Name: 4363-35-3|(Z/E)-Styrylboronic acid|95%
Brand: Ambeed
SKU: A663127
Rating: 95 (32 reviews)

1
[ 4363-35-3 ]
[ 19978-41-7 ]
3-Bromo-5-((E)-styryl)-pyran-2-one [ No CAS ]

Reference： [1]Synlett,2004,p. 2197 - 2199

2
[ 4363-35-3 ]
[ 19978-41-7 ]
5-Bromo-3-((E)-styryl)-pyran-2-one [ No CAS ]

Reference： [1]Synlett,2004,p. 2197 - 2199

3
[ 866026-77-9 ]
[ 4363-35-3 ]
(E)-2-(5,5-dimethyl-2-styrylcyclopent-2-enyl)-1-phenylethanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 15598 - 15599

4
[ 485829-15-0 ]
[ 4363-35-3 ]
(E)-β-(15-vindolinyl)styrene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 7899 - 7902

5
[ 959912-60-8 ]
[ 4363-35-3 ]
5,5-dimethyl-2-(morpholin-4-yl)-3-[(E)-2-phenylvynyl]-5,6-dihydro-1-benzothiophen-7(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With potassium phosphate;palladium diacetate; 1,3-bis-(diphenylphosphino)propane; In 1,4-dioxane; at 90℃; for 36h;	EXAMPLE 144; 5,5-Dimethyl-2-(morpholin-4-yl')-3 - [(E)-2-phenylvmyl] -5 ,6-dihydro- 1 -benzothiophen-; A mixture of Example 16 (0.32 g, 0.93 mmol), styreneboronic acid (0.41 g, 2.79 mmol), palladium acetate (0.02 g, 0.08 mmol), l,3-bis(diphenylphosphino)propane (0.038 <n="120"/>g, 0.08 mmol) and K3PO4 (0.59 g, 3.30 mmol) in 1,4-dioxane (30 mL) was heated at 9O0C for 36 h. The reaction mixture was then concentrated in vacuo. Purification by column chromatography (SiO2, 0-25% EtOAc/hexanes) gave the title compound (0.02 g, 7%) as an off-white solid. deltaH (DMSO-d6) 7.61-7.40 (2H, m), 7.40-7.37 (2H, m), 7.30-7.26 (IH, m), 6.99 (2H, s), 3.83-3.73 (4H, m). 3.18-3.08 (4H, m), 2.80 (2H, s), 2.40 (2H, s), 0.96 (6H, s). MS (ES+) 368.0 (M+H)+.

Reference： [1]Patent: WO2007/141504,2007,A1 .Location in patent: Page/Page column 118-119

6
[ 25462-85-5 ]
[ 4363-35-3 ]
2-methyl-6-styryl-isonicotinic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A suspension of 2-chloro-6-methyl-isonicotinic acid (171.6 mg, [1] mmol), 2- [PHENYL-ETHENEBORONIC] acid (180.0 mg, 1.2 [MMOL),] [K2CO3] (414 mg), Pd [(DPPF) C12-] CH2Cl2 (27 mg) in [CH3CN-H20] (3: 1,10 mL) is stirred under argon at [90C] for 15 h. The solution is cooled to r. t. and aq. hydrochloric acid (2M, 1.5 mL) is added to adjust the pH at 3. The mixture is evaporated to dryness and purified by MPLC (C18, H2O-MeOH) to provide the title compound.

Reference： [1]Patent: WO2004/26836,2004,A2 .Location in patent: Page 31

7
[ 696-62-8 ]
[ 4363-35-3 ]
[ 1694-19-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate;Co0.38Fe0.57LaO3Pd0.05; In water; isopropyl alcohol; at 80℃; for 18h;Product distribution / selectivity;	2-2) Reaction between aryliodide and boronic acid The aryliodide and boronic acid shown in TABLE 6 were allowed to react with each other under the reaction conditions shown in TABLE 6, using the Pd-containing perovskite-like composite oxide produced in Example of production 1 as the catalyst for synthesis reaction. Yields in the respective reactions are shown in TABLE 6.

Reference： [1]Patent: US2005/215804,2005,A1 .Location in patent: Page/Page column 16-17

8
[ 23147-58-2 ]
[ 603965-77-1 ]
[ 4363-35-3 ]
[ 944541-49-5 ]

Yield	Reaction Conditions	Operation in experiment
61%	In ethanol; at 20℃; for 48h;	A mixture of 2-(l-piperazinyl)- 5-pyrimidinecarboxylic acid, ethyl ester (0.016 mol),(2-phenylethenyl)- boronic acid (0.016 mol) and l,4-dioxane-2,5-diol (0.016 mol) inEtOH (250 ml) was stirred for 2 days at room temperature and then the solvent wasevaporated (vac.), The residue was taken up in DCM and water and the organic layerwas separated, dried (MgSO4), filtered and the solvent was evaporated. The residue waspurified by column chromatography over silica gel (15-40/xm) (eluent: DCM/MeOH97/1). The pure fractions were evaporated, yielding 4g (61%) of intermediate 1, meltingpoint 128C.Esters, corresponding to intermediate 1, can be separated by chiral chromatography.
61%	In ethanol; at 20℃; for 48h;	a) Preparation of intermediate 1. A mixture of 2-(l-piperazinyl)- 5-pyrimidinecarboxylic acid, ethyl ester (0.0169 mol), (2-phenylethenyl)-boronic acid (0.0169 mol) and l,4-dioxane-2,5-diol (0.0169 mol) in ethanol (250 ml) was stirred for 2 days at room temperature and then the solvent was evaporated (vacuum). The residue was taken up in CH2Cl2 and H2O and the organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (15-40mum) (eluent: CH2C12/CH3OH 97/1). The pure fractions were evaporated, yielding 4g (61%) of intermediate 1 (M.P.: 128C; E-configuration).

Reference： [1]Patent: WO2006/10749,2006,A2 .Location in patent: Page/Page column 29
[2]Patent: WO2007/82874,2007,A1 .Location in patent: Page/Page column 28

9
[ 319472-83-8 ]
[ 4363-35-3 ]
[ 319472-84-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium hydroxide;Pd(PPh3)4; In methanol; ethyl acetate; toluene;	To 6-nitro-3-iodo-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazole (11.0 g, 26.1 mmol), styryl boronic acid (4.64, 31.4 mmol), and Pd(PPh3)4 (1.25 g, 1.08 mmol) under an atmosphere of argon was added toluene (192 mL), MeOH (4 mL) and 2N NaOH (aq) (32.6 mL, 65.3 mmol). The resulting heterogeneous mixture was heated to 90 C. After 8 h the reaction was diluted with EtOAc (150 mL) and water (50 mL), the phases were separated and the organic was extracted 2*50 mL EtOAc. The pooled organic phase was washed with brine (50 mL), then dried with Na2SO4, filtered and concentrated under reduced pressure. The crude reaction was purified by silica gel chromatography (1:9 EtOAc:hexane) to give 6-nitro-3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazole as a yellow solid (7.65 g, 74%): 13C NMR (75 MHz, CDCl3) delta 148.3, 145.0, 141.3, 138.1, 134.2, 130.5, 129.9, 129.8, 129.5, 128.1, 127.4, 123.2, 119.8, 117.8, 108.2,79.7,68.5, 19.2,0.0; MS (FAB) [M+Na]/z Calc'd 418, found 418. Anal. Calc'd: C, 63.77; H, 6.37; N, 10.62. Found: C, 64.04; H, 6.29; N, 10.56.

Reference： [1]Patent: US6531491,2003,B1

10
[ 909010-90-8 ]
[ 4363-35-3 ]
[ 909010-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 120℃; for 0.5h;Irradiation;	e) 7-Hydroxy-2-styryl-thieno[3,2-c]pyridine-6-carboxylic acid ethyl ester Under a nitrogen atmosphere ester 2-Bromo-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid ethyl ester (250 mg, 0.83 mmol, example 21.d), styreneboronic acid (185 mg, 1.25 mmol), cesium carbonate (675 mg, 2.08 mmol), and tetrakis(triphenylphosphine)palladium(0) (92 mg, 0.08 mmol) were suspended in 4 mL of anhydrous 1,4 dioxane. The reaction mixture was heated at 120 C. for 30 minutes in a CEM microwave reactor, cooled to room temperature, and diluted with ethyl acetate. The organic mixture was successively washed with water, saturated sodium bicarbonate, and brine solutions. The organic fractions were dried over anhydrous sodium sulfate and concentrated to a crude solid residue, which was then purified by column chromatography, eluding the desired product from silica gel with a gradient of 20-60% ethyl acetate in hexanes: 224 mg of an off-white solid. MS: (+) m/z 326.0 (M+1)

Reference： [1]Patent: US2006/199836,2006,A1 .Location in patent: Page/Page column 29

11
[ 29495-19-0 ]
[ 4363-35-3 ]
[ 1152495-30-1 ]
[ 84680-54-6 ]

Yield	Reaction Conditions	Operation in experiment
	In water	25 Example 25 Example 25 Alanine-proline (1,000 mg, 5.37 mmol), glyoxylic acid monohydrate (544 mg, 5.91 mml) and 2-phenylethenyl boronic acid (1,192 mg, 8 mmol) were vigorously stirred together in water (7 mL) for 48 hours. The precipitate was filtered, washed with acetone (2*10 mL) and dried to give a single crystalline product (1,488 mg, 80% yield, >99% de) the structure of which was confirmed with X-ray crystallography. 1H NMR (360 MHz, DCl/D2O) δ 7.10-7.25 (br, 5H), 6.92 (d, J=15.6 Hz, 1H), 5.78 (dd, J=15.6 Hz, 9.8 Hz, 1H), 4.75 (d, J=9.8 Hz, 1H), 4.15 (q, J=6.8 Hz, 1H), 3.84 (m, 1H), 3.20 (m, 2H), 1.58 (m, 2H), 1.41 (d, J=6.8 Hz, 3H), 1.01-1.35 (m, 2H). 13C NMR (90 MHz, DCl/D2O) δ 174.2, 168.7, 168.2, 142.6, 133.4, 130.4, 129.3, 127.1, 114.7, 62.3, 59.4, 54.0, 47.4, 28.0, 24.0, 15.1. HRMS-CI calcd for C18H22N2O5 (M+H+) 347.1528, found 347.1598. Anal. Calcd for C18H22N2O5: C, 62.42; H, 6.40; N, 8.09. Found: C, 62.46; H, 6.41 N, 8.02. This compound was hydrogenated in methanol with Pd/C as catalyst to give pure enalaprilat.

Reference： [1]Current Patent Assignee: UNIVERSITY OF SOUTHERN CALIFORNIA - US6232467, 2001, B1

12
[ 6310-09-4 ]
[ 4363-35-3 ]
[ 125972-78-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; In 1,4-dioxane; at 60℃; for 6h;Product distribution / selectivity;	In air, a vial was charged with complex Ih (6.8 mg, 0.01 mmol), potassium carbonate (207 mg, 1.50 mmol), the boronic acid (0.6 mmol) and the organohalide (0.5 mmol). The vial was sealed with a septum and purged with argon (3×). Dioxane (2.0 mL) was added and the contents were stirred at 60 C. for the specified period of time. The reaction was then diluted with diethyl ether (2 mL) and transferred to a round bottom flask. The reaction vial was rinsed with additional diethyl ether (2 mL) and combined with the previous dilution. Each reaction was performed in duplicate and the contents were combined, concentrated onto silica gel and purified by flash chromatography.

Reference： [1]Patent: US2007/73055,2007,A1 .Location in patent: Page/Page column 11; 16

13
5-(5-bromo-2-isobutoxyphenyl)-1H-pyrazole [ No CAS ]
[ 4363-35-3 ]
(E)-5-(2-isobutoxy-5-styrylphenyl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 110℃; for 7.5h;	Compound 80: (E)-5-(2-isobutoxy-5-styrylphenyl)-1H-pyrazole Compound 79 (507 mg, 1.72 mmol), phenylboronic acid (305 mg, 2.06 mmol), palladium tetrakistriphenylphosphine (99 mg, 0.09 mmol), cesium carbonate (2M, 5 mL) and toluene (5 mL) were stirred under nitrogen at 110 C. for 7.5 hours. After cooling, the mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organics were dried and concentrated. Chromatography (SiO2, 20 to 40% ethyl acetate:hexanes) gave the title compound. [M+H] calc'd for C21H23N2O: 319; found 319.

Reference： [1]Patent: US2007/197532,2007,A1 .Location in patent: Page/Page column 59-60

14
C₁₅H₂₁BrN₂O₂ [ No CAS ]
[ 4363-35-3 ]
[3-(styryl)-phenyl]carbamic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; at 0 - 120℃; for 0.166667h;Microwave irradiation;	3-Bromo-carbamic acid l-aza-bicyclo[2.2.2]oct-3-yl ester 141 (325 mg, lmmol), <strong>[4363-35-3]styrylboronic acid</strong> (300 mg, 2mmol), tetrakis-(triphenylphosphin)-palladium(0) (115.5 mg, 0.1 mmol), Na2CO3 (233 mg, 2.2mmol), toluene (5mL) and a magnetic stir bar were placed in a 10-mL microwave glass tube. The vessel was sealed with a septum and placed into the microwave cavity. Microwave irradiation of 60 W was used, the temperature being ramped from room temperature to 120 0C. Once 120 0C was reached, the reaction mixture was held for 10 min. Then the mixture was allowed to cool to room temperature, the reaction vessel was opened and the solvent was evaporated under pressure. The oily residue was purified by column chromatography on silica gel eluting with CtbCk/MeOH (90: 10). The final product was crystallised from the mixture of diethyl ether/petroleum ether and obtained as a yellow crystalline powder (101.1 mg, 0.2 mmol, 39%).M.p.: 174- 175 C IR (KBr): 3021, 2945, 2771, 2661, 2589, 1728, 1589, 1547, 1224, 960 cm '1H NMR (500 MHz, DMSCW6) delta 9.81 (s, 1 H, NH); 7.70 (s, 1 H, H2'); 7.59 (d, 3J = 7.1 Hz, 2 H, H2" + H6"); 7.44 (d, J = 7.3 Hz, 1 H, H6'); 7.37 (t, 3J = 7.4 Hz, 3 H, H3" + H5" + <n="96"/>H5'); 7.26 - 7.29 (m, 2 H, H4' + H4"); 7.20 (d, 3J = 16.6 Hz5 1 H, -CH=); 7.13 (d, 3J = 16.6 Hz, 1 H5-CH=); 4.93 - 5.00 (m5 1 H, H3); 3.68 (ddd, J = 2.1 Hz, J = 8.4 Hz, J = 13.7 Hz, 1 H3 H2A); 3.15 - 3.25 (m, 5 H, H2B + H6 + H8); 2.28 (sx, J = 2.9 Hz, 1 H, H4); 1.73 - 1.91 (m, 4 H, H5 + H7)13C NMR (125 MHz, DMSO-^) delta 153.0 (C=O); 139.3 (Cl'); 137.7 (C3'); 136.9 (Cl"); 129.2, 128.8 (C3" + C5"); 128.7 (-CH=); 128.5 (C5'); 127.9 (C4"); 126.7 (C2" + C6"); 121.2 (C4'); 118.03 (C6'); 116.5 (C2'); 67.6 (C3); 53.1 (C2); 45.9 (C8); 45.1 (C6); 24.0 (C4); 20.2 (C7); 16.9 (C5) MS (EI) m/z 348.2 (100) [M+]Anal, calcd. for C22H24N2O2 (348.45): C, 75.83; H, 6.94; N5 8.04Found C, 75.68; H, 6.96; N, 8.23.

Reference： [1]Patent: WO2007/100430,2007,A2 .Location in patent: Page/Page column 94-95

15
[ 948828-19-1 ]
[ 4363-35-3 ]
[ 1032737-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 160℃; for 0.166667h;Microwave irradiation;	A 3 mL Smith Process Vial was charged with 6-bromo-3 -ethyl thieno [2,3- b]pyrimidine-2,4-dione (48.8 mg, 0.1688 mmol), 2-phenylethenylboronic acid (70.0 mg, 0.422 mmol, 2.5 equiv) and Pd(Ph3P)4 (9.8 mg, 0.00844 mmol, 0.05 equiv) under argon atmosphere. Into the flask were added DME (2 mL) and 2M-Na2CO3 (0.5 mL) at room temperature so that concentration of the starting material becomes 0.07 M. The mixture was heated by microwave reactor at 1600C for 10 min. (Emrys Optimizer microwave, Smith Process Vial and Emrys Optimizer are registered trademarks of Personal chemistry, Inc., Uppsala). The mixture was filtered through Celite (3 g) and the Celite was washed with EtOAc (70 mL). The filtrate was washed with brine (30 mL) and dried with Na2SO4. After filtering off the drying agent, the solvent was removed under reduced pressure to give a crude mixture. Purification by recrystallization of the crude mixture from AcOEt (4 mL) afforded the 3-ethyl-5-methyl-6-(E-2-phenylethenyl}thieno[2,3- b]pyrimidine-2,4-dione as a light brown powder.1H NMR: (400 MHz, CDCl3)1.30 (3H, t, J = 7.0 Hz, NCH2CH5), 2.60 (3H, s, C(S)Me), 4.09 (2H, q, J = 7.0 Hz, NCH2CH3), 6.71 (IH, d, J= 16.0 Hz, -CH=CH-Ph), 7.25 (1eta, d, J= 16.0 Hz, -CH=CH- Ph), 7.27 (IH, bd t, J = 7.8 Hz, C(4")H), 7.36 (2H, br t, J = 7.8 Hz, C(3")H+C(5")H), 7.46 (2H, br d, J= 7.8 Hz, C(2")H+C(6")H)Attorney Docket No. 06-0227-WO 38 06-0227 <n="40"/>MS (EI): 313 (M++1), 284, 261, 182

Reference： [1]Patent: WO2008/70529,2008,A2 .Location in patent: Page/Page column 38-39

16
[ 59995-47-0 ]
[ 4363-35-3 ]
(3R,4S)-3-hydroxy-4-styrylcyclopentanone [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 6650 - 6653
Angewandte Chemie,2009,vol. 121,p. 6778 - 6781

17
[ 13466-38-1 ]
[ 4363-35-3 ]
[ 1198415-92-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	With potassium carbonate;palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃;Inert atmosphere;	Following general procedure E, compound 57 was synthesized (yield of first step 51%; yield of second step 17%). MS-ESI: m/z=274.3 [M+1]+ ; General procedure E: (Alternative Suzuki coupling reaction conditions) To a solution of <strong>[13466-38-1]5-bromo-2-hydroxypyridine</strong> (1 eq.), corresponding boronic acid (1.2 eq), potassium carbonate (3.5 eq) and tricyclohexylphosphine (0.1 eq) in toluene/water (2:1, v:v) under nitrogen atmosphere is added palladium acetate (0.05 eq). The mixture is heated to 100 C. for 2-3 h, and then cooled to room temperature, water is added and the mixture extracted with EA; the combined organics are washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by prep-TLC affords the desired 5-substituted-2-hydroxypyridine. The second coupling, a Suzuki coupling, of the intermediate 5-substituted-2-hydroxypyridine with an aryl boronic acid is performed following General Procedure A, as described above.

Reference： [1]Patent: US2009/318455,2009,A1 .Location in patent: Page/Page column 66; 82

18
[ 1198416-39-5 ]
[ 4363-35-3 ]
[ 1198411-49-2 ]

Yield	Reaction Conditions	Operation in experiment
		Following general procedure D, compound 55 was prepared in 65% yield as a solid. MS-ESI: m/z=274.3 [M+1]+ ; General procedure D: For step 1, the procedure is the same as for general procedure A. For step 2, a solution of the intermediate benzyl protected phenol (3.5 g, 10.8 mmol) in methanol (200 ml) is added to a Pd/C (300 mg) catalyst under N2 atmosphere, and then stirred for 2 h under H2 atmosphere (1 atm, 25 C.). The catalyst is filtered off through a celite pad, and the filtrate is concentrated in vacuo to give the free phenolic hydroxyl. For step 3, a solution of the resulting phenol intermediate (2.2 g, 11.8 mmol) in dichloromethane (DCM, 120 mL) is added to triethylamine (1.7 g, 16.8 mmol) at -78 C., followed by the addition of trifluoromethanesulfonic anhydride (4.76 g, 16.9 mmol). The resulting mixture is stirred at -78 C. for 15 min and quenched with ammonium chloride solution (10 mL). After warming to room temperature, water (30 mL) and DCM (50 mL) are added and separated. The target product is obtained by washing the crude mixture with methanol. For step 4, a solution of trifluoromethanesulfonic acid intermediate (0.79 mmol ) and tetrakis(triphenylphosphine)palladium (0.011 g, 0.0095 mmol) in dimethoxyethane (DME, 1 mL) is stirred at room temperature for 15 min followed by the addition of the solution arylboronic acid (0.21 mmol) in DME (1 mL) and 2M sodium carbonate (1 mL). The resulting mixture is refluxed for 14 hr and cooled down to room temperature. Water and ethyl acetate are added. After separation, the aqueous layer is extracted with ethyl acetate. The combined ethyl acetate solution is dried over sodium sulfate and filtered. The filtrate is concentrated in vacuo to dryness. Target products are isolated by prep-TLC.

Reference： [1]Patent: US2009/318455,2009,A1 .Location in patent: Page/Page column 66; 81

19
[ 63071-13-6 ]
[ 4363-35-3 ]
[ 103-49-1 ]
C₂₈H₂₅ClN₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 4779 - 4782

20
[ 54221-96-4 ]
[ 4363-35-3 ]
[ 103-49-1 ]
C₂₉H₂₈N₂O [ No CAS ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 4779 - 4782

21
[ 853941-51-2 ]
[ 4363-35-3 ]
[ 1268631-81-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 80℃; for 2h;Inert atmosphere;	A mixture of aminopyrazinetriflate (9) (100 mg, 0.300 mmol) and boronic acid (90 mg, 0.600 mmol) and Pd(PPh3)4 (35 mg, 0.0300 mmol) and K3PO4 (127 mg, 0.600 mmol) in dioxane (2 mL) was heated to 80 C for 6 h. The mixture was treated with 1 N NaOH aq (1 mL) and 30% H2O2 (1 mL) for 1 h at room temperature to oxidize the residual borane. To this mixture, 1 N HCl aq (1 mL) was added for neutralization. The product was extracted with AcOEt (×3), washed with brine, and dried over Na2SO4. After evaporation, the residue was purified by column chromatography on silica gel with AcOEt/hexane (1:2) to give aminopyrazine (2f) (63 mg, 72%) as a pale yellow solid. 1H NMR (CDCl3, 400 MHz), delta 4.16 (2H, s, CH2Ph), 4.44 (2H, s, NH2), 7.10 (1H, d, J=15.8 Hz, CH-1'), 7.24-7.38 (6H, m, Ph), 7.50 (1H, d, J=15.8 Hz, CH-2'), 7.54-7.56 (4H, m, Ph), 8.02 (1H, s, CH-6) ppm. 13C NMR (CDCl3, 150 MHz), delta 41.3, 124.8, 126.7, 127.1, 127.7, 128.5, 128.7, 129.0, 129.6, 136.6, 137.1, 139.4, 141.0, 141.2, 151.7 ppm. FAB-MS (NBA) m/z 288 (MH+). HRMS (FAB/NBA) calcd for C19H18N3 288.1561, found 288.1507 (MH+).

Reference： [1]Tetrahedron,2011,vol. 67,p. 1150 - 1157

22
[ 1268631-67-9 ]
[ 4363-35-3 ]
8-benzyl-2-(4-hydroxybenzylidene)-6-styrylimidazo[1,2-a]-pyrazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 40℃; for 1h;Inert atmosphere;	A round bottomed flask was charged with coelenterazinetriflate (11) (25 mg, 0.0507 mmol), boronic acid (15 mg, 0.114 mmol), Pd(PPh3)4 (7 mg, 0.00507 mmol), and K3PO4 (22 mg, 0.114 mmol) and connected to a vacuum/argon line. The flask was evacuated and then filled with argon, this evacuation/filling cycle being conducted three times. These reagents were dissolved in dioxane (1 mL) and then heated to 40 C for 1 h. The mixture was extracted with AcOEt (×3) and dried over Na2SO4. After evaporated, the residue was purified by preparative TLC to give dehydrocoelenterazine (14f) (14.0 mg, 54%) as a purple solid. IR (KBr) numax 3552, 1710, 1562, 1513, 1405 cm-1. 1H NMR (DMSOd6, 400 MHz), delta 4.37 (2H, s, CH2Ph), 6.76 (2H, d, J=8.4 Hz, Ph-OMe), 7.17-7.54 (10H, m, Ph), 7.33 (1H, d, J=14.3 Hz, CH-1'), 7.44 (1H, d, J=14.3 Hz, CH-2'), 7.59 (1H, s, CH-5), 7.71 (2H, d, J=8.4 Hz, Ph-OMe) ppm. 13C NMR (pyridine-d5, 100 MHz), delta 39.9, 113.4, 116.8, 117.4, 123.0, 124.0, 124.3, 126.7, 127.0, 127.1, 127.2, 128.1, 128.8, 129.2, 130.3, 130.4, 132.7, 133.4, 137.0, 137.4, 137.7, 158.1, 163.4, 166.0 ppm. FAB-MS (NBA) m/z 432 (MH+). HRMS (FAB/NBA) calcd for C28H22N3O2 432.1712, found 432.1666 (MH+).

Reference： [1]Tetrahedron,2011,vol. 67,p. 1150 - 1157

23
[ 1262133-21-0 ]
[ 4363-35-3 ]
C₂₅H₂₄ClNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 80℃; for 3h;	Step 7-3 The compound (15 g) obtained in step 7-2 and 1,4-dioxane (150 ml) were mixed, potassium carbonate (18 g), phenylvinylboric acid (7.1 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (1:1) (1.8 g) and water (45 ml) were added and the mixture was stirred at 80 C. for 1.5 hr with heating. Phenylvinylboric acid (0.64 g) was added and the mixture was stirred for 1.5 hr. The mixture was cooled to room temperature, and water, ethyl acetate and saturated brine were added to separate the organic layer. The organic layer was concentrated under reduced pressure and the obtained residue was purified by column chromatography (eluent: chloroform). To the obtained solid was added isopropyl alcohol (100 ml) and the mixture was slurried at 70 C. for 0.5 hr and under ice-cooling to give the compound described in the above-mentioned scheme (11.5 g, 62%).1H-NMR (CDCl3) delta: 1.55 (s, 9H), 5.21 (s, 2H), 6.87 (s, 1H), 7.01 (d, 1H, J=15.9 Hz), 7.30-7.44 (m, 8H), 7.56 (d, 2H, J=7.1 Hz), 7.65 (d, 1H, J=16.1 Hz).

Reference： [1]Patent: US2011/77267,2011,A1 .Location in patent: Page/Page column 38-39

24
[ 591-50-4 ]
[ 4363-35-3 ]
[ 103-30-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In ethanol; at 80℃; for 3h;Inert atmosphere;	General procedure: A mixture of 1a (102 mg, 0.5 mmol), phenylboronic acid 2a(91.4 mg, 0.75 mmol), and K2CO3(138 mg, 1.0 mmol) in EtOH (3 mL) was heated in the presence of SGlPd at 80C for 3 h under argon an atmosphere without stirring. After the reaction mixture was cooled to room temperature, the SGlPd was removed from the reaction mixture and rinsed several time with EtOH. The raction mixture was poured into 2 MNaOH aq., extracted with AcOEt. The organic layer was washed with sat. aq. NH4Cl, and sat. aq. NaCl, dried over anhydrous NaSO4. Concentration at reduced pressure gave yellowish oil, which was chromatographed on silica gel with hexane as the eluent to give the biphenyl (3a, 77.1 mg, 99%) as a colorless solid. The recovered SGlPd catalyst was again subjected to next reaction for second run. The procedure was repeated a total 10 runs.

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 1154 - 1160
[2]Advanced Synthesis and Catalysis,2011,vol. 353,p. 743 - 748

25
[ 696-62-8 ]
[ 4363-35-3 ]
[ 4333-75-9 ]
[ 1694-19-5 ]

Yield	Reaction Conditions	Operation in experiment
19%; 71%	With Pd(OH)2/Fe3O4; sodium carbonate; In toluene; at 130℃; for 24h;	General procedure: To a stirred solution of aromatic iodide (1, 1 mmol) in toluene (2 mL) were added Pd(OH)2/Fe3O4 (50 mg, 1.2 mol % of Pd), Na2CO3 (3 mmol, 318 mg), and the corresponding boronic acid (2 or 4, 3 mmol). The resulting mixture was stirred at 130 C for 1 h. The catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The corresponding products 3 or 5 were usually purified by chromatography on silica gel (hexane/ethyl acetate).

Reference： [1]Tetrahedron,2011,vol. 67,p. 5432 - 5436

26
[ 13816-02-9 ]
[ 4363-35-3 ]
1-phenyl-4-(2-thiazolyl)-1-butene [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 669 - 673

27
[ 772-03-2 ]
[ 4363-35-3 ]
1-phenyl-4-(2-quinolyl)-1-butene [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 669 - 673

28
[ 1352342-51-8 ]
[ 4363-35-3 ]
[ 1352342-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;[1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); In 1,4-dioxane; at 140℃; for 1h;	Compound C (0.500 g, 1.32 mmol), styrene boronic acid (0.292 g, 1.98 mmol), Pd(dppf)CI2 (0.107 mg, 0.134 mmol) and K3P04 (4 ml, 1 M solution) were combined in a 100 ml round bottom flask. The reaction vessel was placed under vacuum and then refilled with Ar three times. 1 ,4-dioxane (13 ml) was added to the solid mixture. The reaction vessel was heated to 140 C with stirring. The reaction was monitored by LC-MS, which showed complete conversion of the starting material after 1 hour. After the flask was cooled to room temperature, the mixture was concentrated under vacuum and re- dissolved in EtOAc. The organic solution was washed successively with concentrated NH4CI, water and brine and then dried over Na2SO4. The solution was concentrated under vacuum and the resulting solid was used in the next step without purification. MS [M+H]+ = 331.12.

Reference： [1]Patent: WO2011/156610,2011,A2 .Location in patent: Page/Page column 163

29
[ 4363-35-3 ]
[ 98495-62-6 ]
C₂₉H₄₄N₂O₆Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate; In tetrahydrofuran; at 50℃; for 24h;Inert atmosphere;	General procedure: Compound 1 (419 mg, 0.7 mmol), Pd(PPh3)4 (49 mg, 0.042 mmol), CuTC (147 mg, 0.77 mmol), and 4-fluorophenylboronic acid (118 mg, 0.84 mmol) were flushed with Ar and subsequently suspended in dry THF (8 ml) under an Ar atmosphere. The reaction mixture was stirred at 50 C for 24 h and then allowed to cool to room temperature. The solvent was evaporated, and the residue was taken up in EtOAc (30 ml), and the organic layer was washed with satd NaHCO3 (2 × 20 ml) and brine (1 × 20 ml), dried over MgSO4, and evaporated. The residue was purified by silica gel column chromatography (0.5% EtOH in CH2Cl2) to yield the TIPDS-protected intermediate 2b (332 mg, 84%). 1H NMR (300 MHz, CDCl3) delta 8.56 (br s, 1H, NH), 7.43 (br s, 2H, ArH), 7.18 (t, 2H, J = 8.6 Hz, ArH), 5.55 (s, 1H, H-5), 5.51 (dd, 1H, J = 9.5, 3.1 Hz, H-1'), 4.97 (m, 1H, H-3'), 4.08-3.92 (m, 2H, H-5'), 3.67 (m, 1H, H-4'), 2.94-2.83 (m, 1H, H-2'), 2.24-2.10 (m, 1H, H-2'), 1.15-0.96 (m, 28H, 4 × i-propyl). 13C NMR (75 MHz, CDCl3) delta 163.98 (d, JCF = 251 Hz), 162.19, 155.93, 149.76, 130.24 (d, JCF = 8.3 Hz), 129.33 (d, JCF = 3.8 Hz), 116.47 (d, JCF = 22.5 Hz), 104.08, 86.50, 86.24, 73.76, 64.23, 39.79, (17.69, 17.57, 17.50, 17.47, 17.29, 17.12: 8 C), 13.42, 13.36, 12.83, 12.71. MS (ESI) calcd for C27H41FN2O6Si2 587.24 (M+Na+), 1151.49 (2 M+Na+); found 587.12, 1151.62.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 253 - 255

30
[ 4363-35-3 ]
[ 68-12-2 ]
[ 1885-38-7 ]
[ 24840-05-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 2528 - 2531

31
[ 1373125-68-8 ]
[ 4363-35-3 ]
C₃₃H₃₀F₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; In water; toluene; at 90℃; for 14h;	General procedure: The arylbromide (122 mg, 0.3 mmol), 3-methoxy-phenylboronic acid (137 mg, 0.900 mmol), potassium phosphate (191 mg, 0.900 mmol), Pd2(dba)3 (6.87 mg, 0.008 mmol), and tri-tert-butylphosphonium tetrafluoroborate (8.70 mg, 0.030 mmol) were combined in a mixture of degassed toluene (0.81 ml) and water (0.09 ml) and heated to 90 C for 14 h. At this time LC-MS showed a complete reaction. The reaction was cooled, diluted with ethyl acetate, and filtered through a small pad of silica gel eluting with ethyl acetate. The crude solution was concentrated and purified by silica gel chromatography (Biotage 25 g SNAP cartridge; 0-10% ethyl acetate in hexanes) to afford a clear viscous oil (121 mg, 93%).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2308 - 2311

32
[ 141-79-7 ]
[ 4363-35-3 ]
[ 435276-29-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With trifluoroacetic anhydride; In dichloromethane; at 60℃; for 18h;	General procedure: To a stirred solution of boronic acid 1 (1.25 equiv) and 2 (1.0 equiv) in anhydrous CH2Cl2 (1.6 mL/mmol 1) was added trifluoroacetic anhydride (0.3 equiv). After stirring overnight (18 h), a saturated solution of Na2CO3 was added. The layers were separated and the aqueous one was extracted with Et2O. The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography over silica gel (hexane/CH2Cl2 25:75).