[ CAS No. 15016-43-0 ] {[proInfo.proName]}

Name: 15016-43-0|(3-Vinylphenyl)boronic acid|95%
Brand: Ambeed
SKU: A201221
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2D 3D

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Quality Control of [ 15016-43-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 15016-43-0 ]

SDS Specification

Alternatived Products of [ 15016-43-0 ]

Product Details of [ 15016-43-0 ]

CAS No. :	15016-43-0	MDL No. :	MFCD01074679
Formula :	C₈H₉BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SYBQEKBVWDPVJM-UHFFFAOYSA-N
M.W :	147.97	Pubchem ID :	4366886
Synonyms :

Calculated chemistry of [ 15016-43-0 ]

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 Å²

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 :	2.0

Safety of [ 15016-43-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 15016-43-0 ]

* 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 [ 15016-43-0 ]

[ 15016-43-0 ] Synthesis Path-Downstream 1~56

1
[ 15016-43-0 ]
[ 111-42-2 ]
[ 96533-80-1 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 2598 - 2603

4
[ 109-04-6 ]
[ 15016-43-0 ]
[ 478944-02-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; In tetrahydrofuran;	EXAMPLE 2 Preparation of 2-(3-vinyl-phenyl)pyridine The reaction was performed with <strong>[15016-43-0]3-vinyl-phenylboronic acid</strong> (10 g, 0.0676 mol), 2-bromopyridine (12.64 g, 0.08 mol), tetrahydrofuran (100 ml), 2M potassium carbonate aqueous solution (26 ml), and tetrakis(triphenylphosphine) palladium (Pd(Ph3)4, 0.06 g, 1 mol %) according to Example 1. The yield was 80%.

Reference： [1]Patent: US2002/198346,2002,A1

5
[ 15016-43-0 ]
[ 76-05-1 ]
2-amino-3-methyl-6-(3'-vinyl-biphenyl-3-ylmethyl)-3H-pyrimidin-4-one trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		2-Amino-3-methyl-6-(3'-vinyl-biphenyl-3-ylmethyl)-3H-pyrimidin-4-one (Scheme 9, D); A thick-walled glass vial was charged with a stir bar, 2-arnino-6-(3-bromo-benzyl)-3-methyl-3H-pyrimidin-4-one (Scheme 9, C) (120 mg, 0.2 mmol), <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (46 mg, 0.39 mmol), dichlorobis(triphenylphosphine)-palladium (II) (approximately 6 mg, 0.006 mmol), Cs2C03 (246 mg, 0.76 mmol) and DME/H20/EtOH (7:3:2; 5 mL). The vial was crimp sealed and subjected to microwave radiation for 5 min at 150 C. The resultant black slurry was filtered, washed with methanol (3x3 mL) then concentrated in vacuo. The resultant residue was then purified by reverse phase HPLC. Appropriate fractions were concentrated via centrifugal evaporation to afford the white trifluoroacetic acid salt of the title compound (62 mg, 35%). *H NMR (300 MHz, DMSO-^/TFA-d) 5 3.27 (s, 3H), 3.93 (s, 2H), 5.33 (d, J = 11.0 Hz, 1H), 5.93 (d, J = 17.7 Hz, 1H), 5.98 (s, 1H), 6.83 (dd, J = 17.7, 11.0 Hz, 1H), 7.36 - 7.52 (m, 4H), 7.59 (d, J = 16.8 Hz, 1H), 7.62 (d, J = 17.2 Hz, 1H), 7.72 - 7.73 (m, 2H); m/z (APCI+) M+l = 318.2; fe = 2.17 min.

Reference： [1]Patent: WO2006/41405,2006,A1 .Location in patent: Page/Page column 144-146

6
[ 883892-48-6 ]
[ 15016-43-0 ]
2-amino-3-methyl-6-(3'-vinyl-biphenyl-3-ylmethyl)-3H-pyrimidin-4-one trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 150℃; for 0.0833333h;Microwave irradiation;	2-Amino-3-methyl-6-(3'-vinyl-biphenyl-3-ylmethyl)-3H-pyrimidin-4-one (Scheme 9, D); A thick-walled glass vial was charged with a stir bar, 2-amino-6-(3-bromo-benzyl)-3-methyl-3H-pyrimidin-4-one (Scheme 9, C) (120 mg, 0.2 mmol), <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (46 mg, 0.39 mmol), dichlorobis(triphenylphosphine)-palladium (II) (approximately 6 mg, 0.006 mmol), Cs2CO3 (246 mg, 0.76 mmol) and DME/H2O/EtOH (7:3:2; 5 mL). The vial was crimp sealed and subjected to microwave radiation for 5 min at 150 0C. The resultant black slurry was filtered, washed with methanol (3 x 3 mL) then concentrated in vacuo. The resultant residue was then purified by reverse phase HPLC. Appropriate fractions were concentrated via centrifugal evaporation to afford the white trifluoroacetic acid salt of the title compound (62 mg, 35%).

Reference： [1]Patent: WO2006/41404,2006,A1 .Location in patent: Page/Page column 131

7
2,3-diazabicyclo[2.2.1]hept-5-ene-N,N'-di-tert-butyl dicarboxylate [ No CAS ]
[ 201230-82-2 ]
[ 15016-43-0 ]
C₂₄H₃₂N₂O₅ [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 5365 - 5367

8
[ 488-48-2 ]
[ 15016-43-0 ]
[ 1175489-18-5 ]

Yield	Reaction Conditions	Operation in experiment
62%		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.

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 4651 - 4653
[2]Tetrahedron,2013,vol. 69,p. 460 - 469

9
[ 488-48-2 ]
[ 15016-43-0 ]
[ 1175489-18-5 ]
C₃₈H₃₀O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃; for 12h;Inert atmosphere;	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.

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 4651 - 4653
[2]Tetrahedron,2013,vol. 69,p. 460 - 469

10
[ 67-56-1 ]
[ 108-86-1 ]
[ 201230-82-2 ]
[ 15016-43-0 ]
[ 57872-48-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 2437 - 2442

11
[ 108-86-1 ]
[ 201230-82-2 ]
[ 15016-43-0 ]
[ 63444-57-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 2437 - 2442

12
[ 108-86-1 ]
[ 201230-82-2 ]
[ 15016-43-0 ]
[ 22071-15-4 ]
[ 41652-24-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 2437 - 2442

13
[ 108-86-1 ]
[ 201230-82-2 ]
[ 15016-43-0 ]
[ 18107-18-1 ]
[ 57872-48-7 ]
3-(3-Benzoyl-phenyl)-propionic acid methyl ester [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 2437 - 2442

14
[ 1198165-55-7 ]
[ 15016-43-0 ]
[ 1198165-56-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 80℃;Inert atmosphere;	b) Preparation of 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propyl-3'-vinylbiphenyl; To a solution of 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenyl trifluoromethanesulfonate (238 mg, 497 mumol) in 1,4-dioxan, potassium phosphate (401 mg), <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (88 mg), and tetrakis triphenylphosphine palladium complex (57 mg) were added at room temperature under an argon atmosphere, and the resultant mixture was heated at 80 C. After completion of the reaction, the reaction solution was neutralized by adding water and 2 mol/L of hydrochloric acid, extracted with ethyl aceate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and the title compound (175 mg, yield 81%) was obtained as a colorless oil.1H-NMR (CDCl3) delta: 0.82 (3H, t, J=7.3 Hz), 1.53-1.64 (2H, m), 2.57 (2H, t, J=7.6 Hz), 3.58 (3H, s), 4.89 (2H, s), 5.30 (1H, dd, J=0.5, 10.8 Hz), 5.76 (1H, dd, J=0.5, 17.6 Hz), 6.70 (1H, dd, J=10.8, 17.6 Hz), 6.30-7.55 (7H, m).

Reference： [1]Patent: US2010/48610,2010,A1 .Location in patent: Page/Page column 54

15
[ 1191429-56-7 ]
[ 15016-43-0 ]
[ 1176788-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6489 - 6493

16
[ 108-36-1 ]
[ 15016-43-0 ]
[ 1219700-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;Pd(PPh3)3; In 1,2-dimethoxyethane; nitrogen; water; ethyl acetate;	Step 1 A solution of 1,3-dibromobenzene (5.3 mL, 43.9 mmol), potassium carbonate (14.0 g, 101 mmol) and <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (5 g, 33.8 mmol) in DME (100 mL) and water (20 mL) (in a pressure vessel) was sparged with nitrogen for 15 min. Pd(PPh3)3 (1.17 g, 1.014 mmol) was added and then the reaction was heated to 80 C. overnight. The reaction was cooled to r.t. and evaporated on the rotovap. The residue was diluted in EtOAc and washed with water then brine, dried over MgSO4, filtered and evaporated to give the crude material. The crude material was purified by flash chromatography on the Biotage (0-5% EtOAc:Hex) to give 3-bromo-3'-vinylbiphenyl (5.21 g, 20.10 mmol, 60% yield) as a clear liquid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 5.33 (d, J=10.79 Hz, 1H) 5.84 (dd, J=17.57, 0.75 Hz, 1H) 6.80 (dd, J=17.57, 10.79 Hz, 1H) 7.32 (t, J=7.78 Hz, 1H) 7.38-7.48 (m, 3H) 7.51 (dddd, J=13.24, 7.84, 1.76, 1.00 Hz, 2H) 7.56-7.61 (m, 1H) 7.76 (t, J=1.88 Hz, 1H).

Reference： [1]Patent: US2010/80771,2010,A1

17
[ 32381-28-5 ]
[ 15016-43-0 ]
methyl N-acetyl-S-(3-vinylphenyl)cysteinate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 6336 - 6340

18
[ 15016-43-0 ]
[ 23030-50-4 ]
2,5-dimethoxy-3-(3-vinylphenyl)-1,4-benzoquinone [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 1233 - 1241

19
[ 7657-09-2 ]
[ 15016-43-0 ]
[ 1343404-86-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 70℃; for 8h;Inert atmosphere;	General procedure: The reaction was carried out in a pressure tube. To a dioxane suspension (5 mL) of the <strong>[7657-09-2]1,4-dibromo-2-(trifluoromethyl)benzene</strong> (6), Pd(PPh3)4 (3-5 mol%) and of the arylboronic acid (2) was added an aqueous solution of K2CO3 (2 M, 1-2 mL). The mixture was heated at the indicated temperature (70 8C) under Argon atmosphere for the indicated period of time (8 h). The solution was cooled to 20 C, poured into H2O and CH2Cl2 (5 mL each), and the organic and the aqueous layers were separated. The later was extracted with CH2Cl2 (3 15 mL). The combined organic layers were washed with H2O (3 10 mL), dried (Na2SO4), and concentrated in vacuo. The residue was purified by chromatography (flash silica gel, heptanes/EtOAc) to give 4-bromo-3-(trifluoromethyl)biphenyls (7a-o) (79-94%).

Reference： [1]Synlett,2011,p. 1895 - 1899
[2]Journal of Fluorine Chemistry,2013,vol. 145,p. 18 - 34

20
[ 15016-43-0 ]
[ 79-10-7 ]
[ 1352089-94-1 ]

Reference： [1]Synlett,2011,p. 2517 - 2520

21
[ 1353010-46-4 ]
[ 15016-43-0 ]
[ 1353010-55-5 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 6670 - 6684

22
[ 76-09-5 ]
[ 15016-43-0 ]
4,4,5,5-tetramethyl-2-(3-vinylphenyl)-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With magnesium 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.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 8050 - 8060
[2]Polymer,2011,vol. 52,p. 2485 - 2491
[3]Tetrahedron Letters,2013,vol. 54,p. 1211 - 1217

23
[ 7660-25-5 ]
[ 15016-43-0 ]
[ 1313544-01-2 ]

Reference： [1]Polymer,2011,vol. 52,p. 2485 - 2491

24
[ 1226760-36-6 ]
[ 15016-43-0 ]
C₂₁H₁₈ClNO₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4205 - 4219

25
[ 1402051-60-8 ]
[ 15016-43-0 ]
[ 1402051-77-7 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 3759 - 3763

26
[ 1400877-47-5 ]
[ 15016-43-0 ]
[ 1400876-83-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 90℃; for 2h;Product distribution / selectivity;	Step 2: (R)-4-( 1 -cyclopropylethylamino)-6-(3 -vinylphenyl)pyrrolo[ 1 ,2-b]pyridazine- 3-carboxamide[00276] To a degassed solution of (R)-6-bromo-4-(l- cyclopropylethylamino)pyrrolo [l,2-b]pyridazine-3-carboxamide (100 mg, 0.309 mmol), <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (137 mg, 0.928 mmol) and K2CO3 (0.464 mL, 0.928 mmol) in DME (Volume: 2 mL) was added Pd(Ph3P)4 (21.45 mg, 0.019 mmol). The reaction mixture was heated to 90 C for 2 hrs. The reaction mixture was diluted with 10 mL of EtOAc and then washed with 5 mL of water and 5 mL of brine. The organic phase was concentrated to yield a crude product which was purified on prep silica gel TLC plate with hexanes/EtOAc(2/l) to yield a product. It was triturated in MeOH. The solid was collected as the desired product (79.7 mg, 74% yield). MS (ES+) m/z: 347.3 (M+H); HPLC: 86%, retention time: 3.808 min (analytical HPLC Method B).

Reference： [1]Patent: WO2012/125887,2012,A1 .Location in patent: Page/Page column 162-163

27
[ 1394235-81-4 ]
[ 15016-43-0 ]
[ 1403579-12-3 ]

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6434 - 6441,8

28
[ 1394235-81-4 ]
[ 15016-43-0 ]
[ 1410123-88-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In ethanol; water; toluene; for 1h;Reflux;	General procedure: To a solution of bromide 4 (52.8 mg, 0.15 mmol) and 4-(methoxycarbonyl)phenylboronic acid (32.4 mg, 0.18 mmol) in a mixture of toluene (1.5 mL), EtOH (0.9 mL) and 1 M aq K2CO3 (1.5 mL) was added Pd(PPh3)4 (6.9 mg, 4 mol %) and PdCl2(dppf)·CH2Cl2 (3.7 mg, 3 mol %). After being stirred under reflux for 1 h, the mixture was extracted with CHCl3. The organic layers were dried over MgSO4 and concentrated. The residue was purified by flash chromatography over aluminum oxide with n-hexane/EtOAc (10:0/9:1) to give the compound 5a as colorless solid (47.3 mg, 77%).

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6434 - 6441,8

29
[ 76-09-5 ]
[ 15016-43-0 ]
[ 1422172-91-5 ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1211 - 1217

30
[ 5034-74-2 ]
[ 15016-43-0 ]
5-(3'-vinylphenyl)-3-methoxysalicylaldehyde [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 5950 - 5960

31
[ 15016-43-0 ]
N,N'-bis(5-(3′-vinylphenyl)-3-methoxysalicylidene)ethylene-1,2-diamine [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 5950 - 5960

32
[ 1375111-55-9 ]
[ 15016-43-0 ]
rac-(3aR,7aR,E)-7a-methyl-3-(3-vinylbenzylidene)-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 5566 - 5571

33
[ 141-32-2 ]
[ 15016-43-0 ]
(E)-butyl 3-(3-vinylphenyl) acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [bmpy]2[PdCl4]; In N,N-dimethyl-formamide; at 130℃; for 3h;Microwave irradiation;	General procedure: The oxidative Heck reaction was carried out in a 50 mL Schlenk tube. The solid substrates: phenylboronic acid (1.5 mmol, 0.184 g) and palladium complex (0.02 mmol) were weighted and placed in the Schlenk tube which was evacuated and filled with oxygen. Next,olefin (1 mmol) and 5 mL of the solvent saturated with oxygen (30 min) were added with a pipette in the atmosphere of oxy-gen. The reactor was closed with a rubber plug and the reaction mixture was stirred in 130C. After the given reaction time, the reactor was cooled down and the organic products were extracted with 20 mL of diethyl ether. For better phase separation 1 mL of water was added; 0.15 mL of mesitylene was added as an internal standard. The organic products were analyzed using the GC-MS method.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2015,vol. 408,p. 1 - 11

34
1,4-bis(trifluoromethylsulfonyl-oxy)-9H-fluoren-9-one [ No CAS ]
[ 15016-43-0 ]
C₂₂H₁₃F₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 60℃; for 12h;Inert atmosphere;	General procedure: In a pressure tube 2 (0.525 mmol), K3PO4 (2.0 equiv), Pd(PPh3)4(3.0 mol%), and arylboronic acid (1.2 equiv) were mixed withdry 1,4-dioxane, degassed with argon und stirred for 12 h at60 C. After cooling to r.t., the solution was filtered throughCelite, washed with CH2Cl2, and the filtrate was concentrated byreduced pressure. The residue was purified by column chromatographyto receive the monosubstituted fluorenone 5a-h ingood yields.

Reference： [1]Synlett,2016,vol. 27,p. 75 - 79

35
2,2-dimethyl-6,7-ditriflyloxychroman-4-one [ No CAS ]
[ 15016-43-0 ]
C₂₇H₂₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90℃; for 24h;Inert atmosphere;	General procedure: To a mixture of 2,2-dimethyl-6,7-ditriflyloxychroman-4-one(150 mg, 0.318 mmol), K3PO4 (202 mg, 0,95 mmol), and boronic acid (0.70 mmol) in dry 1,4-dioxane (4 mL) was added Pd(PPh3)4 (22 mg, 0.019 mmol) in a dried pressure tube under argon. The reaction mixture was stirred and heated in an aluminium heating block. The solvent was evaporated in vacuum, and the solid mixture was submitted to adsorptive filtration on silicagel using acetone as eluent removing the inorganic compounds. Silica was added to the solution, the acetone was evaporated,and the mixture was purified by column chromatography (eluent:heptane-EtOAc, the ratio is given below) giving the diarylated product.

Reference： [1]Synlett,2016,vol. 27,p. 1073 - 1076

36
2,2-dimethyl-6,7-ditriflyloxychroman-4-one [ No CAS ]
[ 15016-43-0 ]
C₂₀H₁₇F₃O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 60℃; for 5h;Inert atmosphere;	General procedure: To a mixture of 2,2-dimethyl-6,7-ditriflyloxychroman-4-one(150 mg, 0.318 mmol), K3PO4 (135 mg, 0,64 mmol), and boronic acid (0.349 mmol) in dry 1,4-dioxane (4 mL) was added Pd(PPh3)4 (11 mg, 0.0095 mmol) in a dried pressure tube under argon. The reaction mixture was stirred and heated in an aluminium heating block. The solvent was evaporated in vacuum,then the solid mixture was submitted to adsorptive filtration on silica gel using acetone as eluent removing the inorganic compounds. Silica was added to the solution, the acetone was evaporated,and the mixture was purified by column chromatography(eluent: heptane-EtOAc mixture, the ratio is given below) giving the monosubsituted product.

Reference： [1]Synlett,2016,vol. 27,p. 1073 - 1076

37
[ 1273-73-0 ]
[ 15016-43-0 ]
1-(3-vinylphenyl)ferrocene [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 39947 - 39954

38
[ 1293-65-8 ]
[ 15016-43-0 ]
1,1'-bis(3-vinylphenyl)ferrocene [ No CAS ]