[ CAS No. 143418-49-9 ] {[proInfo.proName]}

Name: 143418-49-9|(3,4,5-Trifluorophenyl)boronic acid|98%
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Quality Control of [ 143418-49-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 143418-49-9 ]

SDS Specification

Alternatived Products of [ 143418-49-9 ]

Product Details of [ 143418-49-9 ]

CAS No. :	143418-49-9	MDL No. :	MFCD02093069
Formula :	C₆H₄BF₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UHDDEIOYXFXNNJ-UHFFFAOYSA-N
M.W :	175.90	Pubchem ID :	2734671
Synonyms :		Chemical Name :	(3,4,5-Trifluorophenyl)boronic acid

Calculated chemistry of [ 143418-49-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	36.14
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.13
Log Po/w (WLOGP) :	1.04
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	0.58
Consensus Log Po/w :	0.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.95
Solubility :	1.99 mg/ml ; 0.0113 mol/l
Class :	Very soluble
Log S (Ali) :	-1.57
Solubility :	4.7 mg/ml ; 0.0267 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.12
Solubility :	1.33 mg/ml ; 0.00753 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.18

Safety of [ 143418-49-9 ]

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

Application In Synthesis of [ 143418-49-9 ]

* 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.

Upstream synthesis route of [ 143418-49-9 ]
Downstream synthetic route of [ 143418-49-9 ]

[ 143418-49-9 ] Synthesis Path-Upstream 1~6

1
[ 121-43-7 ]
[ 138526-69-9 ]
[ 143418-49-9 ]

Reference： [1] Zeitschrift fur Anorganische und Allgemeine Chemie, 2002, vol. 628, # 13, p. 2827 - 2833
[2] Patent: US2011/105766, 2011, A1, . Location in patent: Page/Page column 4

2
[ 5419-55-6 ]
[ 138526-69-9 ]
[ 143418-49-9 ]

Reference： [1] Journal of Organometallic Chemistry, 2000, vol. 598, # 1, p. 127 - 135

3
[ 138526-69-9 ]
[ 143418-49-9 ]

Reference： [1] Patent: EP1191008, 2002, A1, . Location in patent: Page 71

4
[ 121-43-7 ]
[ 156006-28-9 ]
[ 143418-49-9 ]

Reference： [1] Organic Syntheses, 2002, vol. 79, p. 176 - 176

5
[ 223440-94-6 ]
[ 7732-18-5 ]
[ 143418-49-9 ]

Reference： [1] Zeitschrift fur Anorganische und Allgemeine Chemie, 2002, vol. 628, # 13, p. 2827 - 2833
[2] Zeitschrift fur Anorganische und Allgemeine Chemie, 2002, vol. 628, # 13, p. 2827 - 2833

6
[ 143418-49-9 ]
[ 615-36-1 ]
[ 915416-45-4 ]

Reference： [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 44, p. 6566 - 6574
[2] Journal of the American Chemical Society, 2013, vol. 135, # 17, p. 6618 - 6625

[ 143418-49-9 ] Synthesis Path-Downstream 1~49

1
[ 86579-53-5 ]
[ 143418-49-9 ]
3',4',5'-trifluoro-4-(4-propylcyclohexyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 177 - 181

2
[ 35109-88-7 ]
[ 143418-49-9 ]
(2R,3R,4S,5R)-2-{6-amino-2-(3,4,5-trifluorophenyl)-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydrofuran-3,4-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With caesium carbonate In ethanol; toluene at 120℃; for 0.666667h; Microwave irradiation;	13 Example 13; Preparation of (2R.3R.4tS'.5R)-2-(6-amino-2-(3.4.5-trifluorophenyl)-9H-purin-9-yli-5-(hvdroxymethyl)tetrahydrofuran-3 ,4-diol 12; Scheme 12; A solution of 2-iodo adenosine (200mg, 0.51mmol), 3,4,5-trifluorophenylboronic acid (107mg, 0.609mmol), cesium carbonate (364mg, 1.12mmol) and Pd(PPlIs)4 (59mg, 0.051mmol) in toluene (1.2mL) and ethanol (2.4mL) was heated in a Biotage microwave (12O0C, absorption high, pre-stirring 30s) for 40min. The solvents were then removed in vacuo and the residue dissolved in EtOAc (3OmL) and washed with sat. aq. NaHCO3 (2OmL x2) and brine (2OmL) and dried over MgSO4. Purification by flash column chromatography (normal phase, ICN silica, 5Og, 18-32μ, gradient 2.5-15% ethanol in DCM, residue dry loaded, product eluted in 15% ethanol) and by reverse phase prep HPLC (Phenomenex Synergi, RP-Hydro 150 x 10mm, lOμ, 2OmL per min, gradient 5-100% acetonitrile in water over lOmin, product eluted in 50% acetonitrile) afforded (2R,3R,4lSr,5R)-2-{6-amino-2-(3,4,5-trifiuorophenyl)-9H-purin-9-yl}-5-(hydroxymethyl) tetrahydrofuran-3,4-diol 12 as a white solid (13.2mg, 7%).HPLC (Phenomenex Synergi, RP-Hydro, 15O x 4.6mm, 4u, 1.5mL per min, 3O0C, gradient 5-100% acetonitrile (+0.085% TFA) in water (+0.1% TFA) over 7min - held for 30s, 200- 300nm): Retention time 4.49min, 100%.LCMS (Phenomenex Synergi, RP-Hydro, 15O x 4.6mm, 4u, 1.5mL per min, 3O0C, gradient 5-100% acetonitrile (+0.085% TFA) in water (+0.1% TFA) over 7min - held for 30s, 200- 300nm): Retention time 5.04min, 100%, ES+: 398.396 [MH]+.

Reference： [1]Current Patent Assignee: BENEVOLENTAI LIMITED - WO2008/745, 2008, A2 Location in patent: Page/Page column 45

3
[ 126-30-7 ]
[ 143418-49-9 ]
5,5-dimethyl-2-(3,4,5-trifluorophenyl)-[1,3,2]dioxaborinane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 2,2-Dimethyl-1,3-propanediol; 3,4,5-trifluorophenylboronic acid In diethyl ether at 20℃; for 1h; Stage #2: With calcium chloride at 20℃; for 1h;	III. General Procedure for Preparation of Fluorine-Containing Arylboronate 2 General procedure: Fluorine-containing arylboronic acid and 2,2- dimethyl-1,3-propanediol (1.1-1.2 equiv) were dissolved in Et2O (0.1M). Thesolution was stirred for 1 h at room temperature under air. After the reaction, CaCl2 (3 equiv) was introduced to the mixture,which was then stirred for 1 h, filtered through Celite, and concentrated. The crude material was purified by silica gel columnchromatography (hexane:AcOEt = 10:1) to afforded fluorine-containing arylboronate 2.
34%	In toluene at 20℃; for 2h;	19 Example 19 (General procedure (A)); 5,5-Dimethyl-2-(3,4,5-trifluorophenyl)-[1,3,2]dioxaborinane The title compound (34%,yellow oil) was prepared from 3,4,5-trifluorophenylboronic acid and neopentylglycol. 1H NMR (300 MHz, CDCl3): δ 1.01 (s, 6H), 3.77 (s, 4H), 7.38 (t, 3H).1H NMR (300 MHz DMSO d6): δ 2.78-2.87 (m, 2H), 3.00-3.12 (m, 2H), 3.72-3.87 (m, 4H), 6.80 (s, 1 H), 6.92 (s, 1 H), 6.98 (bs, 1 H).
	In diethyl ether at 20℃; Inert atmosphere; Molecular sieve;	Synthesis of arylboronic esters: General procedure: To a Et2O solution of anorganoboronic acid (1.00 equiv) and 2,2-dimethylpropane-1,3-diol (neopentyl glycol)(1.02 equiv), 4A molecular sieves was added and the reaction mixture was stirred atroom temperature. After the reaction finished, the reaction mixture was filtered andconcentrated in vacuo. The residue was subjected to flash column chromatography(eluent: petroleum ether/ethyl acetate) or recrystallization to obtain the desired product

Reference： [1]Izumoto, Akiko; Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Synlett, 2017, vol. 28, # 19, p. 2609 - 2613]
[2]Current Patent Assignee: NOVO NORDISK A/S - WO2003/105860, 2003, A1 Location in patent: Page 32
[3]Liu, Kai; Li, Nian; Ning, Yunyun; Zhu, Chengjian; Xie, Jin [Chem, 2019, vol. 5, # 10, p. 2718 - 2730]

4
[ 14221-01-3 ]
[ 105931-73-5 ]
[ 143418-49-9 ]
[ 187804-77-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	With sodium hydrogencarbonate; potassium carbonate In 1,2-dimethoxyethane; water	4.s Preparation of 4-bromo-2,3',4',5'-tetrafluorobiphenyl (First stage) Preparation of 4-bromo-2,3',4',5'-tetrafluorobiphenyl A mixture of 28.0 g (93.0 mmol) of 3-fluoro-4-iodobromobenzene, 19.6 g (111 mmol) of 3,4,5-trifluorophenylboronic acid, 25.7 g (186 mmol) of potassium carbonate, 3.20 g (27.9 mmol) of tetrakis(triphenylphosphine) palladium, 200 ml of dimethoxyethane and 150 ml of water was heated and stirred at 70°C for 20 hrs. The reaction mixture was extracted with toluene, an organic layer was washed once with an aqueous solution of sodium bicarbonate and three times with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography (elude: heptane) and recrystallized (methanol) to isolate 7.0 g (22.9 mmol, 25% yield) of 4-bromo-2,3',4',5'-tetrafluorobiphenyl.

Reference： [1]Current Patent Assignee: CHISSO CORPORATION - EP1160251, 2001, A2

5
[ 79832-89-6 ]
[ 143418-49-9 ]
3',4',5'-trifluoro-4-(4-pentylcyclohexyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 631 - 636
[2]Journal of Organometallic Chemistry,2009,vol. 694,p. 2290 - 2294
[3]Applied Organometallic Chemistry,2013,vol. 27,p. 494 - 498

6
[ 121219-03-2 ]
[ 143418-49-9 ]
[ 335125-98-9 ]

Yield	Reaction Conditions	Operation in experiment
81.5%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 80℃; for 4h;Inert atmosphere;	Synthesis of Compound (S3-3) [0269] At first, 75.0 g of <strong>[121219-03-2]4-bromo-3-fluorophenol</strong> (S3-1), 82.9 g of 3,4,5-trifluorophenyl-boric acid (S3-2), 13.6 g of tetrakis(triphenylphosphine)palladium, 108.5 g of sodium carbonate and 1100 ml of a mixed solvent of dimethoxyethane/water=2/1 (volume ratio) were added into a reactor under nitrogen atmosphere, and the mixture was heated to 80 C. and stirred for 4 hr. Next, the reaction solution was cooled to room temperature, added with toluene and then washed with 1N hydrochloric acid and water. Afterwards, the solution was dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. Subsequently, the product was purified by silica-gel column chromatography with a mixed solvent of heptane/ethyl acetate=4/1 as the eluent and then dried under reduced pressure. The obtained residue was recrystallized in heptane to obtain 77.5 g of 3-fluoro-4-(3,4,5-trifluorophenyl)phenol (S3-3). The yield of (S3-3) from (S3-1) was 81.5%.
74%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In isopropyl alcohol; for 5h;Inert atmosphere; Reflux;	[Synthesis of the Compound (T-11)]; 4-Bromo-3-fluorophenol (T-10; 5.00 g), 3,4,5-trifluorophenylboronic acid (5.07 g), potassium carbonate (10. 9 g), Pd(Ph3P)2Cl2 (0.552 g), and 2-propanol were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 5 hours. The reaction mixture was cooled to 25 C, and then poured into water (100 ml) and toluene (100 ml) and mixed. Then, the mixture was allowed to stand to be separated into two layers of organic and aqueous layers, and the extraction to an organic layer was carried out. The obtained organic layer was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The obtained solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder. The product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11 and dried, whereby 4.79 g of 4-hydroxy-2,3',4',5'-tetrafluoro-1,1'-biphenyl (T-11) was obtained. The yield based on the compound (T-1) was 74%.

Reference： [1]Patent: US2013/85306,2013,A1 .Location in patent: Paragraph 0269
[2]Patent: EP2116522,2009,A1 .Location in patent: Page/Page column 55-56

7
[ 26156-48-9 ]
[ 143418-49-9 ]
[ 1251843-90-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In methanol; at 100℃; for 0.166667h;microwave irradiation;	Methyl 2-bromoisonicotinate (4 g, 18.52 mmol), 3,4,5-trifluorophenylboronic acid (4.89 g, 27.77 mmol), potassium carbonate (3.84 g, 27.77 mmol) and PdCl2 (dppf) (0.402 g, 0.56 mmol) were mixed in methanol (30 mL) in two separate 20 mL microwave vials. The vials were capped and heated at 100 C. for 10 min in a single node microwave reactor. Water and DCM were added and the phases were separated. The water phase (pH 9) was extracted with DCM and the combined organic phase washed with brine, passed through a phase separator and evaporated to yield a brown solid. The residue was dissolved in DCM and purified by SCX-2 cation exchange chromatography. Methyl 2-(3,4,5-trifluorophenyl)isonicotinate (2.62 g, 52%) was isolated as a slightly yellow solid. MS m/z 268 (M+H)+

Reference： [1]Patent: US2010/261755,2010,A1 .Location in patent: Page/Page column 27

8
[ 22348-32-9 ]
[ 143418-49-9 ]
[ 1260503-81-8 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 8624 - 8626
[2]Chemical Communications,2010,vol. 46,p. 8624 - 8626

9
[ 827-94-1 ]
[ 143418-49-9 ]
[ 1426332-54-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium phosphate tribasic heptahydrate; palladium diacetate In water; N,N-dimethyl-formamide at 80℃; for 0.333333h;

Reference： [1]Liu, Chun; Song, Xiaoxiao; Ni, Qijian; Qiu, Jieshan [ARKIVOC, 2012, vol. 2012, # 9, p. 62 - 75,14]

10
[ 128055-74-3 ]
[ 143418-49-9 ]
[ 1425942-31-9 ]

Reference： [1]Journal of Materials Chemistry C,2013,vol. 1,p. 2183 - 2192

11
[ 143418-49-9 ]
[ 615-36-1 ]
[ 915416-45-4 ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6566 - 6574
[2]Journal of the American Chemical Society,2013,vol. 135,p. 6618 - 6625

12
[ 84322-56-5 ]
[ 143418-49-9 ]
[ 1446789-32-7 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 7028 - 7032
Angew. Chem.,2013,vol. 125,p. 7166 - 7170,5

13
[ 84322-56-5 ]
[ 143418-49-9 ]
[ 1446789-24-7 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 7028 - 7032
Angew. Chem.,2013,vol. 125,p. 7166 - 7170,5

14
[ 392-57-4 ]
[ 143418-49-9 ]
[ 1446789-27-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate; XPhos In tetrahydrofuran; water; toluene at 95℃; for 14h; Inert atmosphere;

Reference： [1]Kniep, Florian; Jungbauer, Stefan H.; Zhang, Qi; Walter, Sebastian M.; Schindler, Severin; Schnapperelle, Ingo; Herdtweck, Eberhardt; Huber, Stefan M. [Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 7028 - 7032][Angew. Chem., 2013, vol. 125, # 27, p. 7166 - 7170,5]

15
[ 121848-75-7 ]
[ 143418-49-9 ]
[ 1505455-99-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; potassium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Reflux;

Reference： [1]Yu, Yue; Wu, Zhaoxin; Li, Zhanfeng; Jiao, Bo; Li, Lu; Ma, Lin; Wang, Dongdong; Zhou, Guijiang; Hou, Xun [Journal of Materials Chemistry C, 2013, vol. 1, # 48, p. 8117 - 8127]

16
[ 105931-73-5 ]
[ 143418-49-9 ]
[ 187804-77-9 ]

Yield	Reaction Conditions	Operation in experiment
36.8 g	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; potassium carbonate In toluene; butan-1-ol for 6h; Inert atmosphere; Reflux;	15.1 First step Into a reaction vessel under a nitrogen atmosphere, 50.0 g (166 mmol) of 4-bromo-2-fluoro-1-iodobenzene, 29.3 g (166 mmol) of (3,4,5-trifluorophenyl)boronic acid, 45.9 g (332 mmol) of potassium carbonate, 10.7 g (33.2 mmol) of tetrabutylammonium bromide (TBAB), 2.7 g (2.3 mmol) of tetrakis (triphenyl phosphine) palladium, 300 mL of toluene and 200 mL of 1-butanol were put, and the resultant mixture was subjected to heating reflux for 6 hours. A reaction liquid was poured into 300 mL of water, and then the resultant mixture was extracted with toluene, and the resultant extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. Then, an insoluble matter was separated by filtration and then a filtrate was concentrated under reduced pressure. A residue was purified according to fractionation by column chromatography using heptane as an eluent and silica gel as a filler, and thus 36.8 g of 4-bromo-2,3',4',5'-tetrafluoro-1,1'-biphenyl was obtained.
13.9 g	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 5h; Inert atmosphere; Reflux;	6 Preparation of the compound represented by formula (I-6) The compounds of the formula (I-6-1) A reaction vessel 10.0 g (0.0569 mol), formula (I-6-2) with the compound represented by 17.1 g (0.0569 mol), potassium carbonate 11.8g (0.0853 mol) was added tetrahydrofuran 100mL, the water 100mL. Tetrakis (triphenylphosphine) palladium(0) 0.66 g (0.569 mmol) was added after the inside of the system was replaced with nitrogen,and heated to reflux for 5 hours. Diluted with toluene, washed with water, brine, and purified bycolumn chromatography (silica gel) to give the formula (the I-6-3) with the compoundrepresented by 13.9 g (0.0455 mol).

Reference： [1]Current Patent Assignee: CHISSO CORPORATION - EP2690103, 2014, A1 Location in patent: Paragraph 0286
[2]Current Patent Assignee: DIC CORP. - JP2015/110532, 2015, A Location in patent: Paragraph 0144-0145

17
[ 50670-58-1 ]
[ 143418-49-9 ]
[ 1608121-92-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux;	General procedure: To a solution of bromobiphenyl aldehyde 11 (390 mg, 1.5 mmol) and 4-fluoro phenyl boronic acid 12a (209.8 mg, 1.5 mmol) in 2 M aqueous sodium carbonate (2 mL) and toluene/ethanol (12:4 mL) is added a catalytic amount (0.4 mol %) of tetrakis-triphenylphosphine palladium, and the mixture was heated to reflux under argon atmosphere for 3-4 h. After completion of the reaction, the reaction mixture is cooled to room temperature and extracted with ethyl acetate (3 x 30 mL) and the organic phase was extracted with water and brine solution, dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to get the crude product. This crude product was further purified by column chromatography (10% ethyl acetate and hexane) to afford the pure terphenyl aldehydes (13a) as a white solid in 310 mg, 74% yield; mp: 135-136 C; 1H NMR (300 MHz, CDCl3): δ 7.12-7.19 (m, 2H), 7.57-7.73 (m, 6H), 7.78 (d, 2H, J = 8.3 Hz), 7.96 (d, 2H, J = 8.3 Hz), 10.06 (s, 1H); (ESI) MS: m/z 277 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2714 - 2723

18
[ 1260685-63-9 ]
[ 143418-49-9 ]
C₆₀H₈₈BrF₃N₂O₂S₂ [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 9939 - 9942

19
[ 452-79-9 ]
[ 143418-49-9 ]
4-(3,4,5-trifluorophenyl)-3-fluorotoluene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.5 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; at 100℃; under 18751.9 Torr; for 17h;Autoclave;	[0168] (13-2) A solution prepared by suspending 3-fluoro- 4-iodotoluene (12.0 g) produced in 13-1, 3,4,5-trifluorophe- nylboric acid (9.0 g), anhydrous potassium carbonate (4.1 g), and tetrakis-triphenylphosphine palladium(0) (0.33 g) in ethanol (60 mE) was heated to 1000 C. (2.5 MPa) in an autoclave and then stirred for 17 hours. Afier the solution was allowed to cool to room temperature, toluene and water were added to separate an organic layet The organic layer was washed with saturated brine and then dried with sodium sulfate. The sodium sulfate was filtered off, and the organic solvent was distilled off under reduced pressure. Then, the residue was purified by silica gel column chromatography to yield 9.5 g of 4-(3,4,5-trifluorophenyl)-3-fluorotoluene as a colorless solid.

Reference： [1]Patent: US2014/275577,2014,A1 .Location in patent: Paragraph 0166; 0168

20
[ 119-30-2 ]
[ 143418-49-9 ]
[ 1258622-02-4 ]

Reference： [1]ACS Combinatorial Science,2015,vol. 17,p. 32 - 38

21
[ 77-85-0 ]
[ 2052-49-5 ]
[ 143418-49-9 ]
tetrabutylammonium 4-methyl-1-(3,4,5-trifluorophenyl)-2,6,7-trioxa-1-borabicyclo[2.2.2]octan-1-uide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	In water at 20℃;	Tetrabutylammonium Aryltriolborates 4; General Procedure General procedure: To a round-bottom flask (25 mL), an arylboronic acid (2 mmol), 1,1,1-tris(hydroxymethyl)ethane (1; 0.240 g, 2 mmol), and n-Bu4NOH (25 wt% in H2O; 6.228 g, 6 mmol) were added. After being stirred at r.t. overnight, the reaction mixture was extracted with CH2Cl2 (3 × 10 mL). The combined extract was dried over anhyd MgSO4, concentrated, and dried in vacuo to give the almost pure product 4, which was further purified by crystallization if appropriate.

Reference： [1]Huang, Wenhua; Zhao, Shuang-Hong; Xu, Ning [Synthesis, 2015, vol. 47, # 3, p. 359 - 366]

22
[ 143418-49-9 ]
[ 4373-60-8 ]
2-(3',4'-difluoro-[1,1'-biphenyl]-3-yl)pyridine [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 7783 - 7790

23
C₂₄H₂₇BrIN₃O₃ [ No CAS ]
[ 143418-49-9 ]
[ 240139-82-6 ]
C₃₆H₃₁F₆N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₂₄H₂₇BrIN₃O₃; [2-methoxy-5-(trifluoromethyl)phenyl]boronic acid With bis-triphenylphosphine-palladium(II) chloride; water; sodium hydrogencarbonate In 1,2-dimethoxyethane at 90℃; Stage #2: 3,4,5-trifluorophenylboronic acid With bis-triphenylphosphine-palladium(II) chloride; water; sodium hydrogencarbonate In 1,2-dimethoxyethane at 90℃;

Reference： [1]Lin, Songnian; Zhang, Fengqi; Jiang, Guoqiang; Qureshi, Sajjad A.; Yang, Xiaodong; Chicchi, Gary G.; Tota, Laurie; Bansal, Alka; Brady, Edward; Trujillo, Maria; Salituro, Gino; Miller, Corey; Tata, James R.; Zhang, Bei B.; Parmee, Emma R. [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 19, p. 4143 - 4147]

24
[ 3842-55-5 ]
[ 143418-49-9 ]
2, 4-diphenyl-6-(3,4,5-trifluorophenyl)-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 2-chloro-4,6-diphenyl-1,3,5-triazine; 3,4,5-trifluorophenylboronic acid With potassium carbonate In tetrahydrofuran; water at 20℃; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; water for 12h; Reflux;	1.1 (1) Compound a Synthesis 7.61 g (0.0284 mol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 5 g (0.0284 mol) of 3,4,5-trifluorophenylboronic acid and K2CO3 11.79 g (0.0853 mol) THF under nitrogen atmosphere The mixture was added to (tetrahydrofuran) / H 2 O (3: 1) solvent and stirred at room temperature for 20 to 30 minutes. 1.64 g (0.00142 mol) of Pd (PPh3) 4 (Tetrakis (triphenylphosphine) palladium (0)) was further added, followed by stirring under reflux for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and filtered using distilled water, acetone, and ethyl acetate.Drying to a yellow solid afforded 9.68 g beige solid (Compound a) (yield: 94%).
83%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;	(Synthesis of Intermediate A1) In a 50 mL eggplant flask under a nitrogen atmosphere, 2-chloro-4,6-diphenyl-1,3,5-triazine (803 mg), 3,4,5-trifluorophenylboronic acid (528 mg), potassium carbonate (1. 24 g) and tetrakistriphenylphosphine palladium (174 mg) were added, and THF (22 mL) and water (7 mL) were added to dissolve the mixture. The reaction mixture was degassed and heated to reflux for 24 hours. The reaction mixture was allowed to cool, and ethyl acetate (15 mL) and water (15 mL) were added. The insoluble material was collected by filtration and washed with ethyl acetate and acetone to obtain Intermediate A1 (902 mg, yield 83%).
77%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 106℃; for 12h; Inert atmosphere;

	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; trifluoroacetic acid
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2019/63922, 2019, A Location in patent: Paragraph 0144-0147
[2]Current Patent Assignee: TOYOBO CO LTD - JP2021/172629, 2021, A Location in patent: Paragraph 0126-0127
[3]Li, Yun; Liang, Jiao-Jiao; Li, Hong-Cheng; Cui, Lin-Song; Fung, Man-Keung; Barlow, Stephen; Marder, Seth R.; Adachi, Chihaya; Jiang, Zuo-Quan; Liao, Liang-Sheng [Journal of Materials Chemistry C, 2018, vol. 6, # 20, p. 5536 - 5541]
[4]Lee, Dong Ryun; Kim, Mounggon; Jeon, Sang Kyu; Hwang, Seok-Ho; Lee, Chil Won; Lee, Jun Yeob [Advanced Materials, 2015, vol. 27, # 39, p. 5861 - 5867]
[5]Jang, Ji Seon; Han, Si Hyun; Choi, Hye Won; Yook, Kyoung Soo; Lee, Jun Yeob [Organic electronics, 2018, vol. 59, p. 236 - 242]

25
[ 90905-31-0 ]
[ 143418-49-9 ]
2-(3,4,5-trifluorophenyl)pyrimidine-5-carbaldehyde [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7426 - 7432

26
[ 709665-73-6 ]
[ 143418-49-9 ]
methyl 2-((tert-butoxycarbonyl)amino)-2-(3',4',5'-trifluoro-[1,1'-biphenyl]-4-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; water; at 100.0℃; for 2.0h;Microwave irradiation; Inert atmosphere; Sealed tube;	General procedure: Aryl bromide (0.20g) and the appropriate boronic acid or boronate ester (1.5 eq) were dispersed in degassed THF (3mL) and degassed 1M Na2CO3(aq) (1mL) in a 10mL microwave vessel. A steady stream of nitrogen was bubbled through the mixture for 5min, before adding PdCl2(PPh3)2 (41mg, 0.1 eq), then immediately sealing the tube. The mixture was heated at 100C in an aluminium heating block for 2h, at which point LC-MS analysis indicated the reaction was complete. After cooling, the mixture was diluted with EtOAc (10mL) and water (10mL), and the aqueous layer discarded. The organic layer was filtered through a plug of cotton wool, before concentration and further purification by FCC (eluent DCM or MeOH/DCM 0:100 to 5:95 for more polar compounds).

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 110,p. 43 - 64

27
[ 14508-49-7 ]
[ 143418-49-9 ]
C₁₀H₅F₃N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With O₄P^(3-)3K⁽¹⁺⁾5H₂O; tris(1-adamantyl)phosphine; C₂₈H₂₆N₂O₈Pd₂S₂ In tetrahydrofuran at 70℃; for 5h; Inert atmosphere; Schlenk technique;
73%	With O₄P^(3-)3K⁽¹⁺⁾5H₂O; tris(1-adamantyl)phosphine; {2-[((acetyl-κO)amino)phenyl-κC](tri-1-adamantylphosphine)palladium}(p-toluenesulfonate) In tetrahydrofuran at 70℃; for 5h;	To a mixture of 2-chioropyrazine (44 tL, 0.50 mmol, 1 equiv), 3,4,5-trifluorophenyl- boronic acid (132 mg, 0.75 mmol, 1.5 equiv), and K3P045H20 (0.45 g, 1.5 mmol, 3 equiv) was added THF (400 jtL) then a THF stock solution of 3 and PAd3 (100 jiL, 0.25 imol of Pd/PAd3).The mixture was stirred at 70 °C for 5 h. The reaction mixture was diluted with ethyl acetate then extracted with water. The combine organic layers were evaporated and the crude product was purified by flash chromatography. After drying, 77 mg (73 %) of 31 was obtained as a white solid.‘H NMR (501 MHz, CDCI3) ö 8.98 (d, J 1.6 Hz, 1H), 8.66 - 8.62 (m, 1H), 8.57 (d, J- 2.5 Hz,1H), 7.75-7.65 (m, 2H).13C{’H} NMR (126 MHz, CDC13) ö 151.7 (ddd, J 250.7, 10.2, 4.0 Hz), 149.4 (dt, J= 1.3, 2.5Hz), 144.3,144.0,141.6, 140.9(dt,J=255.8, 15.4Hz), 132.3 (dt,J5.0,7.6 Hz), 11l.0(dd,J 17.1, 5.5 Hz).HRMS (ESI) mlz calculated for C10H5F3N2 (M+1) 211.0478, found 211.0471.

Reference： [1]Chen, Liye; Ren, Peng; Carrow, Brad P. [Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6392 - 6395]
[2]Current Patent Assignee: PRINCETON UNIVERSITY - WO2017/75581, 2017, A1 Location in patent: Page/Page column 27

28
[ 1133-80-8 ]
[ 143418-49-9 ]
[ 1962986-14-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With C₃₅H₄₀N₄O₉⁽²⁺⁾*2Cl^(1-); palladium diacetate; potassium hydroxide In ethanol at 100℃; for 1.5h; Green chemistry;
98%	With potassium <i>tert</i>-butylate In ethanol; water Reflux;
97%	With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;

97%	With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium <i>tert</i>-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Inert atmosphere;	Typical procedure for Suzuki-Miyaura reaction General procedure: The appropriate amounts of PdCl2, Glu-IMSs, and t-BuOK were added to THF under N2 atmosphere. The mixture was stirred at 60 oC for 10 min, remove the solvent, then aryl halide (1.0 mmol), aryl boronic acid (1.5 mmol), K2CO3 (2.0 mmol) and water (3.0 mL) were added. The mixture was heated to appropriate temperature under N2 atmosphere. The conversion and yield was monitored by GC-MS analysis
97%	With C₃₂H₃₉Br₂N₃O₁₀Pd; potassium carbonate In ethanol; water at 90℃; for 0.5h; Inert atmosphere;	4.6 General procedure for the Suzuki reaction catalyzed by Glu-NHCs-Pd(II)-PEPPSI complexes 2a-d General procedure: Degassed EtOH/H2O (v/v = 3:1, 3.0mL) was transfer to a flask with the corresponding amount of K2CO3(2.0mmol), Glu-NHCs-Pd(II)-PEPPSI complex (0.01mol%), then stirred for about 5 min under N2 atmosphere, 4-bromotoluene (1.0mmol), phenylboronic acid (1.5mmol) was sequentially added, the reaction solution was kept at 90°C and stirred for the corresponding time shown in Tables 1, 2 and Fig.2. The mixture was diluted with 3.0mL of dichloromethane, and then washed with brine. The organic layer was collected and dried over MgSO4. The organic solventwas concentrated in vacuum, and the product was purifiedby flash chromatograph.
96%	With potassium phosphate heptahydrate; [1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-n-hexadecylimidazole-2-ylidene]Pd(pyridine)Br₂ In ethanol; water at 60℃; for 1h; Inert atmosphere; Green chemistry;	4.6. Typical procedures for Suzuki-Miyaura reactions General procedure: Appropriate amounts of Carb-NHC-Pd complexes, and K3PO37H2O(2.0 mmol) were added to degassed EtOH/H2O (v/v = 3:1, 3.0 mL)under N2 atmosphere. Then, aryl halide (1.0 mmol) and aryl boronicacid (1.25 mmol) were added and the solution was kept at a certaintemperature with stirred for the corresponding time. The conversion andyield were determined by gas chromatography-mass spectrometryanalysis with n-dodecane as internal standard (See SI for detailed parameters).The mixture was diluted using 20 mL of ethyl acetate, andthen washed with 10 mL of brine three times. The resultant organic layerwas collected and dried with dry MgSO4. The organic layer wasconcentrated under vacuum, and purified by flash chromatograph (petroleumether/ethyl acetate, 30:1 to 20:1).
98 %	With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-benzylbenzimidazolinium bromine salt; palladium diacetate; potassium carbonate In ethanol; water Reflux;	General procedure for Pd/Glc-BzIm ILs-catalyzed Suzuki reactions General procedure: In air, the appropriate amounts of Glc-BzIm ILs, Pd source and base wereadded to a dry Schlenk tube, then evacuated and refilled three to five timeswith nitrogen. Fresh distilled 1,4-dioxane was added and the mixture wasthen stirred for about 30 min at 80 C to generate catalytic species. Finally,the 1,4-dioxane was evaporated, then arylboronic acid, aryl halide, requiredsolvent and internal standard decane were sequentially added. The courseof Suzuki reaction was monitored by gas chromatography-mass spectrometry.After the reaction completed, the substrate was extracted with ethylacetate, purified by column chromatography (HE/EA 30/1 to 5/1).

Reference： [1]Zhou, Zhonggao; Yuan, Yangyang; Xie, Yongrong; Li, Mei [Catalysis Letters, 2018, vol. 148, # 9, p. 2696 - 2702]
[2]Zhou, Zhonggao; Li, Mei; Liu, Guangsheng; Xu, Guohai; Xue, Jun [Applied Organometallic Chemistry, 2019, vol. 33, # 7]
[3]Zhou, Zhonggao; Zhao, Yan; Zhen, Hongyu; Lin, Zhenghuan; Ling, Qidan [Applied Organometallic Chemistry, 2016, vol. 30, # 11, p. 924 - 931]
[4]Du, Ziyi; Lu, Dongliang; Pan, Yan; Xie, Qian; Xue, Jun; Yuan, Yangyang; Zhou, Xin; Zhou, Zhonggao [Carbohydrate Research, 2020, vol. 496]
[5]Zhou, Zhonggao; Xie, Qian; Li, Jing; Yuan, Yangyang; Liu, Yong; Liu, Yulong; Lu, Dongliang; Xie, Yongrong [Catalysis Letters, 2022, vol. 152, # 3, p. 838 - 847]
[6]Xie, Qian; Li, Jing; Wen, Xiaoming; Huang, Yanxia; Hu, Yunchi; Huang, Qing; Xu, Guohai; Xie, Yongrong; Zhou, Zhonggao [Carbohydrate Research, 2022, vol. 512]
[7]Wen, Xiaoming; Wang, Jian; He, Luan; Wei, Bisheng; Xie, Ying [Journal of Carbohydrate Chemistry, 2022, vol. 41, # 6, p. 369 - 384]

29
[ 16433-88-8 ]
[ 143418-49-9 ]
[ 1962986-20-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;
96%	With potassium <i>tert</i>-butylate In ethanol; water Reflux;
96%	With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium <i>tert</i>-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Inert atmosphere;	Typical procedure for Suzuki-Miyaura reaction General procedure: The appropriate amounts of PdCl2, Glu-IMSs, and t-BuOK were added to THF under N2 atmosphere. The mixture was stirred at 60 oC for 10 min, remove the solvent, then aryl halide (1.0 mmol), aryl boronic acid (1.5 mmol), K2CO3 (2.0 mmol) and water (3.0 mL) were added. The mixture was heated to appropriate temperature under N2 atmosphere. The conversion and yield was monitored by GC-MS analysis

96%	With C₃₂H₃₉Br₂N₃O₁₀Pd; potassium carbonate In ethanol; water at 90℃; for 0.5h; Inert atmosphere;	4.6 General procedure for the Suzuki reaction catalyzed by Glu-NHCs-Pd(II)-PEPPSI complexes 2a-d General procedure: Degassed EtOH/H2O (v/v = 3:1, 3.0mL) was transfer to a flask with the corresponding amount of K2CO3(2.0mmol), Glu-NHCs-Pd(II)-PEPPSI complex (0.01mol%), then stirred for about 5 min under N2 atmosphere, 4-bromotoluene (1.0mmol), phenylboronic acid (1.5mmol) was sequentially added, the reaction solution was kept at 90°C and stirred for the corresponding time shown in Tables 1, 2 and Fig.2. The mixture was diluted with 3.0mL of dichloromethane, and then washed with brine. The organic layer was collected and dried over MgSO4. The organic solventwas concentrated in vacuum, and the product was purifiedby flash chromatograph.
97 %	With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-benzylbenzimidazolinium bromine salt; palladium diacetate; potassium carbonate In ethanol; water Reflux;	General procedure for Pd/Glc-BzIm ILs-catalyzed Suzuki reactions General procedure: In air, the appropriate amounts of Glc-BzIm ILs, Pd source and base wereadded to a dry Schlenk tube, then evacuated and refilled three to five timeswith nitrogen. Fresh distilled 1,4-dioxane was added and the mixture wasthen stirred for about 30 min at 80 C to generate catalytic species. Finally,the 1,4-dioxane was evaporated, then arylboronic acid, aryl halide, requiredsolvent and internal standard decane were sequentially added. The courseof Suzuki reaction was monitored by gas chromatography-mass spectrometry.After the reaction completed, the substrate was extracted with ethylacetate, purified by column chromatography (HE/EA 30/1 to 5/1).

Reference： [1]Zhou, Zhonggao; Zhao, Yan; Zhen, Hongyu; Lin, Zhenghuan; Ling, Qidan [Applied Organometallic Chemistry, 2016, vol. 30, # 11, p. 924 - 931]
[2]Zhou, Zhonggao; Li, Mei; Liu, Guangsheng; Xu, Guohai; Xue, Jun [Applied Organometallic Chemistry, 2019, vol. 33, # 7]
[3]Du, Ziyi; Lu, Dongliang; Pan, Yan; Xie, Qian; Xue, Jun; Yuan, Yangyang; Zhou, Xin; Zhou, Zhonggao [Carbohydrate Research, 2020, vol. 496]
[4]Zhou, Zhonggao; Xie, Qian; Li, Jing; Yuan, Yangyang; Liu, Yong; Liu, Yulong; Lu, Dongliang; Xie, Yongrong [Catalysis Letters, 2022, vol. 152, # 3, p. 838 - 847]
[5]Wen, Xiaoming; Wang, Jian; He, Luan; Wei, Bisheng; Xie, Ying [Journal of Carbohydrate Chemistry, 2022, vol. 41, # 6, p. 369 - 384]

30
[ 458-50-4 ]
[ 143418-49-9 ]
C₁₃H₈F₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrabutylammomium bromide; potassium carbonate; In water; isopropyl alcohol; toluene; for 6h;Reflux;	A mixture of 3,4,5-trifluorophenylboronic acid (47.187 g, 0.268 mol), <strong>[458-50-4]1-bromo-2-fluoro-4-methoxybenzene</strong> (50 g, 0.244 mol), TBAB (19.654 g, 0.0610 mol), potassium carbonate (67.410 g, 0.488 mol), 2-propanol (210 mL), toluene (210 mL) and water (60 mL) was heated and refluxed for 6 hours. The reaction mixture was poured into water (300 mL), and subjected to extraction with toluene (200 mL×3). The extract was washed with saturated brine (50 mL×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (heptane) to obtain compound (236-a) (50 g; 80percent) as a colorless crystal.

Reference： [1]Patent: US2016/280996,2016,A1 .Location in patent: Paragraph 0159

31
[ 254-60-4 ]
[ 143418-49-9 ]
C₆H₄BF₃O₂*C₈H₆N₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 2710 - 2727

32
[ 1124382-72-4 ]
[ 143418-49-9 ]
8-(3,4,5-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 2h;	a) 8-(3,4,5-Trifluorophenyl)-ri,2,41triazolori,5-alpyridin-2-amine In a 150 ml round-bottomed flask were combined 8-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-amine (1.5 g, 7.04 mmol), (3,4,5-trifluorophenyl)boronic acid (1.24 g, 7.04 mmol) and cesium carbonate (4.59 g, 14.1 mmol). The mixture was dissolved in dioxane (60 ml) and water (6 ml). l, -Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (515 mg, 704 mupiiotaomicron) was added and the mixture was stirred for 2 hours at 100C. Chromatography (silica gel, 50 g, ethyl acetate/heptane = 40:60 to 100:0) yielded the title compound as off-white solid (1.2 g, 58%). MS: m/z = 265.2 [M+H]+.
45%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 110℃; for 12h;Inert atmosphere;	General procedure: A mixture of <strong>[1124382-72-4]8-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine</strong> (35a) (10 g, 45 mmol), 4-fluoro-phenylboronic acid (12.61 g, 89 mmol), [1,1?-bis(diphenylphosphino)ferrocene] dichloro palladium(II) (2.93 g, 4 mmol) and sodium carbonate solution (2N in water, 44.6 mL, 89 mmol) in 1,4-dioxane (200 mL) was stirred at 110C under nitrogen atmosphere for 12h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The remainder was purified by preparative MPLC (silica gel, PE/ethyl acetate 20:1) to afford the product .

Reference： [1]Patent: WO2017/42114,2017,A1 .Location in patent: Page/Page column 62; 63
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3227 - 3241

33
[ 143418-49-9 ]
[ 151767-02-1 ]
C₄₁H₃₈F₃NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With O4P(3-)3K(1+)5H2O; tris(1-adamantyl)phosphine; {2-[((acetyl-kappaO)amino)phenyl-kappaC](tri-1-adamantylphosphine)palladium}(p-toluenesulfonate); In tetrahydrofuran; at 100℃; for 5h;Inert atmosphere;	To a mixture of montelukast sodium salt (152 mg, 0.25 mmol, 1 equiv), 3,4,5- trifluorophenyl boronic acid (53 mg, 0.30 mmol, 1.2 equiv), and K3P045 H20 (0.18 g, 0.60 mmol, 2.4 equiv) was added THF (2 mL) then a THF stock solution of 3 and PAd3 (1 mL, 2.5jtmol of Pd/PAd3). The mixture was stirred at 100 C for 5 h. The reaction mixture was diluted with ethyl acetate then extracted with saturated ammonium chloride then water. The combine organic layers were evaporated and the crude product was purified by flash chromatography. After drying, 152 mg (89 %) of 14 was obtained as yellow solid.H NMR (500 MHz, CDC13) 6 8.18 (d, J 1.8 Hz, 1H), 8.10 (d, J 8.5 Hz, 1H), 7.82 (d, J 8.4Hz, 1H), 7.74 (d, J- 1.9 Hz, 1H), 7.67 (d, J 8.6 Hz, 1H), 7.62 (dd, J- 5.0, 1.8 Hz, 1H), 7.59(d, J= 17.1 Hz, 1H), 7.48 (d, J= 17.1 Hz, TH), 7.40 (m, 1H), 7.37-7.28 (m, 5H), 7.18 -7.13(m, 2H), 7.10 (ddd, J= 7.6, 5.8, 3.0 Hz, 1H),5.29 (s, 1H),4.01 (t, J 7.2 Hz, 1H), 3.17 (ddd, J13.5, 11.2, 5.1 Hz, 1H), 2.90 (ddd, J- 13.5, 11.2, 5.4 Hz, 1H), 2.65 (d, J= 13.1 Hz, 1H), 2.57 (d,J= 16.2 Hz, 1H), 2.45 (d, J= 13.1 Hz, 1H), 2.38 (d, J= 16.1 Hz, 111), 2.28-2.09 (m, 2H), 1.60(d, J 4.9 Hz, 6H), 0.71 - 0.24 (m, 4H).C{H} NMR (126 MHz, CDC13) 176.3, 156.9, 151.5 (ddd, J= 249.9, 10.0, 4.2 Hz), 147.7,145.2, 143.6, 140.2, 139.7 (dt, J= 253.3, 15.4 Hz),139.4, 136.5, 136.4, 136.3 (m), 135.4, 131.5,129.0, 128.6, 128.5, 128.4, 127.1, 126.9, 126.5, 126.5, 126.4, 125.6, 125.4, 125.0, 119.4, 111.4(dd, J 12.6, 5.0 Hz), 73.8, 50.3, 40.3, 40.0, 38.9, 32.3, 31.8, 16.8, 12.7, 12,4.HRMS (ESI) m/z calculated for C41H38F3N03S (M+1) 682.2597, found 682.2598.

Reference： [1]Patent: WO2017/75581,2017,A1 .Location in patent: Page/Page column 18; 19

34
[ 1127-76-0 ]
[ 143418-49-9 ]
C₁₈H₁₃F₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 7709 - 7712

35
[ 4707-23-7 ]
[ 143418-49-9 ]
C₁₄H₅F₇O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene for 3h; Reflux;	3.1 According to the flow chart of the preparation method shown in Fig. 1, the coupling step S1100 is first carried out: 1eq reactants 1-a-1 and 1.1eq reactants 1-b-1 are dissolved in a solvent, 1.5 eq sodium bicarbonate, (Triphenylphosphine) palladium was added under the protection, and the mixture was heated to reflux for 3 hours and then dropped to room temperature. After extraction, the compound 2-a-1 was obtained by silica gel column. The solvent was a mixed solvent of toluene, ethanol and water , The volume of toluene, ethanol and water is chosen to be 4: 3: 3, and the total volume thereof is adjusted according to the amount of the reactants 1-a-1. Generally, 1 g of the reactants 1-a-1 correspond to 10 ml of the solvent, (Triphenylphosphine) palladium, preferably toluene as the extractant, and the silica gel column is preferably toluene. The resulting 2-a-1 is a white solid with a yield of 90% and a gas chromatographic purity of 98.2%.

Reference： [1]Current Patent Assignee: BEIJING SINEVA TECHNOLOGY CO LTD - CN106146251, 2016, A Location in patent: Paragraph 0111; 0112

36
[ 1559-88-2 ]
[ 143418-49-9 ]
2,3,3′,4′,5,5′,6-heptafluoro-1,1′-biphenyl [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 13188 - 13203

37
[ 143418-49-9 ]
[ 176317-02-5 ]
2,3,3′,4,4′,5′-hexafluoro-1,1′-biphenyl [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 13188 - 13203

38
[ 114744-50-2 ]
[ 143418-49-9 ]
5-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.9%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere;	5-Bromo-1,2,3,4-tetrahydroquinoline (300.0 mg, 1.4 mmol), (3,4,5- trifluorophenyl)boronic acid (248.0 mg, 1.4 mmol), Pd(dppf)C12 (103.0 mg, 141 imol), and cesium carbonate (919.0 mg, 2.8 mmol) were added to a mixture of dioxane (20.0 mL) andwater (2.0 mL). The reaction mixture was evacuated and refilled with nitrogen three times before being stirred at 100 C for 12 h. LCMS indicated 53% of the desired product was formed. The reaction mixture was concentrated in vacuo to give a residue that was purified by silica gel chromatography (eluting with petroleum ether/ethyl acetate). Concentration in vacuo led to 5 -(3 ,4,5-trifluorophenyl)- 1 ,2,3,4-tetrahydroquinoline (200.0 mg, 53.9% yield) as ayellow solid.

Reference： [1]Patent: WO2018/81091,2018,A1 .Location in patent: Paragraph 0215

39
[ 1000623-95-9 ]
[ 143418-49-9 ]
C₃₆H₄₀BrF₃N₂O₂S₂ [ No CAS ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 11854 - 11861

40
[ 61326-44-1 ]
[ 143418-49-9 ]
C₅₀H₂₄F₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.02%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 100℃; for 27h;Inert atmosphere;	Under argon protection,Tetrakis(4-bromophenyl)ethene 210.7 mg, 0.33 mmol) was added to the reaction flask in that order.3,4,5-trifluorobenzeneboronic acid (274.9 mg, 1.56 mmol),Potassium carbonate (135.4 mg, 0.98 mmol),Tetrakis(triphenylphosphine)palladium (20.3 mg, 0.018 mmol),Tetrabutylammonium bromide (12.3 mg, 0.038 mmol),Add 20 mL of toluene and 5 mL of deionized water.The mixture was heated to 100 ° C, reacted for 27 h, and the reaction was monitored by thin layer chromatography.After the system was lowered to 27 ° C, the liquid was separated.The aqueous phase was extracted with dichloromethane (15 mL×3) and the organic phases were combined.Add anhydrous sodium sulfate and filter,The filtrate is concentrated and subjected to thin layer chromatography.The developing agent ratio is dichloromethane: n-hexane (V: V) = 2:1,The bright blue band of the product (observed under a 365 nm UV lamp) is scraped off.After fully crushing, pour into a sand core funnel and rinse with 80 mL of dichloromethane.Evaporate dry solvent,Obtaining a yellow solid is the target product F-TPE,The weight was 169.2 mg, and the yield was 61.02percent.

Reference： [1]Patent: CN108947766,2018,A .Location in patent: Paragraph 0056; 0057; 0063; 0064; 0065; 0066

41
[ 143418-49-9 ]
[ 189367-54-2 ]
9,9-dihexyl-2,7-bis(3,4,5-trifluorophenyl)-9H-fluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride; In tetrahydrofuran; water; at 60 - 90℃; for 0.5h;Inert atmosphere;	General procedure: The appropriate amounts of PdCl2, Glu-IMSs, and t-BuOK were added to THF under N2 atmosphere. The mixture was stirred at 60 oC for 10 min, remove the solvent, then aryl halide (1.0 mmol), aryl boronic acid (1.5 mmol), K2CO3 (2.0 mmol) and water (3.0 mL) were added. The mixture was heated to appropriate temperature under N2 atmosphere. The conversion and yield was monitored by GC-MS analysis

Reference： [1]Carbohydrate Research,2020,vol. 496
[2]Applied Organometallic Chemistry,2019,vol. 33

42
[ 55583-59-0 ]
[ 143418-49-9 ]
4,6-bis(3,4,5-trifluorophenyl)pyrimidine-2,5-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 20h;Inert atmosphere; Reflux;	In the reaction vessel, <strong>[55583-59-0]4,6-dichloropyrimidine-2,5-diamine</strong>(344 mg, 1.92 mmol), 3,4,5-trifluorophenylboronic acid (0.778 g, 4.42 mmol),Ethanol in a solution of sodium carbonate (1.02 g, 9.61 mmol) and tetrakis (triphenylphosphine) palladium (0) (112 mg, 0.961 mmol) in toluene (19 mL)Add (5 mL) and distilled water (5 mL) at room temperature,After stirring for 20 hours under heating and reflux conditions under an argon atmosphere, the reaction solution was cooled to room temperature. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (10 mL). Thereafter, the whole organic layer was combined, saturated aqueous sodium chloride solution (10 mL) was added thereto, the mixture was stirred and washed, anhydrous sodium sulfate was added to the separated organic layer for dehydration, and the filtrate after filtration was concentrated under reduced pressure. The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4,6-Bis (3,4,5-trifluorophenyl) pyrimidine-2,5-diamine(0.640 g, 90% yield).

Reference： [1]Patent: JP2019/64981,2019,A .Location in patent: Paragraph 0098; 0099; 0100

43
[ 143418-49-9 ]
[ 915416-45-4 ]

Reference： [1]Patent: CN109761820,2019,A

44
[ 88-73-3 ]
[ 143418-49-9 ]
[ 915416-45-4 ]

Reference： [1]Patent: CN109942433,2019,A

45
[ 2923-18-4 ]
[ 143418-49-9 ]
[ 80172-04-9 ]

Reference： [1]Organic Process Research and Development,2019,vol. 23,p. 2345 - 2353

46
[ 765278-73-7 ]
[ 143418-49-9 ]
[ 2414570-36-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium diacetate; potassium carbonate; catacxium A In 1,2-dimethoxyethane; water at 100℃; for 18h; Inert atmosphere; Sealed tube;

Reference： [1]Meek, Simon J.; Zanghi, Joseph M. [Angewandte Chemie - International Edition, 2020, vol. 59, # 22, p. 8451 - 8455][Angew. Chem., 2020, vol. 132, # 22, p. 8529 - 8533,5]

47
[ 885267-41-4 ]
[ 143418-49-9 ]
5-(3,4,5-trifluorophenyl)quinoline-8-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrabutylammomium bromide; palladium diacetate; caesium carbonate In ethanol; water; toluene for 4h; Schlenk technique; Inert atmosphere; Reflux;

Reference： [1]Lyu, Xue-Li; Huang, Shi-Sheng; Huang, Yuan-Qiong; Li, Yong-Qiang; Song, Hong-Jian; Liu, Yu-Xiu; Wang, Qing-Min [Journal of Organic Chemistry, 2020, vol. 85, # 15, p. 10271 - 10282]

48
[ 552331-85-8 ]
1,2,4,6-tetra-O-acetyl-3-(4-bromo-1H-pyrazol-1-yl)-3-deoxy-beta-D-galactopyranoside [ No CAS ]
[ 143418-49-9 ]
5-bromopyridin-3-yl 3-deoxy-3-[4-(3,4,5-trifluorophenyl)-1H-pyrazol-1-yl]-1-thio-alpha-D-galactopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4%	Stage #1: 1,2,4,6-tetra-O-acetyl-3-(4-bromo-1H-pyrazol-1-yl)-3-deoxy-beta-D-galactopyranoside; 3,4,5-trifluorophenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 110℃; for 0.333333h; Microwave irradiation; Inert atmosphere; Stage #2: With phosphorus pentachloride; boron trifluoride diethyl etherate In dichloromethane at 20℃; for 3h; Stage #3: 5-bromopyridine-3-thiol Further stages;	5 5-Bromopyridin-3-yl 3-deoxy-3-[4-(3,4,5-trifluorophenyl)-1H-pyrazol-l-yl]-l- thio-alpha-D-galactopyranoside A nitrogen purged solution of 1,2,4,6-tetra- -acetyl-3-(4-bromo-1H-pyrazol- l -yl)- 3-deoxy-beta-D-galactopyranoside (250 mg, 0.52 mmol), (3,4,5-trifluorophenyl)boronic acid (184 mg, 1.05 mmol), K2CO3 (434 mg, 3.14 mmol) and Pd(dppf)Ch (58 mg, 0.079 mmol) in water/dioxane (1 :2, 4 mL) was heated 20 min at 110 °C in a microwave reactor. The mixture was partitioned between EtOAc and water and the organic phase was dried, evaporated and purified by chromatography (S1O2, PE/EtOAc). The obtained material and PCI5 (52 mg, 0.25 mmol) were dissolved in DCM (1.5 mL) and BF30Et2 (0.031 mL, 0.25 mmol) was added. The mixture was stirred 3 h at rt before it was diluted with DCM and washed with water and saturated aq NaHC03, dried and evaporated. The residue was dissolved with 5-bromopyridine-3-thiol (37 mg, 0.19 mmol) in DMF (1 mL). K2CO3 (53 mg, 0.39 mmol) was added and the mixture was stirred 18 h at rt. The mixture was diluted with EtOAc and washed with water and brine, the organic phase was dried and evaporated. The residue was stirred 1 h at rt in NaOMe (0.1 mL, 1M) and MeOH (1 mL). The reaction was quenched with acetic acid, concentrated and purified by prep HPLC (Cis, FhO/MeCN/0.1 % TFA) to afford the title compound (12 mg, 4 %). ESI-MS m/z calcd for [C2oHi7BrF3N304S] [M+H]+: 532.0; found: 531.7. NMR (400 MHz, Methanol-d4) d 8.68 (d, J = 1.7 Hz, 1H), 8.57 (d, J = 2.1Hz, 1H), 8.33 (t, J = 1.9 Hz, 1H), 8.19 (s, 1H), 7.92 (s, 1H), 7.37 (dd, J = 9.1, 6.5 Hz, 2H), 5.89 (d, J = 5.4 Hz, 1H), 4.90 - 4.86 (m, 1H), 4.59 (dd, J = 11.3, 2.7 Hz, 1H), 4.43 (t, J = 5.8 Hz, 1H), 4.19 (d, J = 2.1Hz, 1H), 3.74 - 3.67 (m, 2H).

Reference： [1]Current Patent Assignee: GALECTO BIOTECH AB - WO2021/1538, 2021, A1 Location in patent: Page/Page column 80-81

49
[ 1245748-53-1 ]
[ 143418-49-9 ]
[ 2624147-73-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In tetrahydrofuran at 85℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Christmann, Mathias; He, Guoli; List, Benjamin [Angewandte Chemie - International Edition, 2021, vol. 60, # 24, p. 13591 - 13596][Angew. Chem., 2021, vol. 133, # 24, p. 13703 - 13708,6]

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