 (4C). HRMS-ES (m/z) found 253.1384, calcd for [C14H19BO2Na]+ 253.1376.
96% With magnesium(II) sulfate; In dichloromethane; at 20℃; for 1h; Pinacol (3.10 g, 26.2 mmol) and MgSO4 (1.0 g) wereadded to a solution of 4-vinylphenylboronic acid (3.50 g,23.6 mmol) in 60 mL of dichloromethane at room temperature.The mixture was gently stirred for 1 h at room temperature,and MgSO4 was removed by filtration andwashed with dichloromethane. The filtrate was concentratedon a rotary evaporator and the crude product was purifiedwith flash chromatography by eluting hexane:ethyl acetate(4:1) to give colorless oil (5.23 g, 96%): 1H NMR(500 MHz, DMSO-d6) δ 7.65 (d, 2H, J = 8.7 Hz), 7.47(d, 2H, J = 8.7 Hz), 6.72-6.78 (dd, 1H, J = 18,1, 12.7 Hz),5.90 (d, 1H, J = 18.1 Hz), 5.32 (d, 1H, J = 12.7 Hz), 1.28(s, 12H).
In dichloromethane; for 3h;Molecular sieve; 4-Vinyl benzene boronic acid pinacol ester was prepared according to the literature [21,22].Specifically, a mixture of 4-vinyl phenylboronic acid (0.5 g) and pinacol (0.44 g) in 100 mL ofdichloromethane in the presence of 20 g of 4A molecular sieves was stirred at 40 C for 3 h to give a nearquantitative yield of 4-vinyl benzene boronic acid pinacol ester. Analytical data for 1H-NMR of 4-vinylbenzene boronic acid pinacol ester is given as 1H-NMR (CDCl3): δ: 1.36 (s, 12H), 5.31 (d, 1H, J = 8 Hz),5.83 (d, 1H, J = 16.0Hz), 6.7 (dd, 1H), 7.41 (d, 2H, J = 8Hz), 7.77 (d, 2H, J = 8Hz); 13C-NMR (CDCl3): δ: 140.17,136.84, 134.98, 125.46, 114.79, 114.77, 83.71, 77.00, 24.82; ESI-MS (M + H)+: m/z = 231.1. Analytical datafor 1H-NMR of the PBSCP is given as 1H-NMR (CDCl3): δ: 0.91 (m, 2H), 1.17 (dt, 9H, J = 14 Hz andJ = 6 Hz), 1.38 (s, 12H), 2.71 (m, 2H), 3.68 (dm, 6H), 7.22 (m, 2H, J = 8 Hz), 7.68 (d, 2H, J = 12 Hz);13C-NMR (CDCl3): δ: 134.93, 136.84, 129.02, 128.21, 127.35, 127.24, 83.58, 77.06, 58.82, 58.41, 29.13, 24.85,18.33, 12.44. ESI-MS (M + Na)+: m/z = 417.2.
Reference: [1]Tetrahedron Letters,2013,vol. 54,p. 1211 - 1217
[2]Angewandte Chemie - International Edition,2020,vol. 59,p. 2375 - 2379
    Angew. Chem.,2020,vol. 132,p. 2395 - 2399,5
[3]Journal of Organic Chemistry,2016,vol. 81,p. 8050 - 8060
[4]Journal of the American Chemical Society,2007,vol. 129,p. 10348 - 10349
[5]Angewandte Chemie - International Edition,2018,vol. 57,p. 9785 - 9789
    Angew. Chem.,2018,vol. 130,p. 9933 - 9937,5
[6]Organic Letters,2020,vol. 22,p. 9729 - 9734
[7]Structural Chemistry,2017,vol. 28,p. 493 - 500
[8]Organic Letters,2018,vol. 20,p. 888 - 891
[9]Angewandte Chemie - International Edition,2019,vol. 58,p. 15239 - 15243
    Angew. Chem.,2019,vol. 131,p. 15383 - 15387,5
[10]Organic and Biomolecular Chemistry,2021,vol. 19,p. 4037 - 4042
[11]Journal of the American Chemical Society,2018,vol. 140,p. 16360 - 16367
[12]Organic Letters,2020,vol. 22,p. 1222 - 1226
[13]Journal of Organic Chemistry,2021,vol. 86,p. 2929 - 2940
[14]Journal of the American Chemical Society,2021,vol. 143,p. 13022 - 13028
[15]Angewandte Chemie - International Edition,2019,vol. 58,p. 12216 - 12222
    Angew. Chem.,2019,vol. 131,p. 12344 - 12350
[16]Organic Letters,2021,vol. 23,p. 1495 - 1499
[17]Organic Letters,2020,vol. 22,p. 6288 - 6293
[18]Organic and Biomolecular Chemistry,2008,vol. 6,p. 4662 - 4667
[19]Inorganica Chimica Acta,2011,vol. 365,p. 408 - 413
[20]Organic Letters,2015,vol. 17,p. 3086 - 3089
[21]Journal of the American Chemical Society,2017,vol. 139,p. 18307 - 18312
[22]Molecules,2018,vol. 23
[23]Chemistry - A European Journal,2021,vol. 27,p. 15396 - 15405
  • 9
  • [ 849677-25-4 ]
  • [ 2156-04-9 ]
  • C34H25N [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 60℃; for 10h; Under the atmosphere of argon gas, Compound 14 (2.3 g, 5.4 mmol)4-vinylphnyl boronic acid (0.8 g, 5.4 mmol) and tetrakis(triphenylphosphino) palladium (0.19 g, 0.16 mmol) were added in dimethoxyethane (10 milliliter) and an aqueous solution (8 milliliter) of 2M sodium carbonate and then the resultant was stirred at 60C for 10 hours. After pouring water (100 milliliter) and toluene (100 milliliter) in the resultant reaction solution, an organic layer was extracted, followed by drying the organic layer with the use of magnesium sulfate anhydride. The solvent of the organic layer extracted was condensated under vacuum and then the residue obtained was refined with silica gel column chromatography (hexane/methylene chloride) and as a result, Compound 15 was obtained. Product Amount: 1.1 g, Yield: 46 %.
  • 10
  • [ 36809-26-4 ]
  • [ 2156-04-9 ]
  • [ 845754-77-0 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate; tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; water; at 80℃; for 24h; 4-Bromotriphenylamine (5.98 g, 18.4 mmol), 4-vinylphenylboronic acid (3.00 g, 20.3 mmol), and tetrakis(triphenylphosphine)palladium(0) (1.94 g) were stirred in 154 mL of THF. After adding 92.5 mL of aqueous 1 M K2CO3, the reaction mixture was reacted at 80 C for 24 h. The crude mixture was cooled to ambient temperature. The solvent was removed by evaporation under reduced pressure, and the reaction mixture was poured into water and extracted with CH2Cl2 three times.The combined organic solution was dried over anhydrous MgSO4 and filtered.After evaporation of the solvent, the residue was purified by silica column chromatography with n-hexane and CH2Cl2 (4:1) to give a white solid (5.31 g, 83%).1H NMR (400 MHz, CDCl3): δ = 5.19-5.22 (d, 1H), 5.70-5.75 (d, 1H), 6.67-6.73 (dd, 1H), 7.97-7.50 (m, 18H).13C NMR (100 MHz, CDCl3): δ = 113.54, 122.92, 123.80, 124.11, 124.40, 126.60, 127.51, 129.24, 134.48, 136.05, 136.40, 139.94, 147.19, 147.60. HRMS (m/z): calcd for C26H21N, 347.1674. Found: 347.1672.
41% Example 7; Synthesis of a monomer of:; [0062] A degassed solution of K2CO3 (8.20 g, 15.4 mmol) in H2O (100 ml_) was added to a mixture of (4-bromophenyl)diphenyl amine (5.00 g, 1.54 mmol), 4- (vinyl)phenylboronic acid (3.53 g, 18.2 mmol) and Pd(PPh3)4 (0.89 g, 0.77 mmol) in monoglyme (100 ml_) and then heated to 8OC overnight. Upon cooling, the mixture was diluted with diethylether and 1 M HCI (~10mL) was added. After neutralization with a saturated solution of NaHCO3, the organic layer was separated and dried over MgSO4. Upon evaporation of the solvent a yellow solid was obtained which was purified by chromatography on silica (hexane) to obtain the desired product as a white powder (2.2 g, 41%). The product's 1H NMR is shown below.
41% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water;Heating; A degassed solution of K2CO3 (8.20 g, 15.4 mmol) in H2O (100 mL) was added to a mixture of (4-bromophenyl)diphenyl amine (5.00 g, 1.54 mmol), 4-(vinyl)phenylboronic acid (3.53 g, 18.2 mmol) and Pd(PPh3)4 (0.89 g, 0.77 mmol) in monoglyme (100 mL) and then heated to 8 C. overnight. Upon cooling, the mixture was diluted with diethylether and 1 M HCl(10 mL) was added. After neutralization with a saturated solution of NaHCO3, the organic layer was separated and dried over MgSO4. Upon evaporation of the solvent a yellow solid was obtained which was purified by chromatography on silica (hexane) to obtain the desired product as a white powder (2.2 g, 41%). See FIG. 4.
8.4 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 85℃; for 5h;Inert atmosphere; A four-neck flask was charged under argon atmosphereN-4-bromophenyl-N, N-diphenylamine(45.40 g), 4-vinylphenylboronic acid (24.80 g),Tetrakis (triphenylphosphine) palladium(3.23 g), potassium carbonate (38.70 g), DME (560 mL) and water (15.5 mL)And heated.After cooling to room temperature (25 C), the insoluble material was filtered through celite. From the filtrate,Was distilled off under reduced pressure, and the residue was purified by column chromatography and recrystallization to obtain monomer A201 (8.40 g)

  • 11
  • [ 2156-04-9 ]
  • [ 3319-99-1 ]
  • [ 1000851-41-1 ]
  • 12
  • [ 523-27-3 ]
  • [ 2156-04-9 ]
  • [ 54842-92-1 ]
YieldReaction ConditionsOperation in experiment
With Pd(PCy3)2(dba); potassium carbonate; In ethanol; toluene; at 80 - 85℃;Inert atmosphere; General procedure: The title compounds are prepared in a manner substantially similar to the proceduredescribed in reference 12 with a slight modification. A mixture of aryl dibromide or 4-bromostyrene (3 mmol), 4-vinylphenylboronic acid (6mmol or 3 mmol), 2M aq. base solution (4 mL, K2CO3), ethanol (6 mL), toluene (0.4M solution concentration of olefin), Pd(dba)(PCy3)2 1 (0.5mol%) were placed in a two-necked glass-reactor equipped with a magnetic stirring bar and reflux condenser. The suspension was degassed andheated in an oil bath at 80oC for 16h. After the reaction was completed (monitored by TLC and GCMS), the resulting mixture was concentratedand extracted with DCM and washed with water (twice). Then, the organic layer was collected and passed through by very quick ‘flash system’(glass filter, silica gel, celite) and dried over anhydrous Na2SO4 for 6h. The excess of solvent was evaporated to dryness under vacuum. Theresulting olefins were dissolved in DCM or CHCl3 (quite good or weakly soluble), isolated and purified by repeated precipitation fromDCM/hexane system. The final products were filtered off and dried under vacuum. The isolated yields were from 76 to 99% (depending on thecombination of starting dibromoarene).
  • 13
  • [ 1005487-16-0 ]
  • [ 2156-04-9 ]
  • [ 1005487-40-0 ]
YieldReaction ConditionsOperation in experiment
59% With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In toluene; at 90℃; for 4h; (Example 62) 2-(4-Cyclopropylbenzyl)-5-hydroxymethylphenyl 7-deoxy-D-glycero-β-D-gluco-heptopyranoside (Example Compound No. 1-131); (62a) Methyl 4-(4-cyclopropylbenzyl)-3-methoxymethoxybenzoate; The compound obtained in (58a) (481 mg, 1.33 mmol) was dissolved in toluene (9.0 mL), 4-vinylphenyl boronic acid (236 mg, 1.59 mmol), potassium phosphate (338 mg, 1.59 mmol), and tetrakis triphenylphosphine palladium (154 mg, 0.13 mmol) were successively added, and the mixture was stirred under a nitrogen atmosphere at 90C for 4 h. The reaction mixture was cooled back to room temperature, followed by addition of saturated aqueous ammonium chloride, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine in this order. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography (hexane:ethyl acetate, 95:5 to 82:18, v/v) to obtain a crude product (246 mg, yield 59%).
  • 14
  • [ 488-48-2 ]
  • [ 2156-04-9 ]
  • [ 1175489-19-6 ]
YieldReaction ConditionsOperation in experiment
56% General procedure: To a mixture of 1 (0.21 g, 0.5 mmol), 2aeo (2.0 mmol), palladium catalyst [tetrakis(triphenylphosphine)] in an argon flushed pressure tubewas added THF (5 ml) and aqueous K2CO3 (2 ml, 2 M). The reaction mixture was refluxed for 12 h and was allowed to cool down to room temperature and then cold water (8 ml) was added. After stirring for additional 15 min, the mixture was extracted with dichloromethane (3 20 ml). The organic layer was washed with brine, dried over anhyd Na2SO4, filtered and concentrated in vacuo to give an inseparable 1:1 mixture of 3a-o and of the corresponding 2,3,5,6-tetraaryl-p-dihydrobenzoquinone. The mixture was treated with DDQ (0.85 mmol) in benzene (8.5 ml) and was stirred at room temperature for 3 h. The reaction mixture was filtered, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (silica gel, heptanes/EtOAc¼9:1) to give products 3a-o.
  • 15
  • [ 1003-09-4 ]
  • [ 201230-82-2 ]
  • [ 2156-04-9 ]
  • [ 40828-46-4 ]
  • [ 1348072-98-9 ]
  • 16
  • [ 2156-04-9 ]
  • [ 6974-78-3 ]
  • [ 1167987-46-3 ]
  • [ 1167987-49-6 ]
  • 17
  • [ 51839-15-7 ]
  • [ 2156-04-9 ]
  • [ 1135448-60-0 ]
  • 18
  • [ 586-77-6 ]
  • [ 2156-04-9 ]
  • N,N-dimethyl-4'-vinylbiphenyl-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With bis[1,2-bis(diphenylphosphino)ethane]palladium(0); potassium carbonate; In tetrahydrofuran; water; at 100℃; for 0.5h;Microwave irradiation; Inert atmosphere; General procedure: 3 (75 mg , 0.50 mmol), 9h (100 mg, 0.50 mmol), bis[1,2-bis(diphenylphosphino)ethane]palladium(0) (5 mg, 0.005 mmol), potassium carbonate (166 mg, 1.20 mmol), THF (5 mL) and water (5 mL) were placed in a microwave vial, purged with nitrogen, sealed and stirred under microwave irradiation (power 100 W) at 100 ºC for 30 min. The mixture was cooled to rt, diluted with EtOAc (20 mL) and filtered on Celite. The filtrate was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give 139 mg of a yellow solid. The crude product was purified by chromatography on silica gel, hexane/EtOAc 9:1, to give 70 mg of the pure expected product as a yellow solid in 63% yield (0.50 mmol scale). 1H NMR (δ, 400.0 MHz, CDCl3) 7.56-7.50 (m, 4H), 7.44 (d, 2H, J = 8.6 Hz), 6.80 (d, 2H, J = 8.6 Hz), 6.74 (dd, 1H, J1 = 17.4 Hz, J2 = 10.9 Hz), 5.75 (d, 1H, J = 17.4 Hz), 5.22 (d, 1H, J = 10.9 Hz), 3.00 (s, 6H). 13C NMR (δ, 100.0 MHz, CDCl3) 150.0, 140.6, 136.6, 135.3, 128.7, 127.5 (2C), 126.6 (2C), 126.2 (2C), 113.1, 112.8 (2C), 40.6 (2C). HRMS-ES (m/z) found 224.1433, calcd for [C16H17N + H]+ 224.1434. Elemental analysis CHN (%) found C: 83.0, H: 7.2, N: 5.4, calcd for C16H17N.0.27EtOAc C: 83.0, H: 7.8, N: 5.7.
  • 19
  • [ 2039-82-9 ]
  • [ 2156-04-9 ]
  • [ 4433-13-0 ]
YieldReaction ConditionsOperation in experiment
With Pd(PCy3)2(dba); potassium carbonate; In ethanol; toluene; at 80 - 85℃;Inert atmosphere; General procedure: The title compounds are prepared in a manner substantially similar to the proceduredescribed in reference 12 with a slight modification. A mixture of aryl dibromide or 4-bromostyrene (3 mmol), 4-vinylphenylboronic acid (6mmol or 3 mmol), 2M aq. base solution (4 mL, K2CO3), ethanol (6 mL), toluene (0.4M solution concentration of olefin), Pd(dba)(PCy3)2 1 (0.5mol%) were placed in a two-necked glass-reactor equipped with a magnetic stirring bar and reflux condenser. The suspension was degassed andheated in an oil bath at 80oC for 16h. After the reaction was completed (monitored by TLC and GCMS), the resulting mixture was concentratedand extracted with DCM and washed with water (twice). Then, the organic layer was collected and passed through by very quick ‘flash system’(glass filter, silica gel, celite) and dried over anhydrous Na2SO4 for 6h. The excess of solvent was evaporated to dryness under vacuum. Theresulting olefins were dissolved in DCM or CHCl3 (quite good or weakly soluble), isolated and purified by repeated precipitation fromDCM/hexane system. The final products were filtered off and dried under vacuum. The isolated yields were from 76 to 99% (depending on thecombination of starting dibromoarene).
  • 21
  • [ 106-38-7 ]
  • [ 2156-04-9 ]
  • [ 4040-29-3 ]
YieldReaction ConditionsOperation in experiment
89% With C23H24Cl2N4Pd; potassium hydroxide; In ethanol; at 22℃; for 24h; General procedure: Glass reactor (2 mL) equipped with a reflux condenser and magnetic stirrer was charged in air with boronic acid (2.5 10-4 mol, 1.05 equiv.) and 1 mL of ethanol (99.8%). The mixture was stirred at 22 C for 5 minutes until complete dissolution of the acid. Then aryl halide (1 equiv.), dodecane (internal standard), appropriate palladium complex and KOH (1.1 equiv.) were added. The mixture was stirred at 22 C or in reflux (in a closed system) for 24 h. The course of the reaction was monitored by gas chromatography and GC/MS. After completion of the reaction, 2 mL of water and 2 mL of hexane were added to the reaction mixture. Unless stated otherwise, product was isolated from the organic layer by column chromatography (SiO2, hexane). The reaction products were identified on the basis of their spectroscopic characteristics.
68% With potassium phosphate; In tetrahydrofuran; at 60℃; for 15h;Inert atmosphere; General procedure: To a mixture of aryl halide (0.52 mmol), arylboronic acid (0.75 mmol), potassium phosphate (1.49 mmol) and solid catalyst, 7 (1.43 mol% Pd) was charged with degassed THF (3 mL). The mixture was pumped and refilled with nitrogen three times. The resulting mixture was stirred at 60 C under argon for 15 h, and then cooled to room temperature, portioned with water (5 mL) and ethyl acetate (5 mL). The solid was filtrated, washed with water and ethyl acetate. The organic layer was separated, dried over magnesium sulfate, concentrated, and purified by silica gel column chromatography to provide biaryl compounds [30,31].
67% With bis[1,2-bis(diphenylphosphino)ethane]palladium(0); potassium carbonate; In tetrahydrofuran; water; at 100℃; for 0.5h;Microwave irradiation; Inert atmosphere; General procedure: 3 (75 mg , 0.50 mmol), 9h (100 mg, 0.50 mmol), bis[1,2-bis(diphenylphosphino)ethane]palladium(0) (5 mg, 0.005 mmol), potassium carbonate (166 mg, 1.20 mmol), THF (5 mL) and water (5 mL) were placed in a microwave vial, purged with nitrogen, sealed and stirred under microwave irradiation (power 100 W) at 100 ºC for 30 min. The mixture was cooled to rt, diluted with EtOAc (20 mL) and filtered on Celite. The filtrate was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give 139 mg of a yellow solid. The crude product was purified by chromatography on silica gel, hexane/EtOAc 9:1, to give 70 mg of the pure expected product as a yellow solid in 63% yield (0.50 mmol scale).
  • 24
  • [ 2156-04-9 ]
  • [ 1435-52-5 ]
  • [ 1228186-70-6 ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 90℃; for 8h;Inert atmosphere; General procedure: 6.6 1,4-Di(4'-vinylebutylphenyl)-2-fluorobenzene (7f): Starting with 6 (100 mg, 0.39 mmol), Cs2CO3 (263 mg, 0.81 mmol), Pd(PPh3)4 (3 mol%), 4-vinylphenylboronic acid (115 mg, 0.78 mmol) and 1,4-dioxane (4 mL), 7f was isolated as a colorless solid (53 mg, 45%). Mp stable upto 375 C. 1H NMR (300 MHz, CDCl3): δ = 5.23 (dt, J = 10.87 Hz, 2H, CH2), 5.75 (q, J = 17.7, 2H, CH2), 6.70 (q, J = 17.6 Hz, 2H, CH), 7.30-7.54 (m, 11H, ArH). 13C NMR (75.46 MHz, CDCl3): δ = 29.6 (CH3), 114.3 (CH), 126.3 (2CH), 126.8 (2CH), 127.0 (2CH), 129.0 (2CH), 129.7 (2CH), 130.8 (d, J = 3.89 Hz, C), 133.1 (C), 136.2 (C), 136.4 (C), 136.9 (C), 137.2 (t, J = 2.39 Hz, C), 153.1 (d, JCF = 237.0 Hz, CF). 19F NMR (282.4 MHz, CDCl3): d -117.50 (CF). IR (ATR, cm-1): , 2852 (m), 1740 (w), 1696 (w), 1604 (w), 1547 (w), 1486 (w), 1395 (w), 1242 (w), 1185 (w), 1134 (w), 1045 (w), 1006 (w), 893 (w), 878 (w), 814 (w), 771 (w), 700 (w), 580 (w), 548 (w). MS (EI, 70 eV): m/z (%) = 300 (100) [M]+. HRMS (EI) calcd. for C22H17F [M]+: 300.13088; found 300.13021.
  • 25
  • [ 2156-04-9 ]
  • [ 1435-52-5 ]
  • [ 1228186-76-2 ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 90℃;Inert atmosphere; General procedure: 6.19 1-Bromo-4(4'-vinylphenyl)-2-fluorobenzene (8e): Starting with 6 (100 mg, 0.39 mmol), Cs2CO3 (190 mg, 0.50 mmol), Pd(PPh3)4 (3 mol%), 4-vinylphenylboronic acid (57 mg, 0.39 mmol) and 1,4-dioxane (4 mL), 8e was isolated as a colorless solid (49 mg, 45%). Mp 338-340 C. 1H NMR (300 MHz, CDCl3): δ = 5.03 (d, J = 2.3 Hz, 1H, CH), 5.58 (d, J = 4.3 Hz, 1H, CH), 6.52 (q, J = 3.7 Hz, 1H, CH), 7.00-7.13 (m, 3H, ArH), 7.23-7.35 (m, 4H, ArH). 13C NMR (75.46 MHz, CDCl3): δ = 114.5 (CH), 114.9 (CH), 123.5 (d, J = 4.3 Hz, CH), 126.4 (CH), 126.8 (CH), 126.9 (CH), 128.9 (d, J = 3.2 Hz, CH), 133.7 (CH), 136.1 (CH), 136.3 (d, J = 19.6 Hz, C), 137.5 (C), 137.6 (d, J = 2.4 Hz, C), 142.1 (d, J = 7.4 Hz, C), 159.4 (d, JCF = 243.3 Hz, CF). 19F NMR (282.4 MHz, CDCl3): δ = -107.1 (CF). IR (ATR, cm-1): , 2852 (w), 2368 (w), 2165 (w), 2046 (w), 1977 (w), 1711 (m), 1605 (w), 1573 (w), 1521 (w), 1486 (w), 1432 (w), 1359 (m), 1301 (w), 1219 (m), 1186 (w), 1116 (w), 1090 (w), 1006 (w), 989 (w), 905 (w), 878 (w), 814 (m), 771 (w), 721 (w), 668 (w), 622 (w), 578 (w), 529 (w). MS (EI, 70 eV); m/z (%) = 278 (96) (81Br) [M]+, 276 (100), 277 (18), 196 (41), 170 (14), 158. HRMS (EI) calcd. for C14H1081BrF [M]+: 277.99240; found 277.99241.
  • 26
  • [ 2156-04-9 ]
  • [ 2628-17-3 ]
YieldReaction ConditionsOperation in experiment
95% With urea hydrogen peroxide adduct; In acetonitrile; at 27 - 29℃; for 0.75h;Green chemistry; General procedure: To a stirred solution of aryl/alkyl boronic acid (1 mmol) in methanol or acetonitrile solvent (1 ml) was added 1 equiv. of Urea-Hydrogen peroxide (UHP) (2.5 equiv for alkyl boronic acids) at room temperature and the progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with dichloromethane (DCM). The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), evaporated and subjected to silica gel column chromatography for further purification.
91% With copper(II) sulfate hydrate; potassium hydroxide; In water; at 20℃; for 24h; General procedure: A flask was charged with 3,4-dimethoxyphenylboronic acid (1.0 mmol),CuSO4*H2O (0.02 g, 0.1 mmol), CNT-Chit film (10.0 mg), KOH (0.17 g, 3.0mmol), and H2O (5.00 mL). Then, the flask was stirred at room temperature in open air for 24 hours. At the end of the reaction, the reaction mixture was filtered and washed with water. Then, the filtrate was acidified with dilute aqueous HCl and extracted with diethyl ether (3 10 mL). The organic phases were combined, and the volatile components were evaporated under reduced pressure. Purification by flash column chromatography on silica gel (70%hexanes/ 30% ethyl acetate) afforded 0.1433 g of 3,4-dimethoxyphenol (2f) in 93% isolated yield as an off-white solid
78% With copper(ll) sulfate pentahydrate; ellagic acid; In methanol; at 60℃; under 760.051 Torr; for 8h;Green chemistry; General procedure: In a typical reaction, 10 mol% CuSO4·5H2O, (0.049 g, 0.2 mmol)and 6.7 mol% EA (20 mg) were mixed in methanol followed by2 mmol of phenylboronic acid. This reaction mixture was kept ina preheated oil bath by maintaining the temperature at 60 C andstirred under atmospheric pressure. After completion of the reac-tion, modified by TLC, the mixture was washed twice with hot ethylacetate to remove the reactant and product. The hot ethyl acetatewas removed from the reaction mixture and the resulting crudeproduct was purified by a column chromatography using silicagel 260 mesh (pet ether:ethyl acetate) ratio (25:75). The recov-ered catalyst was reused for the next run. All the products werecharacterized by1H and13C NMR spectra.
58% With oxygen; triethylamine; In 2-methyltetrahydrofuran; at 20℃; under 760.051 Torr; for 48h;UV-irradiation; General procedure: [1,1'-Biphenyl] -4-phenylboronic acid (59.4mg, 0.3mmol, 1.0equiv) was added to a dried 20mL quartz test tube,Vacuum the quartz test tube while backfilling with oxygen three times.Under oxygen conditions, Et3N (62.5 L, 0.45 mmol, 1.5 equiv) and 2-methyltetrahydrofuran (4 ml) were sequentially added through a syringe.The resulting mixture was stirred for 5 minutes, then the quartz test tube was transferred to a photoreactor.The test tube was placed about 2 cm from the 15W UV lamp.The reaction mixture was stirred and illuminated for 24 h,After the specified time, the crude product was diluted with ethyl acetate, filtered through a pad of silica gel, and concentrated under reduced pressure.Flash chromatography on silica gel was then performed directly on silica gel (EtOAc / PE = 1/10) to give the desired product 1b (92% yield, white solid).
With basolite C300; dihydrogen peroxide; In acetone; at 20℃; for 0.75h; General procedure: In a typical reaction, 50 mg of catalyst was added to 3 mL of acetone containing 1 mmol of phenylboronic acid and the required amount of H2O2 as given in Table 1. This reaction mixture was stirred at room temperature for the required time as indicated in Tables 1 and 2. The reaction progress was monitored by gas chromatography and after completion of the reaction, the mixture was washed twice with acetone and filtered. Then, the solvent was removed and the product is analysed by gas chromatography for its purity and selectivity. Conversion and selectivity were determined by Agilent gas chromatography using internal standard method. 1H NMR spectra were recorded with 400 MHz using tetramethylsilane as internal standard. The same procedure is followed for the reusability experiments.

  • 27
  • [ 2156-04-9 ]
  • [ 220843-12-9 ]
  • [ 85884-56-6 ]
YieldReaction ConditionsOperation in experiment
87% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; at 80℃; for 67h;Inert atmosphere; Example 1.6.2 2-(4-tert-butylphenyl)-5-(4'-vinylbiphenyl-4-yl)-1,3,4-oxadiazole (27 [vPBD]) A mixture of 25 (16.01 g, 44.81 mmol), 4-vinylphenylboronic acid (6.745 g, 45.58 mmol), tetrakis(triphenylphosphine)palladium (2.589 g, 2.241 mmol), sodium carbonate (17.00 g, 160.4 mmol), H2O (143 mL) and THF (240 mL) was degassed with argon for about 1 h while stirring. The reaction mixture was then maintained at about 80 C. with stirring under argon for about 66 h. Upon completion, the reaction was cooled to room temperature and poured over ethylacetate (200 mL). The organic phase was then washed with saturated sodium bicarbonate, water and brine, dried over magnesium sulfate, then filtered and concentrated in vacuo. The crude product was then purified via flash chromatography (silica, 100% dichloromethane to 19:1 dichloromethane-ethyl acetate) to afford 27 (14.8 g, 87% yield) as an off-white crystalline solid. 1H NMR (400 MHz, CDCl3): δ 8.20 (d, J=8.8 Hz, 2H), 8.08 (d, J=8.8 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 7.60-7.51 (m, 4H), 6.77 (dd, J1=17.6 Hz, J2=11.0 Hz, 1H), 5.83 (d, J=18.0 Hz, 1H), 5.31 (d, J=11.4 Hz, 1H), 1.36 (s, 9H)
  • 28
  • [ 1265393-25-6 ]
  • [ 2156-04-9 ]
  • [ 1265393-76-7 ]
YieldReaction ConditionsOperation in experiment
54% With N-ethyl-N,N-diisopropylamine;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 0.5h;Sealed tube; Microwave irradiation; Methyl 2-(2-chloro-4-methyl-6-phenylpyrimidin-5-yl)pentanoate (308 mg; 0.966 mmol), trans- beta-styrylboronic acid (429 mg; 2.90 mmol) and tetrakis(triphenylphosphine) palladium(O) (1 12 mg; 0.097 mmol) were placed in a 5 mL reaction tube and dissolved in a mixture of degassed DME (3 mL) and water (1 mL). N,N-Diisopropylethylamine (0.594 mL; 3.86 mmol) was added , the tube was sealed and irradiated in a microwave oven at 1000C for 30 min. The reaction mixture was partitioned between brine and ethyl acetate, the phases were separated and the water layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (1 -10%) in heptane to give 215 mg (54%) of the title compound as a colorless oil. ESI/APCI(+): 387 (M+H); 409 (M+Na). ESI/APCI(-): 385 (M-H). 1H NMR (DMSO-d6) δ 7.89 (1 H, d); 7.73 (2H, d); 7.34-7.54 (8H, m); 7.26 (1 H, d); 3.95 (1 H, t); 3.68 (3H, s); 2.45 (3H, s); 1.99 (1 H, m); 1.57 (1 H, m); 0.94 (2H, m); 0.61 (3H, t).
  • 29
  • [ 109-04-6 ]
  • [ 2156-04-9 ]
  • [ 69135-05-3 ]
YieldReaction ConditionsOperation in experiment
83.8% In a 250 mL round bottom flask, a mixture of 4-vinylphenylboronic acid (1.31 g,8.85 mmol), K2CO3 (3.29 g, 10.12 mmol), toluene: ethanol (10:1, 22 mL), 2-bromopyridine(1 g, 6.32 mmol) stirred under N2 gas for 5 min. The catalyst tetrakis (triphenylphosphine)palladium(0) added and refluxed for 5 h at 100 C temperature. Then, it was cooledto room temperature. The reaction was quenched with the addition of water and washedwith brine solution, then extracted with ethyl acetate finally dried with anhydrous Na2SO4,(filtration over celite to remove insoluble palladium catalyst residues). The crude productwas purified by column chromatography, with Hexane: Ethyl acetate (95:5) as eluent. Acolorless oil isolated as the desired vinyl substituted phenylpyridine ligand (yield, 83.8%).1H-NMR (400 MHz, Chloroform-d) 8.72 (d, J = 4.6 Hz, 1H), 8.00 (d, J = 8.4 Hz,2H), 7.81-7.72 (m, 2H), 7.55 (d, J = 8.3 Hz, 2H), 7.25 (ddd, J = 6.0, 4.9, 2.6 Hz, 1H), 6.80(dd, J = 17.6, 10.9 Hz, 1H), 5.85 (dd, J = 17.6, 0.9 Hz, 1H), 5.33 (dd, J = 10.9, 0.9 Hz, 1H)(Figure S1).13C-NMR (101 MHz, Chloroform-d) 157.01, 149.68, 138.70, 138.20, 136.74,136.40, 127.04, 126.62, 122.09, 120.42, 114.49 (Figure S2).
75% With potassium phosphate; In ethanol; water; at 100℃; for 8h; General procedure: A dried round bottomed flask equipped with a magnetic stirring bar was charged with 10mg Polymer anchored-Pd(II) D catalyst (PS-NPPZ-Pd) (0.0045mmol/Pd), 2-halopyridine (0.5mmol), phenylboronic acid (0.6mmol) and K3PO4 (1.0mmol) were added to a reaction vessel. The mixture was stirred in 4mL of H2O: EtOH (1:1) at 100C for 8h and then cooled to room temperature. The catalyst was filtered and the filtrate was extracted with ethyl acetate (3×10mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (10:90) as eluent to give the corresponding coupled products. The products were characterized by 1H NMR, 13C NMR and HRMS analysis.
  • 30
  • [ 2156-04-9 ]
  • [ 2039-82-9 ]
YieldReaction ConditionsOperation in experiment
78% With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide; In N,N-dimethyl-formamide; at 130℃; for 20h; General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol %), 1,10-phen (7.2 mg, 20 mol %) and DMF (2 mL). The mixture was stirred at 80 or 130 C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.
  • 31
  • [ 874-17-9 ]
  • [ 2156-04-9 ]
  • [ 1281994-90-8 ]
  • 32
  • [ 2156-04-9 ]
  • [ 72678-19-4 ]
  • [ 1281994-92-0 ]
  • 33
  • [ 1334126-71-4 ]
  • [ 2156-04-9 ]
  • [ 1334127-75-1 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); sodium ethanolate; In ethanol; at 110℃; General Procedure: An urea derivative with a bromo substituent (0.15 mmol), boronic acid (0.19 mmol), sodium ethoxide (0.31 mmol) and 1 mol-% of palladium acetate or 1 mol-% of tetrakis(triphenylphosphine)palladium(0) were suspended in 1 ml dry ethanol and stirred for 0.5 - 3 h at 110 C. Afterwards the solution was filtered and the solvent evaporated. The residue was added to water and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated. The solid was recrystallised from ethanol or methanol.
  • 34
  • [ 1223104-90-2 ]
  • [ 2156-04-9 ]
  • [ 1357584-01-0 ]
YieldReaction ConditionsOperation in experiment
70% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 70℃; for 7h;Inert atmosphere; Most of Suzuki-Miyaura coupling reactions were performed on a Chemspeed Accelerator SLT100 automated synthesizer. The robot was equipped with a four-needle head and an array of 16 parallel 13 mL glass reactors along with Solid Dosing Unit (SDU) for solid additions. All reactors were connected to a Huber Unistat (heating range: -70 to 300 C) and were equipped with a coldfinger reflux condenser in which the temperature can be fixed from -5 to 40 C. The inert atmosphere in the glass reactors of the Accelerator SLT100 was obtained by flushing with nitrogen for at least 30 min. Before the beginning of the coupling experiments, the reaction vessels were heated to 70 C, evacuated for 15 min, and then filled with nitrogen. This procedure was repeated two times to perform the reactions under an inert atmosphere with 1.5 bar flowrate. Substrates and reagents were administrated using SDU unit and solvents were transferred from the stock solutions with water and dioxane into the reaction vessels. A mixture of pyrimidine 2 (or 5) (1 mmol) in a (5/1 dioxane/water mixture, 7 mL), Dichlorobis(triphenylphosphine)-palladium(II) (5 mol%), sodium carbonate (2 mmol) and boronic acid (2 equiv.) was heated at 70 C for 7 h with a 900 rpm vortex. After cooling to room temperature, MgSO4 was added. The reaction mixture was filtered through a pad of celite, washed with CH2Cl2 and concentrated under vacuum. The product was purified by silica gel chromatography using pentane/ether (9/1) as eluent.
  • 35
  • [ 1223104-93-5 ]
  • [ 2156-04-9 ]
  • [ 1357584-38-3 ]
YieldReaction ConditionsOperation in experiment
80% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 24h;Inert atmosphere; A mixture of pyrazole 7 or 9 (1.0 equiv.), Dichlorobis(triphenylphosphine)-palladium(II) (10 mol%), sodium carbonate (2.0 equiv.) and boronic acid (2.0 equiv.) in a 5:1 mixture of dioxane and water was stirred at 100 C for 24 h. After cooling to room temperature, the solution was diluted with CH2Cl2 and then dried over anhydrous MgSO4. The reaction mixture was filtered through a pad of celite and concentrated under vacuum. The product was purified by silica gel chromatography using pentane/ether (9/1) as eluent.
  • 36
  • [ 1357583-59-5 ]
  • [ 2156-04-9 ]
  • [ 1357584-23-6 ]
YieldReaction ConditionsOperation in experiment
88% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 24h;Inert atmosphere; A mixture of pyrazole 7 or 9 (1.0 equiv.), Dichlorobis(triphenylphosphine)-palladium(II) (10 mol%), sodium carbonate (2.0 equiv.) and boronic acid (2.0 equiv.) in a 5:1 mixture of dioxane and water was stirred at 100 C for 24 h. After cooling to room temperature, the solution was diluted with CH2Cl2 and then dried over anhydrous MgSO4. The reaction mixture was filtered through a pad of celite and concentrated under vacuum. The product was purified by silica gel chromatography using pentane/ether (9/1) as eluent.
  • 37
  • [ 585-79-5 ]
  • [ 2156-04-9 ]
  • [ 1345691-21-5 ]
YieldReaction ConditionsOperation in experiment
63% With bis[1,2-bis(diphenylphosphino)ethane]palladium(0); potassium carbonate; In tetrahydrofuran; water; at 100℃; for 0.5h;Microwave irradiation; Inert atmosphere; General procedure: 3 (75 mg , 0.50 mmol), 9h (100 mg, 0.50 mmol), bis[1,2-bis(diphenylphosphino)ethane]palladium(0) (5 mg, 0.005 mmol), potassium carbonate (166 mg, 1.20 mmol), THF (5 mL) and water (5 mL) were placed in a microwave vial, purged with nitrogen, sealed and stirred under microwave irradiation (power 100 W) at 100 ºC for 30 min. The mixture was cooled to rt, diluted with EtOAc (20 mL) and filtered on Celite. The filtrate was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give 139 mg of a yellow solid. The crude product was purified by chromatography on silica gel, hexane/EtOAc 9:1, to give 70 mg of the pure expected product as a yellow solid in 63% yield (0.50 mmol scale).
  • 38
  • [ 18671-97-1 ]
  • [ 2156-04-9 ]
  • [ 1391118-28-7 ]
  • 39
  • [ 1374010-88-4 ]
  • [ 2156-04-9 ]
  • [ 1374010-81-7 ]
YieldReaction ConditionsOperation in experiment
79% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of Pd(PPh3)4 (0.017 mmol, 19.3 mg), (E)-N-(2-iodovinyl)phthalimide (0.334 mmol, 100 mg), and 0.337 mmol of boronic acid (for the synthesis of compounds 2a-e and 2h-j) or boronic acid pinacol ester (for compounds 2f,g) in toluene (3.3 mL, 0.1 M) an aqueous K2CO3 (1 mmol, 0.5 mL, 2 M) and ethanol (5 mmol, 230 mg, 0.29 mL) were added. The reaction mixture was stirred at 50 C under an argon atmosphere for 24 h. The organic layer was concentrated and the crude product was preloaded onto silica. Products were purified by silica gel chromatography, eluting with EtOAc in n-hexane-0-50%.
  • 40
  • [ 1263421-51-7 ]
  • [ 2156-04-9 ]
  • [ 1382466-35-4 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; In propan-1-ol; at 120℃; for 2h; 1 -20: Preparation of N-cyclopropyl-4-{6-(4-ethenylphenyl)-8-[(2 methylpropyl)amino]imidazo[1 ,2-a]pyrazin-3-yl}benzamideA mixture of 0.5 g (1 .17 mmol) 4-{6-bromo-8-[(2-methylpropyl)amino]imidazo[1 ,2- a]pyrazin-3-yl}-N-cyclopropylbenzamide (intermediate example 6-1 ), 345 mg (4- ethenylphenyl)boronic acid, 17 mL n-propanol, 1.75 mL of an aqueous 2M potassium carbonate solution, 15 mg triphenylphosphine, and 82 mg bis(triphenylphosphine)palladium was stirred at 120 C for 2 hours. The solution was cooled, water added and extracted with dichloromethane. The organic phase was dried over sodium sulfate. After filtration and removal of solvent the residue was subjected to a column chromatography on silica gel to give 509 mg (97%) of the title compound. 1 H-NMR (CDCh): δ= 0.67 (2H), 0.92 (2H), 1.06 (3H), 1 .08 (3H), 2.09 (1 H), 2.95 (1 H), 3.58 (2H), 5.28 (1 H), 5.80 (1 H), 6.13 (1 H), 6.34 (1 H), 6.75 (1 H), 7.47 (2H), 7.59 (1 H), 7.65 (2H), 7.87 (2H), 7.92 (2H), 7.95 (1 H) ppm.
97% With potassium carbonate; triphenylphosphine; In propan-1-ol; water; at 120℃; for 2h; A mixture of 0.5 g (1.17 mmol) 4-{6-bromo-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-N-cyclopropylbenzamide (intermediate example 6-1), 345 mg (4-ethenylphenyl)boronic acid, 17 mL n-propano, 1.75 mL of an aqueous 2M potassium carbonate solution, 15 mg triphenylphosphine, and 82 mg bis(triphenylphosphine)palladium was stirred at 120 C. for 2 hours. The solution was cooled, water added and extracted with dichloromethane. The organic phase was dried over sodium sulfate. After filtration and removal of solvent the residue was subjected to a column chromatography on silica get to give 509 mg (97%) of the title compound. 1H-NMR (CDCl3): δ=0.67 (2H), 0.92 (2H), 1.06 (3H), 1.08 (3H), 2.09 (1H), 2.95 (1H), 3.58 (2H), 5.28 (1H), 5.80 (1H), 6.13 (1H), 6.34 (1H), 6.75 (1H), 7.47 (2H), 7.59 (1H), 7.65 (2H), 7.87 (2H), 7.92 (2H), 7.95 (1H) ppm.
  • 41
  • [ 2530-85-0 ]
  • [ 2156-04-9 ]
  • [ 1332623-23-0 ]
  • 42
  • [ 83011-43-2 ]
  • [ 2156-04-9 ]
  • [ 1331753-08-2 ]
  • 43
  • [ 3132-99-8 ]
  • [ 2156-04-9 ]
  • [ 84022-87-7 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 110℃; for 16h;Inert atmosphere; Darkness; Compound 1 is a known compound,3 but was prepared differently via the following procedure. To a flame-dried three-neck round bottom flask equipped with a condenser and a gas inlet was added 3-bromobenzaldehyde (1.00 g, 5.40 mmol, 1 equiv) and 4-vinylphenylboronic acid (1.20 g, 8.11 mmol, 1.5 equiv) in DMF (30 mL) under nitrogen. The reaction mixture was purged with nitrogen for 30 minutes before tetrakis(triphenylphosphine)palladium(0) (312 mg, 0.27 mmol, 0.05 equiv) and a 2M degassed aqueous solution of potassium carbonate (1.87 g, 13.5 mmol, 2.5 equiv) were added. The reaction flask was wrapped with aluminum foil and heated to 110 C for 16 hours under an atmosphere of nitrogen. The reaction was allowed to cool to room temperature, where the contents of the reaction were added to a separatory funnel along with water (300 mL). The solution was extracted with ethyl acetate (5 x 150 mL). A small volume of brine was required when a clean phase separation did not occur. The combined organic layers were dried over anhydrous sodium sulfate, gravity filtered, and concentrated under reduced pressure to give a black viscous liquid. The crude product was purified by column chromatography (silica, dichloromethane/hexane 3:2) to afford 1 (0.96 g, 85 %) as a yellow solid. mp 160-168 oC; 1H NMR (400 MHz, CDCl3) 10.09 (s, 1H), 8.11 (br, t, J = 1.71 Hz, 1H), 7.88-7.84 (m, 2H), 7.65-7.59 (m, 3H), 7.55-7.50 (m, 2H), 6.77 (dd, J = 10.9 Hz, J = 17.6 Hz, 1H), 5.83 (d, J = 17.7 Hz, 1H), 5.30 (d, J = 10.9 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 192.1, 141.4, 138.8, 137.2, 136.8, 136.1, 132.6, 129.4, 128.6, 127.7, 127.1, 126.7, 114.4; FT-IR (KBr, ν/cm-1) 3368, 3025, 2814, 2732, 1701, 1628, 1581; HRMS (EI) m/z [M]+ calcd for 208.0888, found 208.0884.
  • 44
  • [ 69518-17-8 ]
  • [ 2156-04-9 ]
  • [ 1235864-91-1 ]
YieldReaction ConditionsOperation in experiment
With tri-tert-butyl phosphine; potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 9h;Inert atmosphere; Reflux; 3. Synthesis of 4-vinylphenylphthalonitrile A mixture of 4-vinylphenylboronic acid (291 mg, 2 mmol), 4-iodophthalonitrile (500 mg, 2 mmol), tri-tert-butylphosphine (1.2 mL, 0.5M in toluene), Pd(PPh3)4 (35 mg, 0.03 mmol), K2CO3 (6 mL, 2M), and toluene (15 mL) was refluxed for 9 hours under argon. The organic layer was separated and then the aqueous layer was extracted by EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by column chromatography on silica gel eluted with EtOAc/hexane (2/1) yielded 260 mg of 4-vinylphenylphthalonitrile.
  • 45
  • [ 1403934-60-0 ]
  • [ 2156-04-9 ]
  • [ 1403934-61-1 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate; tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; water; at 80℃; for 24h; 9-Butyl-6-iodo-9H-3,9'-bicarbazole (3.00 g, 6.42 mmol), 4-vinylphenylboronic acid (1.05 g, 7.06 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.68 g) were stirred in 54 mL of THF. After adding 32 mL of aqueous 1 M K2CO3, the reaction mixture was reacted at 80 C for 24 h. The crude mixture was cooled to ambient temperature. The solvent was removed by evaporation under reduced pressure, and the reaction mixture was poured into water and extracted with CH2Cl2 three times. The combined organic solution was dried over anhydrous MgSO4 and filtered. After evaporation of the solvent, the residue was purified by silica column chromatography with n-hexane and CH2Cl2 (4:1) to give a white solid (2.51 g, 80%). 1H NMR (400 MHz, DMSO-d6): δ = 8.54 (s, 1H), 8.53 (s, 1H), 8.26-8.28 (d, 2H), 7.85-7.89 (m, 2H), 7.74-7.78 (m, 3H), 7.62-7.65 (d, 1H), 7.53-7.55 (d, 2H), 7.27-7.44 (m, 6H), 6.72-6.80 (dd, 1H), 5.83-5.88 (d, 1H), 5.24-5.27 (d, 1H), 4.51 (t, 2H), 1.83 (quint, 2H), 1.38 (sext, 2H), 0.93-0.97 (t, 3H). 13C NMR (100 MHz, CDCl3): δ = 184.68, 180.26, 178.34, 165.60, 159.47, 156.86, 143.93, 141.93, 140.91, 140.1, 139.32, 136.04, 135.06, 130.54, 127.93, 126.43, 125.90, 123.15, 122.31, 122.21, 120.24, 119.46, 109.54, 52.93, 19.93, 14.14. HRMS (m/z): calcd for C36H30N2: 490.2409. Found: 490.2422.
  • 46
  • [ 57102-42-8 ]
  • [ 2156-04-9 ]
  • [ 845755-86-4 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; water; at 80℃; for 24h; 9-(4-Bromophenyl)-9H-carbazole (2 g, 6.2 mmol), 4-vinylphenylboronic acid (1 g, 6.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.65 g) were stirred in 52 mL of THF. After adding 31 mL of aqueous 1 M K2CO3, the reaction mixture was reacted at 80 C for 24 h. The crude mixture was cooled to ambient temperature. The solvent was removed by evaporation under reduced pressure, and the reaction mixture was poured into water and extracted with CH2Cl2 three times. The combined organic solution was dried over anhydrous MgSO4 and filtered. After evaporation of the solvent, the residue was purified by silica column chromatography with n-hexane and CH2Cl2 (4:1) to give a white solid (1.61 g, 75%). 1H NMR (400 MHz, DMSO-d6): δ = 8.25-8.27 (d, 2H), 7.98-8.00 (d, 2H), 7.79-7.81 (d, 2H), 7.71-7.73 (d, 2H), 7.62-7.64 (d, 2H), 7.42-7.47 (m, 4H), 7.28-7.34 (m, 2H), 6.78-6.85 (dd, 1H), 5.91-5.95 (d, 1H), 5.31-5.34 (d, 1H). 13C NMR (100 MHz, DMSO-d6): δ = 143.80, 139.79, 138.44, 138.33, 136.32, 135.94, 127.94, 127.88, 126.58, 126.06, 123.50, 122.59, 120.36, 119.92. HRMS (m/z): calcd for C26H19N: 345.1517. Found: 345.1601.
  • 47
  • [ 1277192-89-8 ]
  • [ 2156-04-9 ]
  • [ 1277193-53-9 ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 160℃; for 0.0833333h;Microwave irradiation; Inert atmosphere; Following the general procedure described above using 4-vinylphenylboronic acid (2f) and benzoxazine 6 the title compound 7e was obtained (0.313 g, 88%) as a yellow solid after purification by flash chromatography (20% EtOAc/hexane), mp 179-182 C; Rf (10% EtOAc/petroleum ether 40-60 C) 0.38; νmax(neat) 3406, 1628, 1595, 1467, 1337, 1276, 1101 cm-1; δH (600 MHz CDCl3) 7.49-7.42 (6H, m, Ph), 7.38-7.36 (1H, m, Ph), 7.12 ( 2H, d, J 7.2 Hz, Ph), 6.79 (1H, dd, J 17.6, 10.9 Hz, CH=CH2), 5.81 (1H, d, J 17.6 Hz, CH=CH2), 5.27 (1H, d, J 10.9 Hz, CH=CH2), 5.13 (1H, d, J 8.9 Hz, CHPh), 3.64 (1H, d, J=11.8 Hz, CH2CHPh), 3.38-3.35 (1H, m, CH2CHPh), 2.24 (3H, s, Me), 1.93 (3H, s, Me), 1.84 (3H, s, Me); δC (75.5 MHz, CDCl3) 141.9, 141.7, 139.7, 136.7, 135.5, 134.3, 130.2, 128.5, 128.1, 128.0, 126.1, 126.0, 125.3, 122.2, 119.0, 113.3, 75.5, 48.4, 17.1, 14.4, 11.9; MS (EI), m/z: 355 (100, M+); HRMS (FAB+): [M]+, found 355.1920. C25H25NO requires 355.1936.
  • 48
  • [ 79-38-9 ]
  • [ 2156-04-9 ]
  • [ 4714-11-8 ]
YieldReaction ConditionsOperation in experiment
63% With [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride; cesium fluoride; In 1,4-dioxane; water; at -196 - 100℃; for 1h;Inert atmosphere; To the reaction vessel was added dichloro [1,4-bis (diphenylphosphino) butane]6.0 mg (0.01 mmol) of palladium, 148 mg (1.0 mmol) of 4-vinylphenylboronic acid and 304 mg (2.0 mmol) of cesium fluoride were added and after purging with argon, 2 mL of 1,4-dioxane, 1 mL (5.6 mmol) was added. The mixture was cooled to -196 C., 466 mg (4.0 mmol) of chlorotrifluoroethylene was added, sealed under an argon stream, heated to 100 C. and stirred for 1 hour. After the reaction, the mixture was filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography to obtain 116 mg of 4-trifluorovinyl-1-vinyl-benzene (yield 63%).
  • 49
  • [ 26137-08-6 ]
  • [ 2156-04-9 ]
  • [ 1415703-11-5 ]
YieldReaction ConditionsOperation in experiment
82% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90℃; for 4h;Inert atmosphere; General procedure: A 1,4-dioxane solution (5-6 mL) of 4, 5 or 6 (1.0 equiv., 1 mmol), corresponding boronic acid (1.2 equiv.), K3PO4 (1.5 equiv.), and Pd(PPh3)4 (5 mol%) were heated at 90 oC for 4 h. After cooling to 20 oC, a sat. aqueous solution of NH4Cl was added. The organic and aqueous layers were separated, and the latter was extracted with 15 mL of CH2Cl2 three times. The combined organic layers were dried (Na2SO4), filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography.
  • 50
  • ethyl 2‐bromo‐4,5,6,7‐tetrahydro‐1‐benzothiophene‐3‐carboxylate [ No CAS ]
  • [ 2156-04-9 ]
  • [ 1415703-19-3 ]
YieldReaction ConditionsOperation in experiment
75% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90℃; for 4h;Inert atmosphere; General procedure: A 1,4-dioxane solution (5-6 mL) of 4, 5 or 6 (1.0 equiv., 1 mmol), corresponding boronic acid (1.2 equiv.), K3PO4 (1.5 equiv.), and Pd(PPh3)4 (5 mol%) were heated at 90 oC for 4 h. After cooling to 20 oC, a sat. aqueous solution of NH4Cl was added. The organic and aqueous layers were separated, and the latter was extracted with 15 mL of CH2Cl2 three times. The combined organic layers were dried (Na2SO4), filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography.
  • 51
  • [ 4487-59-6 ]
  • [ 2156-04-9 ]
  • [ 1422173-02-1 ]
YieldReaction ConditionsOperation in experiment
67% With bis[1,2-bis(diphenylphosphino)ethane]palladium(0); potassium carbonate; In tetrahydrofuran; water; at 100℃; for 0.5h;Microwave irradiation; Inert atmosphere; General procedure: 3 (75 mg , 0.50 mmol), 9h (100 mg, 0.50 mmol), bis[1,2-bis(diphenylphosphino)ethane]palladium(0) (5 mg, 0.005 mmol), potassium carbonate (166 mg, 1.20 mmol), THF (5 mL) and water (5 mL) were placed in a microwave vial, purged with nitrogen, sealed and stirred under microwave irradiation (power 100 W) at 100 ºC for 30 min. The mixture was cooled to rt, diluted with EtOAc (20 mL) and filtered on Celite. The filtrate was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give 139 mg of a yellow solid. The crude product was purified by chromatography on silica gel, hexane/EtOAc 9:1, to give 70 mg of the pure expected product as a yellow solid in 63% yield (0.50 mmol scale).
  • 52
  • [ 121602-03-7 ]
  • [ 2156-04-9 ]
  • [ 1443044-22-1 ]
YieldReaction ConditionsOperation in experiment
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 60℃; for 24h;Schlenk technique; Inert atmosphere; 4-vinylphenylbronic acid (1.00g, 6.76mmol),Compound 1(5.15g, 13.52mmol), and (PPh3)4Pd(0) (0.78g, 0.66mmol) were added to a 100mL Schlenk flask and subjected to three vacuum/nitrogen refill cycles. THF (60mL) and a nitrogen degassed aqueous solution of 2M K2CO3(25mL) were added and stirred for 10min under nitrogen. The mixture was heated at 60C for 24h and monitored via thin layer chromatography for reaction completion. THF was removed using a rotovap and the product was extracted with dichloromethane, successively washed with water, and dried over MgSO4. Removal of the solvent afforded the crude product. The crude product was subjected to a silica gel column using a hexane/dichloromethane mixture (5:1 by volume) as eluent. A white solid ofcompound 2was isolated in 63% yield (1.72g).1H NMR (DMOS-d6)δ(ppm): 0.85-0.88 (t, 3H, -CH3), 1.26-1.31 (q, 2H, -CH2-), 1.73-1.76 (t, 2H, -CH2-), 4.40-4.43 (t,2H, -N-CH2-), 5.26-5.29 (t, 1H, -CH=CH2), 5.86-5.90 (d, 1H,-CH=CH2), 6.76-6.82 (q, 1H, -CH=CH2), 7.57-8.60 (10H, Ph-H).
  • 53
  • [ 1449377-16-5 ]
  • [ 2156-04-9 ]
  • [ 1449377-17-6 ]
YieldReaction ConditionsOperation in experiment
81% With tris-(dibenzylideneacetone)dipalladium(0); 1,6-bis(diphenylphosphino)hexane; silver carbonate; In tetrahydrofuran; at 40℃; for 24h;Sealed tube; Inert atmosphere; General procedure: Preparation of catalyst solution. In a glovebox, to a 20 mL vial charged with dpph (136.4 mg, 0.30 mmol) and Pd2dba3 (68.7 mg, 0.075 mmol) was added THF (7.5 mL). The solution was stirred at 23 C for 30 min. The freshly prepared catalyst solution was used in the following reactions: in a glovebox, to a 7 mL vial with stir bar, charged with MIDA boronate 2 (26.2 mg, 0.1 mmol) was added Ag2CO3 (110.0 mg, 0.4 mmol). Boronic acid (0.15 mmol) was added, followed by THF (0.50 mL). An aliquot of the prepared catalyst solution (0.50 mL) was added in one portion. The vial was sealed with a septum cap and removed from the glovebox. The solution was stirred at 40 C for 24 h. The reaction mixture was filtered through a pad of Celite, concentrated in vacuo, and analyzed by 1H NMR. Select samples were dry loaded onto Celite from an acetone solution, and purified via flash chromatography on silica (Et2O/MeCN 100:0/80:20) to afford the MIDA boronate 8.
  • 54
  • [ 928014-00-0 ]
  • [ 2156-04-9 ]
  • [ 1440422-60-5 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; for 48h;Reflux; A degassed three-necked flask equipped with a reflux condenser and a magneticstirrer, was charged with 6-bromo-4-phenyl-2-(pyridin-2-yl)quinolone 1 (4.00 g, 11.00mmol), (4-vinylphenyl)boronic acid 2 (4.50 g, 22.00 mmol) and Pd(PPh3)4 (0.63 g,0.55 mmol). Then, degassed toluene (200 mL) and a degassed 2 M aqueous solutionof Na2CO3 (50 mL) were added. The reaction was heated to reflux and left stirring vigorously for 48 h. After cooling to room temperature, the resulting mixture wasfiltered and the organic layer was separated, washed with H2O (3 x 50 mL), andevaporated under reduced pressure. The obtained solid was suspended in methanol andfiltered to afford a pale white solid. Drying under vacuum resulted in the final product(3.40 g, 80%). All data matched literature data.
  • 55
  • [ 344-03-6 ]
  • [ 2156-04-9 ]
  • 1,4-bis[(4-vinylphenyl)-2,3,5,6-tetrafluoro]benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Pd(PCy3)2(dba); potassium carbonate; In ethanol; toluene; at 80 - 85℃;Inert atmosphere; General procedure: The title compounds are prepared in a manner substantially similar to the proceduredescribed in reference 12 with a slight modification. A mixture of aryl dibromide or 4-bromostyrene (3 mmol), 4-vinylphenylboronic acid (6mmol or 3 mmol), 2M aq. base solution (4 mL, K2CO3), ethanol (6 mL), toluene (0.4M solution concentration of olefin), Pd(dba)(PCy3)2 1 (0.5molpercent) were placed in a two-necked glass-reactor equipped with a magnetic stirring bar and reflux condenser. The suspension was degassed andheated in an oil bath at 80oC for 16h. After the reaction was completed (monitored by TLC and GCMS), the resulting mixture was concentratedand extracted with DCM and washed with water (twice). Then, the organic layer was collected and passed through by very quick ?flash system?(glass filter, silica gel, celite) and dried over anhydrous Na2SO4 for 6h. The excess of solvent was evaporated to dryness under vacuum. Theresulting olefins were dissolved in DCM or CHCl3 (quite good or weakly soluble), isolated and purified by repeated precipitation fromDCM/hexane system. The final products were filtered off and dried under vacuum. The isolated yields were from 76 to 99percent (depending on thecombination of starting dibromoarene).
  • 56
  • [ 1607-57-4 ]
  • [ 2156-04-9 ]
  • [ 1351272-41-7 ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 90℃; for 24h;Inert atmosphere; First of all bromotriphenylethylene (4 g, 11.94 mmol) and 4- vinylphenylboronic acid (2.12 g, 14.32 mmol) were dissolved in toluene (100 ml) into a 250 ml three neck round bottom flask. TBAB (0.32 g, 0.1 mmol) and 2M aqueous solution of K2CO3 (24 ml) were added in above solution. The mixture was stirred 0.5 h under N2 atmosphere. During the purging of N2 Pd(PPh3)4 (0.01 g, 8.65 10 3 mmol) was added into the flask. N2 purging was continued for 20 min and then mixturewas stirred at 90 C for 24 h. The product was extracted with DCM and washed with water, organic layer was dried over anhydrous magnesium sulfate. Finally, the solvent was evaporated under vacuum and the crude product was passing through the silica column using Petroleum ether-DCM (4: 1 by volume) as an eluent give TPEE (Yield 3.15 g, 88%). 1H NMR (CDCl3, ppm): 5.22 (d, 1H of CH2 group in vinyl), 5.69 (d, 1H of CH2 group in vinyl), 6.65 (dd,1H of CH group in vinyl) 6.97e7.19 (m, 19H of aromatic part) ppm.
88% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 90℃; for 24h;Inert atmosphere; The TPE was prepared by the method already reported (Scheme 2)in excellent yield [31]. The 4-vinylphenylboronic acid (2.120 g,14.32 mmol), Ph3Br (4 g, 11.94 mmol) were dissolved in toluene(100 mL) in a round bottom flask then TBAB (0.320 g, 0.1 mmol) andK2CO3 (aqueous solution, 2 M, 24 mL) were added with stirringfollowed by addition of Pd(PPh3)4 (0.010 g, 8.65 × 10-3 mmol) undernitrogen gas. The reaction lasted for 24 h at 90 C. After cooled downto room temperature, the toluene was removed via vacuum distillationand then dissolved the product in dichloromethane (DCM, 150mL). Theproduct was extracted by washing with deionized water (three times)and drying over magnesium sulfate (anhydrous). The obtainedcrude productwas further purified by from silica column chromatographyusing the mixture of DCM and petroleum ether (4: 1 v/v) andTPE was obtained with excellent yield (88%) after the solvent wasevaporated. The 1H NMR of TPE is given in supporting information(Fig. S4).
  • 57
  • [ 344-03-6 ]
  • [ 2156-04-9 ]
  • [ 1606988-74-2 ]
  • 58
  • [ 2156-04-9 ]
  • [ 488721-01-3 ]
  • (3S)-6,7-dimethoxy-3-((5R)-4-methoxy-6-methyl-9-(4-vinylphenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; toluene; at 120℃; for 48h; To a solution of 9-bromonoscapine (2.0 g, 4.1 mmol) in ethanol/toluene (1:1, v/v, 100 mL), Pd(PPh3)4 (0.59 g, 0.49 mmol),NaHCO3 (8.2 mmol) and 4-vinylphenyl boronic acid (1.25 g,8.2 mmol) were added sequentially, and the contents werestirred for 48 h at 120 C. After the starting material was completelyconsumed in the reaction (judged by TLC), reactionmixture was cooled to room temperature, the solvents wereevaporated under vacuum. The crude residue was extractedinto dichloromethane (325 mL) and washed with brinesolution. The organic layer was collected and passed througha Na2SO4 bed and later removed under reduced pressure.The crude residue was chromatographed over a triethylaminesilica gel bed, using pet. ether/ethyl acetate (7:3) aseluents, to give pure compound as colourless solid. (1.32 g)Yield: 62%; m.p: 120-122 C; [a]D25 120.22 (c1, dichloromethane);1H NMR (300 MHz, CDCl3): d 7.40 (d, J8.24 Hz, 2H),7.17 (d, J8.24 Hz, 2H), 6.97 (d, J8.16 Hz, 1H), 6.74-6.66(dd, J10.81 Hz, 17.51 Hz, 1H) 6.10 (s, 1H), 5.98 (s, 1H), 5.91(s, 1H), 5.74 (d, J17.51 Hz, 1H), 5.48 (s, 1H), 5.25 (d,J10.81 Hz, 1H), 4.47 (s, 1H), 4.10 (s, 6H), 3.90 (s, 3H), 2.66-2.54 (m, 4H), 2.27-2.13 (m, 2H), 1.77-1.64 (m, 1H). 13C NMR(75 MHz, CDCl3): d 157.9, 152.2, 147.7, 146.0, 143.6, 140.9,139.6, 136.7, 133.7, 133.5, 130.7, 130.1, 126.0, 120.4, 117.8,116.1, 114.2, 100.8, 81.9, 62.3, 61.1, 59.5, 56.9, 50.8, 46.6, 27.0,23.2, 29.6. MS (ESI): m/z 538 [MNa]; HRMS (ESI): Calcd forC30H29NO7 [MNa]; 538.1841; found: 538.1848. The 1HNMR,13C-NMR and mass spectra (ESI and HR-MS) of the finalproduct, VPN are included as supporting material (S6 to S9).
60% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; toluene; at 120℃; for 48h;Inert atmosphere; General procedure: To a solution of 9-bromonoscapine (200mg, 0.41mmol) in ethanol/toluene (1:1, v/v, 10mL) was added Pd(PPh3)4 (0.049mmol), sodium bicarbonate (0.82mmol) and 4a-g (0.82mmol), under nitrogen. Reaction mixture was heated at 120C for 48h, cooled to room temperature, solvents were removed under reduced pressure, water (10mL) was added, extracted with dichloromethane (3×25mL), and combined organic portions were washed with water, dried over anhydrous sodium sulphate and concentrated. Crude product was purified over silica gel column chromatography eluted with 25% ethyl acetate in hexanes to give pure compounds 5a-g as colorless solids.
60% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; toluene; at 120℃; for 48h; General procedure: In an oven dried round bottom flask, 9-bromonoscapine (0.2 g, 0.4072 mmol) in ethanol, toluene (10 mL, v/v, 1:1), aryl boronic acids 6a-6f (Fig. 5) (0.8145 mmol), Pd(PPh3)4 (0.04886 mmol) and sodium bicarbonate (0.8145 mmol) were added and heated at 120 C for 48 h. The reaction mixture was cooled to room temperature, solvents were removed under reduced pressure, water (10 mL) was added to the crude residue, then extracted with dichloromethane (3 9 25 mL), and combined organic portion was dried over anhydrous sodium sulphate and evaporated. The crude product was purified over silica gel column chromatography (25 % EtOAc in hexanes) to give pure compounds 5a-5f as white solids.
  • 59
  • [ 504-29-0 ]
  • [ 2156-04-9 ]
  • N-(4-vinylphenyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium phosphate monohydrate; copper(II) acetate monohydrate; In dimethyl sulfoxide; at 120℃; for 24h;Sealed tube; General procedure: An oven-dried 25 mL sealed tube with stir bar was charged with arylboronic acid (1 equiv.),2-amino pyridine (1 equiv.), Cu(OAc)2·H2O (1.2 equiv.), K3PO4·H2O(2 equiv.) and 3 or 5 mL of DMSO was added and closed the sealed tube. The reactionmixture was heated at the indicated temperature for 24 h. After the reaction finished, theproduct was extracted with ethyl acetate (5 × 3 mL). The organic layers werewashed with brine, dried over Na2SO4, and evaporated toyield the crude reaction mixture. The purification was done by combi flashmachine flash chromatography on silica gel (eluent: heptanes:EtOAc = 60:40).
  • 60
  • [ 25187-00-2 ]
  • [ 2156-04-9 ]
  • phenyl[4'-vinyl-(1,1'-biphenyl)-2-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; at 80℃; for 24h;Inert atmosphere; (2) Starting material 1 (3.08 g, 10 mmol), starting material 2 (2.22 g, 15 mmol), tetrakis(triphenylphosphine)palladium (350 mg, 0.3 mmol) and sodium carbonate (3.18 g, 30 mmol) were added to the reaction flask. The gas was exchanged three times, and THF (80 mL) and H2O (20 mL) were poured under a nitrogen atmosphere, and the mixture was heated and refluxed at 80 C for 24 hours. The reaction was quenched with water, extracted with methylene chloride, concentrated and then filtered, and then rinsed with eluent ( petroleum ether: methylene chloride = 5:1) to afford intermediate 3, yield 85%.
  • 61
  • [ 13484-50-9 ]
  • [ 2156-04-9 ]
  • 2,3,5,6-tetrakis(4-vinylphenyl)pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In toluene; at 100℃; for 18h;Schlenk technique; Inert atmosphere; General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.
  • 62
  • [ 2156-04-9 ]
  • 2-((difluoromethyl)thio)isoindoline-1,3-dione [ No CAS ]
  • (difluoromethyl)(4-vinylphenyl)sulfane [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With 4,4'-bipyridine; copper(l) iodide; lithium carbonate; In diethylene glycol dimethyl ether; at 60℃; for 15h;Inert atmosphere; Sealed tube; Procedure: Under argon conditions, 0.7 mmol of 4-vinylphenylboronic acid, 0.84 mmol of reagent, 0.35 mmolLithium carbonate, 0.035 mmol of cuprous iodide, 0.035 mmol of bipyridine (bpy) were placed in a 25 mL sealed tube and then Into 5.0mL diethylene glycol dimethyl ether (diglyme), 60 C reaction for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, Add 25mL water and 50mL ether extraction, organic phase and then washed with 20mL water three times, with anhydrous sodium sulfate drying, The solvent was removed by rotary rotation and the residue was purified by flash silica gel column to obtain the corresponding product (97 mg). The isolated product was 74% The hydrogen spectrum shows a purity greater than 98%.
  • 63
  • [ 14002-33-6 ]
  • [ 2156-04-9 ]
  • 10-(4-vinylphenyl)octahydro-[1,3,2]oxazaborinino[2,3-b][1,3,2]oxazaborinin-5-ium-10-uide [ No CAS ]
  • 64
  • [ 31297-31-1 ]
  • [ 2156-04-9 ]
  • (3S)-3-(4-ethenylphenyl)-3-hydroxy-4,6-dimethyl-2,3-dihydro-1-benzofuran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With (R)-Me-BIPAM; potassium fluoride; tris(triphenylphosphine)ruthenium(II) chloride; acetonitrile; In water; toluene; at 80℃; for 18h;Inert atmosphere; General procedure: A flask was charged with RuCl2(PPh3)2 (0.01 mmol, 2 mol %) and (R,R)-Me-BIPAM (0.011 mmol, 2.2 mol %) under a nitrogen atmosphere. Next, toluene (3.0 mL) and MeCN (0.1 mmol, 20 mol %) were added to the flask and the mixture was stirred at room temperature for 30 min to prepare the catalyst. Benzofuran-2,3-dine (0.5 mmol), arylboronic acid (0.75 mmol), KF (0.5 mmol), andH2O (0.3 mL) were then added to the catalyst solution. The reaction mixture was stirredat 80 C for 18 h, at which time the crude reaction mixture was extracted using ethyl acetate, washed with saturated NH4Cl and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel(Hexane/EtOAc) to give 3-aryl-3-hydroxybenzofuran-2-one.
  • 65
  • [ 17101-78-9 ]
  • [ 2156-04-9 ]
  • 1-(1-(phenylsulfonyl)vinyl)-4-vinylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate; In toluene; at 50℃;Inert atmosphere; General procedure: A Schlenk flask was loaded with ((1-bromovinyl)sulfonyl)benzene 1a (73.8 mg, 0.3 mmol), Pd(OAc)2 (3.4 mg, 0.015 mmol), SPhos (12.3 mg, 0.03 mmol), (3,4-dimethoxyphenyl)boronic acid 2a (81.9 mg, 0.45 mmol), Cs2CO3 (195.6 mg, 0.6 mmol) and held under vacuum for 10 min and then filled with nitrogen. Then toluene (2.0 mL) was introduced and the mixture was stirred at 50 C for 15 h. After completion of the reaction, the mixture was diluted with EtOAc (15.0 mL). The catalyst and inorganic base were filtered off using a short pad of silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on a silica gel column (using petroleum ether/EtOAc (5:1, v/v) as eluent) to give yield 78.8 mg (87% yield) of 1,2-dimethoxy-4-(1-(phenylsulfonyl)vinyl)benzene 5a as a pale yellow oil.
  • 66
  • [ 2156-04-9 ]
  • [ 89-60-1 ]
  • 4-methyl-2-nitro-4'-vinyl-1,1'-biphenyl [ No CAS ]
  • 67
  • [ 2156-04-9 ]
  • [ 108-98-5 ]
  • [ 100715-86-4 ]
YieldReaction ConditionsOperation in experiment
91% With tetra(n-butyl)ammonium hydroxide; oxygen; In ethanol; water; at 25℃; for 8h;Schlenk technique; Green chemistry; General procedure: An oven-dried Schlenk tuble equipped with a magnetic stirring bar was charged with MCM-41-1,10-Phen-CuSO4 (30 mg, 0.025 mmol), arylboronic acid (0.5 mmol), and thiol (0.75 mmol) (if solid). The tube was evacuated and filled with oxygen. Then EtOH (0.5 mL) was added by a syringe under a counter flow of oxygen. After stirring for 5 min, n-Bu4NOH (40% aq) (0.5 mL) was added by a syringe under a counter flow of oxygen. Next, thiol (0.75 mmol) (if liquid) was added by a syringe under a counter flow of oxygen. The resulting reaction mixture was stirred at 25 C for 8-24 h. The reaction mixture was then diluted with EtOAc (20 mL), and filtered. The MCM-41-1,10-Phen-CuSO4 complex was washed with distilled water (2×5 mL) and EtOH (3×5 mL), and reused in the next run. The filtrate was washed with water (2×5 mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica gel.
  • 68
  • [ 1293-65-8 ]
  • [ 2156-04-9 ]
  • 1,1'-bis(4-vinylphenyl)ferrocene [ No CAS ]
  • 69
  • [ 1293-65-8 ]
  • [ 2156-04-9 ]
  • 1,1'-bis(4-vinylphenyl)ferrocene [ No CAS ]
  • C18H15BrFe [ No CAS ]
  • 70
  • [ 1293-65-8 ]
  • [ 2156-04-9 ]
  • 1-(4-vinylphenyl)ferrocene [ No CAS ]
  • 1,1'-bis(4-vinylphenyl)ferrocene [ No CAS ]
  • C18H15BrFe [ No CAS ]
  • 71
  • [ 1293-65-8 ]
  • [ 2156-04-9 ]
  • 1-(4-vinylphenyl)ferrocene [ No CAS ]
  • 1,1'-bis(4-vinylphenyl)ferrocene [ No CAS ]
  • 72
  • [ 1293-65-8 ]
  • [ 2156-04-9 ]
  • 1-(4-vinylphenyl)ferrocene [ No CAS ]
  • C18H15BrFe [ No CAS ]
  • 73
  • [ 2156-04-9 ]
  • [ 67231-69-0 ]
  • (Z)-3-phenyl-N-(4-vinylphenyl)-2H-chromen-2-imine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With oxygen; copper(II) acetate monohydrate; In ethanol; at 20℃; for 24h; General procedure: To a round bottomed flask equipped with stir bar iminochromene (a, 1 mmol), Cu(OAc)2.H2O(20 mol %) and arylboronic acid (2.07 mmol) were added. Ethanol (5 mL) was added and the reaction mixture was stirred for 24 h at room temperature. After completion of the reaction as monitored by TLC, the organic phase was concentrated under reduced pressure and the solid residue was fractioned in ethyl acetate (20 mL) and water (10 mL) thrice. The organic phase was separated and dried on anhydrous Na2SO4.The solvent was removed in vacuum and the crude residue was purified by column chromatography with ethyl acetate/petroleum ether to afford the respective N-arylated chromene
  • 74
  • [ 75-15-0 ]
  • [ 2156-04-9 ]
  • [ 109-89-7 ]
  • 4-vinylphenyl diethylcarbamodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With copper diacetate; potassium carbonate; In acetonitrile; at 60℃; for 10h; 0.5 mmol of the reaction tubes of vinyl benzene boronic acid, 1 mmol of carbon disulfide, 2.5 mmolSeoul diethylamine, 1.5 mmol of potassium carbonate, 0.5 mmol of copper acetate, 3 ml of acetonitrile, followed by stirring at 60 After 10 hours of reaction, heating was stopped and the mixture was stirred, cooled to room temperature. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure to spinThe solvent was removed, and then purified by column chromatography to give the desired product by column chromatography eluent used for the bodyVolume ratio of 20: 1 petroleum ether: ethyl acetate mixed solvent, a yield of 81%.
81% With copper diacetate; potassium carbonate; In acetonitrile; at 60℃; for 10h;Schlenk technique; General procedure: A 25 mL dried Schlenk tube was charged with boronic acid 1 (0.5 mmol), amine 2 (2.5 mmol), CS2 (1.0 mmol), Cu(OAc)2 (1.0 mmol), K2CO3 (1.5 mmol) and MeCN (4 mL) at room temperature. The reaction mixture was stirred at 60 C for 10 h under air. After the reaction was completed, the mixture was cooled to room temperature and filtered through a plug of celite. The filtrate was then concentrated in vacuo to afford the crude product, which was then subjected to chromatography on silica gel with hexanes/EtOAc (20:1) to give the desired product 3.
  • 75
  • [ 2156-04-9 ]
  • 6-bromo-2-dodecyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione [ No CAS ]
  • 4-(4-vinylphenyl)-N-dodecyl-1,8-naphthalimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; water; at 80℃; for 24h; To a degassed solution (N2) of4-bromo-N-dodecyl-1,8-naphthalimide (1) (0.5 g, 1.29 mmol) and Pd(PPh3 )2Cl2 catalyst(0.03 g, 0.04 mmol) in THF (15 mL), a solution of <strong>[2156-04-9]4-vinylbenzeneboronic acid</strong> (0.42 g, 1.68mmol) in THF (3 mL) and aqueous K2CO3 solution (1.79 g, 12.89 mmol) in water (2 mL)were added via a syringe. The reaction mixture was stirred at 80C for 24 h. After coolingdown, the product was extracted with CH2Cl2, washed with water and dried over MgSO4.The solvent was evaporated and a crude product was subjected to column chromatographyon silica gel using the mixture of ethyl acetate and hexane (1:8, V:V) as an eluent.Compound2 was obtained as white crystals, yield 79%,m.p. 124 - 125C; 1H NMR (300MHz, CDCl3, δ,ppm): 8.72 (d, 1H, J=1.1Hz,Hnaphthalene), 8.69 (d, 1H, J=1.1Hz,Hnaphthalene), 8.48 (d, 1H, J=2.1Hz,Hnaphthalene), 8.46 (d, 1H, J=2.1Hz,Hnaphthalene), 8.16 (dd, 1H, J1 =1.1Hz, J2 =8.5Hz,Hnaphthalene), 6.76 (dd, 1H, AMX system CH = CH2 proton HA), 5.81 (dd, 1H, AMX systemCH = CH2 proton HM trans JAM = 17.6 Hz and gem JMX = 10.9 Hz), 5.30 (dd, 1H, AMX systemCH = CH2 proton HX cis J = 10.9 Hz), 4.24-4.15 (m, 2H, CH2, Haliphatic), 2.03-1.95 (m,1H, CH, Haliphatic), 1.49-1.26 (m, 8H, 4 × CH2, Haliphatic), 1.02-0.89 (m, 3H, CH3, Haliphatic).13C NMR (75.4 MHz, CDCl3, δ, ppm): 163.8, 145.6, 145.3, 136.3, 132.2, 131.9, 131.6, 131.8,131.7, 131.1, 131.0, 130.9, 128.2, 127.8, 124.2, 44.5, 38.3, 31.0, 28.5, 24.1, 23.4, 13.8, 10.9. IR,(in KBr), cm-1: 3066 ν (CHar); 2960, 2923, 2876, 2857 ν (CHaliphatic); 1698 ν (C=Oimide); 1655,1589 ν (C=Car); 1524, 1506 ν (N-O); 1462; 1346, 1234 ν (C-N); 991, 911 ν (Alk. C=C); 786,763, 750 γ (CHar). MS (APCI+, 20 V), m/z: 468 ([M+H]+). Anal. Calcd. for C32H37NO2: C,82.19; H, 7.97, N, 3.00; O, 6.84%; found C 72.77, H 6.24, N 6.62%.
  • 76
  • [ 50668-21-8 ]
  • [ 2156-04-9 ]
  • 3-(4-vinylphenyl)-9-ethylcarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; benzyltrimethylammonium chloride; potassium carbonate; In water; toluene; at 110℃; for 24h;Inert atmosphere; 3-Iodo-9-ethyl-carbazole (0.5 g, 1.5 mmol) and 4-vinylphenylboronic acid (0.46 g, 1.56 mmol) were dissolved intoluene (40 mL). Aqueous K2CO3 solution (8 mL, 2 M) and benzyltrimethylammoniumchloride (BTMA, 0.005 g, 0.02 mmol) wereadded to the reaction mixture degassed by three subsequentfreeze/thaw cycles. Thereafter, tri-tert-butylphosphine ((t-Bu)3P,0.063 g, 0.31 mmol) and tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4, 0.18 g, 0.16 mmol) were added under argon. Themixture was stirred for 24 h at 110 C. After cooling, the mixturewas diluted with ethyl acetate and organic phase was washed withwater and brine. After being dried over Na2SO4 and filtered, thesolvent was removed and the residue was purified by columnchromatography using hexane/ethyl acetate (20/1) as an eluent.The target product was recrystallized from hexane. The yield ofcolourless crystals was 30% (0.15 g). Mp 107e108 C. MS (APCI,20V), m/z(%): 298 ([MH], 100). 1H NMR (400 MHz, CDCl3, d,ppm): 1.50 (t, J 7.2 Hz, 3H, CH3), 4.45 (q, J 7.2 Hz, 2H, NCH2), 5.33(d, J 10.8 Hz, 1H, CH]CH2), 5.87 (d, J 17.6 Hz, 1H, CH]CH2),6.78e6.88 (m, 1H, CH]CH2), 7.29 (dd, J1 14.6 Hz, J2 1,2 Hz, 1H,Ar), 7.23e7.58 (m, 5H, Ar), 7.72e7.79 (m, 3H, Ar), 8.18 (d, J 7.8 Hz,1H, Ar), 8.37 (s, 1H, Ar). 13C NMR (100 MHz, CDCl3, d, ppm): 14.1(CH3), 37.9 (CH2), 108.8, 108.9, 113.6, 119.0, 119.2, 120.8, 123.3, 123.7, 125.3, 126.1, 126.9, 127.5, 132.0, 136.0, 136.8, 140.6, 141.8. IR. nmax incm1 (KBr): (CeH Ar) 3046; (CeH) 2976, 2931, 2869; (C]C Ar)1597, 1478, 1470; (CeN) 1234; (CH]CH2) 1625, 1000, 903; (CeH,Ar) 846, 812,748. Elemental analysis. Calcd. for C22H19N (%): C88.85, H 6.44, N 4.71. Found (%): C 88.80, H 6.51, N 4.76.
30% With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; benzyltrimethylammonium chloride; potassium carbonate; In water; toluene; at 90℃; for 24h;Inert atmosphere; 3-(4-Vinylphenyl)-9-ethylcarbazole (M2). 3-Iodo-9-ethylcarbazole (0.5 g, 1.5 mmol) and 4-vinylphenylboronic acid (0.46 g, 1.56 mmol) were dissolved in 40 ml of toluene. 8 ml of 2M K2CO3 aqueous solution and benzyltrimethylammonium chloride (BTMA, 0.005 g, 0.02 mmol) were added to the reaction mixture degassed by three subsequent freeze/thaw cycles. Thereafter, tri-tert-butylphosphine ((t-Bu)3P, 0.063 g, 0.31 mmol) and tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4, 0.18 g, 0.16 mmol) were added under argon. The mixture was stirred for 24 h at 90 C. After cooling, the mixture was diluted with ethyl acetate and organic phase was washed with water and brine. After being dried over Na2SO4 and filtered, the solvent was removed and the residue was purified by column chromatography using hexane/ethyl acetate (20/1) as an eluent. The target product was recrystallized from hexane. The yield of white crystals was 30 % (0.15 g); mp = 107-108 C. MS (APCI+, 20V), m/z (%): 298 ([M+H]+, 100). 1H NMR (400 MHz, CDCl3, δ, ppm): 1.50 (t, J = 7.2 Hz, 3H, CH3), 4.45 (q, J = 7.2 Hz, 2H, NCH2), 5.33 (d, J = 10.8 Hz, 1H, CH=CH2), 5.87 (d, J = 17.6 Hz, 1H, CH=CH2), 6.78-6.88 (m, 1H, CH=CH2), 7.29 (dd, J1 = 14.6 Hz, J2 = 1,2 Hz, 1H, Ar), 7.23-7.58 (m, 5H, Ar), 7.72-7.79 (m, 3H, Ar), 8.18 (d, J = 7.8 Hz, 1H, Ar), 8.37 (s, 1H, Ar). 13C NMR (100 MHz, CDCl3, δ, ppm): 14.1 (CH3), 37.9 (CH2), 108.8, 108.9, 113.6, 119.0, 119.2, 120.8, 123.3, 123.7, 125.3, 126.1, 126.9, 127.5, 132.0, 136.0, 136.8, 140.6, 141.8. IR. νmax in cm-1 (KBr): (C-H Ar) 3046; (C-H) 2976, 2931, 2869; (C=C Ar) 1597, 1478, 1470; (C-N) 1234; (CH=CH2) 1625, 1000, 903; (C-H, Ar) 846, 812, 748.
  • 77
  • FeDm3(Sb(C2H5)3)2 [ No CAS ]
  • [ 2156-04-9 ]
  • C26H40BFeN6O6Sb [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With Silasorb SPH-300; In methanol; dichloromethane; at 5℃; for 8h;Inert atmosphere; Reflux; Complex FeDm3(Sb(C2H5)3)2 (1.2 g, 1.5 mmol) and Silasorb SPH-300 (1 g) were dissolved/suspended in dichloromethane - methanol 3:1 mixture (10 mL) and a solution of 4-vinylphenylboronic acid (0.218 g, 1.5 mmol) in methanol (10 mL) was added dropwise to the stirring reaction mixture at 5 C under argon. The reaction mixture was refluxed for 8 h; the reaction course was controlled by TLC (SiO2 foil; eluent: dichloromethane). Then the reaction mixture was filtered, evaporated to a small volume (approximately 5 mL) and flash-chromatographycally separated on silica gel (30-mm layer, eluent: dichloromethane). The first elute was thrown out, the second orange elute was collected and evaporated to dryness. The solid residue was washed with hexane and dried in vacuo. Yield: 0.70 g (66%). Calc. for C26H40BFeN6O6Sb: C, 43.31; H, 5.59; N, 11.66. Found (%): C, 43,46; H, 5.70; N, 11.53. MS (MALDI-TOF): m/z: 721.1 [M]+⩽ , 632.5 [M - B4-C6H4CH=CH22++2H++Na+]+, 609 [M - B4-C6H4CH=CH22++2H++3H+]+. 1H NMR (CD2Cl2, δ, ppm): 1.39 (t, 3JHH = 8.1 Hz, 9H, CH3(Et)), 1.75 (q, 3JHH = 8.1 Hz, 6H, CH2(Et)), 2.30 (s, 9H, CH3(Dm, B-capped)), 2.31 (s, 9H, CH3(Dm, Sb-capped)), 5.20 (d, 3JHH = 10.9 Hz, 1H, H' (CH2(vinyl)), 5.77 (d, 3JHH = 17.8 Hz, 1H, H" (CH2(vinyl)), 6.75 (dd, 3JHH = 17.8 Hz, 3JHH = 10.9 Hz, 1H, CH(vinyl)), 7.38 (d, 3JHH = 7.8 Hz, 2H, 3-Ph), 7.67 (d, 3JHH = 7.8 Hz, 2H, 2-Ph). 13C{1H} NMR (CD2Cl2, δ, ppm): 10.79 (s, CH3 (Et)), 13.52 (s, CH3(Dm, B-capped)), 13.54 (s, CH3(Dm, Sb-capped)), 24.43 (s, CH2 (Et)), 112.91 (s, CH2(vinyl)), 125.63 (s, 3-Ph), 132.54 (s, 3-Ph), 137.09 (s, 4-Ph), 138.10 (s, CH (vinyl)), 152.75 (s, C=N (B-capped)), 154.01 (s, C=N (Sb-capped)). IR (KBr), ν/cm-1: 907, 999, 1035, 1088, 1185 ν(N-O), 1261 m ν(B-O), 1576 m ν(C=N), 1629 ν(C=C). UV-Vis (CH2Cl2): λmax,nm (ε · 10-3, mol-1 L cm-1): 250 (34), 279 (3.3), 287 (2.7), 294 (6.2), 295 (1.8), 312 (5.3), 362 (2.0), 451 (5.7), 454 (2.2), 498 (6.8).
  • 78
  • [ 75-89-8 ]
  • [ 2156-04-9 ]
  • 1-(2,2,2-trifluoroethoxy)-4-vinylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With pyridine; copper diacetate; sodium carbonate; In 1,2-dichloro-ethane; at 20℃; for 14h;Schlenk technique; Molecular sieve; Sealed tube; General procedure: In a nitrogen-filled glove box, a 25 mL Schlenk tube equipped with a magnetic stir bar was charged with Cu(OAc)2 (9.3 mg,0.05 mmol, 0.1 equiv), aryl boronic acid 1 (0.5 mmol, 1.0 equiv),Na2CO3 (106.0 mg, 1.0 mmol, 2.0 equiv) and 4 Å MS (250.0 mg). The vessel was sealed with a septum before removing from the glovebox. The tube was evacuated and backfilled with air for 3 times.Then DCE (5.0 mL), pyridine (39.6 mg, 0.5 mmol, 1.0 equiv) and CF3CH2OH (100.0 mg, 1.0 mmol, 2.0 equiv) were added respectivelyvia syringe. The mixture was stirred vigorously under a balloon ofair at room temperature for 14 h. Then the reaction solution was vacuum-filtered over a sintered-glass funnel with a tightly packedpad of Celite (1 cm thick), and the filter cake was rinsed with DCM(20 mL). The combined filtrates were concentrated. The residue was purified with silica gel column chromatography to provide the desired product.
  • 80
  • [ 16532-79-9 ]
  • [ 2156-04-9 ]
  • 2-[4-vinyl(1,1'-biphenyl)-4'-yl]-acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 20 - 90℃; for 24.5h;Inert atmosphere; 2-(4-Bromophenyl)acetonitrile (0.5562 g, 2.84 mmol), 4-vinylphenylboronic acid (0.4469 g,3.02 mmol) and palladium-tetrakis(triphenylphosphine) (0.045 g, 0.0389 mmol) were dissolvedin a mixture of toluene (20 mL), Aliquat 336 (0.16 g, 0.5 mmol) and 2 M aqueous potassium carbonate solution (10 mL). The mixture was stirred at room temperature for 30 min under N2 gas and then heated to 90 C for 24 h. After that the mixture was poured into water and extractedthree times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate.The crude product was purified through column chromatography on silica gel using petroleumether/chloroform (3:7) as eluent to a solid white powder. 0.404 g of CBF was recovered (65%yield). FT-IR (KBr, cm1): 2908, 2862, 2250, 1600, 1498, 900, 800. 1H-NMR (CDCl3): (ppm)7.61 (d, J = 7.5 Hz, 2H), 7.57 (d, J = 7.5 Hz, 2H), 7.44 (d, J = 6.9 Hz 2H), 6.78 (dd, J = 7.9, 2.1 Hz,1H), 5.85 (d, J = 16 Hz, 1H), 5.33 (d, J = 10 Hz, 1H), 3.82 (s, 2H). 13C-NMR (CDCl3): (ppm) =140.6 ((-CH-(CH=)C-C(=CH)-CH)), 139.6 ((-CH-(CH=)C-C(=CH)-CH)),), 137.1 ((-CH-(CH=)C-CH),136.3 ((-CH-(CH=)-C-CH=CH2), 128.9 (-CH2-C-(=CH)-CH)), 128.4 (-CH2-C-(=CH)-CH)), 126.8(NC-CH2-C-(=CH)-CH)), 117.8 (NC-CH2-C-(=CH)-CH)), 114.2 (((-CH-(CH=)-C-CH=CH2)), 23.34NC-CH2-C-(=CH)-CH)).
  • 81
  • [ 2156-04-9 ]
  • 1,12-bis(triethyl)-2,11,13,22,23,32-hexaoxa-3,10,14,21,24,31-hexaaza-1,12-diantimonypentacyclo[11.11.11.04.9.015,20.025,30]ditriaconta-3,9,14,20,24,30-hexaene(2-)iron(2+) [ No CAS ]
  • [tris(μ-1,2-cyclohexanedione dioximato-O:O′)-4-vinylphenylborato(2-N,N′,N″,N″′, N″″,N″″′)iron(2+)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With silica gel; In methanol; dichloromethane; at 5 - 40℃; for 8h;Inert atmosphere; Reflux; Complex FeNx3(Sb(C2H5)3)2 (1.2 g, 0.013 mol) and Silasorb SPH-300 (1 g) were dissolved/suspendedin a dichloromethane - methanol 3: 1 mixture (10 mL). The reaction mixture wascooled to 5 C and a solution of 4-vinylphenylboronic acid (0.20 g, 1.3 mmol) in methanol(10 mL) was added dropwise to the stirring reaction mixture under argon. The reaction mixturewas refluxed for 8 h; the reaction course was monitored by TLC (SiO2 foil; eluent: dichloromethane).Then the reaction mixture was filtered, the filtrate was evaporated to a small volume(approximately 5 mL) and flash-chromatographically separated on silica gel (30-mm layer,eluent: dichloromethane). The second orange elute was evaporated to dryness; the solidresidue was washed with hexane and dried in vacuo. Yield: 0.890 g (83%). Calc. forC26H33BFeN6O6: C, 52.73; H, 5.62; N, 14.19. Found (%): C, 52.62; H, 5.56; N, 14.05. MS (MALDITOF):m/z: 592 [M]+•. 1H NMR (CDCl3, δ, ppm): 1.80 (m, 12H, β-CH2), 2.92 (m, 12H, α-CH2), 5.25(dd, 2JHH = 1.1 Hz, 3JHH = 10.8 Hz, 1H, trans-CH2), 5.80 (dd, 2JHH = 1.1 Hz, 3JHH = 17.6 Hz, 1H,cis-CH2), 6.78 (dd, 3JHH = 10.8 Hz, 3JHH = 17.6 Hz, 1H, CH(vinyl)), 7.41 (d, 3JHH = 7.8 Hz, 2H, 3-Ar),7.65 (d, 3JHH = 7.8 Hz, 2H, 2-Ar). 13C{1H} NMR (CD2Cl2, δ, ppm): 21.51 (s, β-CH2), 26.42 (s, α-CH2),112.55 (s, CH2(vinyl)), 125.10 (s, 3-Ar), 131.83 (s, 2-Ar), 136.77 (s, CH(vinyl)), 137.44 (s, 4-Ar),155.14 (s, BOC=N), 155.35 (s, HOC=N). IR (KBr), ν/cm-1: 959, 1053 m, 1160 ν(N-O), 1198 m,1233 m ν(B-O), 1550, 1569 ν(C=N), 1628ν(C=C). UV-vis (CH2Cl2), λmax, nm(ε·10-3, mol-1 l cm-1):238 (30), 258 (14), 287 (4.8), 296 (1.1), 297 (8.3), 302 (0.7), 359 (1.4), 453 (4.5), 464 (10), 494 (6.7).The main synthetic conditions and results are summarized in Table 1.
  • 82
  • [ 5332-24-1 ]
  • [ 2156-04-9 ]
  • 3-(4-vinylphenyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90 - 100℃; for 8h;Inert atmosphere; General procedure: Compounds 3a-h were prepared according to the followinggeneral procedure [2,3]: To a 3-bromoquinoline (100 mg,0.48 mmol) suspension in dioxane (3.0 mL), placed in ascrew capped reaction tube, was added Pd(PPh3)4 (1.5 mol%, 2 mmol), aryl boronic acid (1.2 mmol), and K3PO4 (153mg, 1.5 mmole), and the mixture was flushed with dry nitrogengas for few minutes. The reaction mixture was thenheated at 90-100 C for 8 h. After completion of reaction, 20mL of water was added and the mixture was cooled to roomtemperature. The organic and aqueous layers were separatedand the latter was extracted three times with ethyl acetate (3 15 mL). Solvent was removed under reduced pressure by meansof rotary evaporation and the residue obtained was purifiedthrough column chromatography. Using the aforementionedprocedure, the following compounds were prepared:
  • 83
  • [ 580-22-3 ]
  • [ 2156-04-9 ]
  • 2-(4-vinyl-phenylamino) quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With pyridine; copper diacetate; In dichloromethane; at 25℃; for 18h;Molecular sieve; Inert atmosphere; General procedure: A flask is loaded with 2-amino or 3-aminoquinoline (1mmol), cupric acetate (1mmol), the corresponding arylboronic acid (2mmol) and 4A molecular sieves. The reaction mixture is diluted with dichloromethane (5.0mL) and pyridine (2 mmoL) is added. After stirring the heterogeneous reaction mixture for 18h at 25C under nitrogen atmosphere, the resulting slurry is filtered and the product is isolated from the organic filtrate by column chromatography (silica gel) employing mixtures of hexane-EtOAc as eluent (7:3-2:3). To monitor the reaction progress aliquots were withdrawn and analyzed by TLC performed on commercial 0.2mm aluminum-coated silica gel plates (F254), using EtOAc:hexane 3:2 as developing solvent and visualized by 254nm UV or immersion in an aqueous solution of (NH4)6Mo7O24·4H2O (0.04M), Ce(SO4)2 (0.003M) in concentrated H2SO4 (10%). 1H NMR and 13C NMR spectra were recorded at room temperature in CDCl3 as solvent using a Bruker AM-500 NMR instrument operating at 500.14MHz and 125.76MHz for 1H and 13C respectively. The 1H NMR spectra are referenced with respect to the residual CHCl3 proton of the solvent CDCl3 at delta = 7.26ppm. Coupling constants are reported in Hertz (Hz). 13C NMR spectra were proton decoupled and are referenced to the middle peak of the solvent CDCl3 at delta = 77.0ppm. Splitting patterns are designated as: s, singlet; d, doublet; t, triplet; q, quadruplet; qn, quintet; dd, double doublet, etc. High Resolution Mass Spectrometry was recorded with Thermo Scientific EM/DSQ II - DIP. The results were within ±0.02% of the theoretical values.
  • 84
  • [ 851786-15-7 ]
  • [ 2156-04-9 ]
  • C56H54N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 48h;Reflux; Inert atmosphere; A 250 mL round bottom flask, equipped with a reflux condenser and a magnetic stirrer,was degassed (flamed under vacuum) and filled with argon. 1.50 g (1.94 mmol) diBr-di-EH-PDI,0.661 g (4.47 mmol) 4-styryl boronic acid, 1.61 g (11.7 mmol) K2CO3 in 2 M aqueous solution, 0.0672g (0.0583 mmol) Pd(PPh3)4 and 55 mL toluene were added. The system was degassed, flushed withargon again and was heated to reflux temperature for 2 days. After the solution was filtered frompaper filter, followed by extraction of the organic layer with toluene and distilled water. The organicpart was stirred with magnesium sulfate (MgSO4), filtrated and the solvent was rotary evaporated.The obtained solid was dried under vacuum at 40 C overnight. Then the solid was dispersed inMeOH for further purification, was filtered and was washed with acetone. The solid was dried undervacuum at 40 C overnight. Yield: 1.034 g (65%). m.p. >400 C. 1H NMR (600 MHz, CDCl3): delta (ppm)= 8.60-8.59 (s, 1H) 8.59-8.58 (s, 1H) (8.16-8.09 (m, 2H) 7.87-7.81 (d, 2H), 7.69-7.64 (m,1H) 7.54-7.49 (m,6H) 7.48-7.44 (m,1H), 6.85-6.76 (q, 1H) 5.93-5.82 (d, 1H) 5.45-5.30(d, 1H) 4.2-4.0 (m, 4H) 2.02-1.89 (m,2H) 1.26-1.45 (m, 16H), 0.97-0.85 (m, 12H) 13C NMR (150 MHz, CDCl3) delta = 163.86, 163.83, 163.77, 149.2,141.4, 140.7, 137.9, 135.9, 135.23, 134.89, 132.6, 130.5, 130.2, 129.5, 129.3, 129.1, 127.9, 127.6, 122.3, 115.2,44.3, 37.9, 30.8, 28.7, 24.05, 23.03, 14.05, 10.62. Elemental analysis for C56H54N2O4 calcd. C 82.12, H6.65, N 3.42; found C 81.88, H 6.64 N 3.46.
  • 85
  • [ 29488-24-2 ]
  • [ 2156-04-9 ]
  • 2-phenyl-5-(4-vinylphenyl)thiophene [ No CAS ]
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