[ CAS No. 501374-30-7 ] {[proInfo.proName]}

Name: 501374-30-7|5,5-Dimethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinane|98%
Brand: Ambeed
SKU: A1448954
Rating: 90 (28 reviews)

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2D 3D

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Quality Control of [ 501374-30-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 501374-30-7 ]

SDS Specification

Alternatived Products of [ 501374-30-7 ]

Product Details of [ 501374-30-7 ]

CAS No. :	501374-30-7	MDL No. :
Formula :	C₁₂H₁₄BF₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RHRLRPXJTDDILM-UHFFFAOYSA-N
M.W :	258.04	Pubchem ID :	11983971
Synonyms :

Calculated chemistry of [ 501374-30-7 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.78
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.75
Log Po/w (WLOGP) :	3.63
Log Po/w (MLOGP) :	2.42
Log Po/w (SILICOS-IT) :	2.56
Consensus Log Po/w :	2.47

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.92
Solubility :	0.0312 mg/ml ; 0.000121 mol/l
Class :	Soluble
Log S (Ali) :	-3.83
Solubility :	0.0381 mg/ml ; 0.000148 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.4
Solubility :	0.0102 mg/ml ; 0.0000396 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.77

Safety of [ 501374-30-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 501374-30-7 ]

* 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 [ 501374-30-7 ]

[ 501374-30-7 ] Synthesis Path-Downstream 1~88

1
[ 938-16-9 ]
[ 501374-30-7 ]
2,2-dimethyl-1-(4'-trifluoromethyl-biphenyl-2-yl)-propan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 1698 - 1699

2
[ 22526-24-5 ]
[ 501374-30-7 ]
2,2-dimethyl-1-(4'-trifluoromethyl-biphenyl-2-yl)-propan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 2706 - 2707

3
[ 826-73-3 ]
[ 501374-30-7 ]
4-(4-(trifluoromethyl)phenyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 5936 - 5945
[2]Organic Syntheses,2010,vol. 87,p. 209 - 217

4
[ 124-38-9 ]
[ 501374-30-7 ]
[ 455-24-3 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 8010 - 8013
[2]Angewandte Chemie - International Edition,2008,vol. 47,p. 5792 - 5795
[3]Green Chemistry,2013,vol. 15,p. 635 - 640
[4]Journal of the American Chemical Society,2006,vol. 128,p. 8706 - 8707
[5]Chemical Communications,2012,vol. 48,p. 6292 - 6294

5
[ 872094-27-4 ]
[ 501374-30-7 ]
(R)-(-)-11-acetoxy-2-(4-trifluoromethylphenyl)-10-methoxyapomorphine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 4077 - 4081

6
[ 579-74-8 ]
[ 501374-30-7 ]
[ 754-05-2 ]
1-[4'-trifluoromethyl-3-(2-trimethylsilanylethyl)biphenyl-2-yl]ethanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 16516 - 16517

7
[ 128796-39-4 ]
[ 126-30-7 ]
[ 501374-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium sulfate; In tetrahydrofuran; at 20℃;Inert atmosphere;	The dry THF (1 mL) solution of organoboronic acid (10 mmol), 2,2-dimethylpropan-1,3-diol (11 mmol, 1.2g), and MgSO4 (14 mmol, 1.7 g) mixture was stirred overnight at room temperature under Ar. The crude mixture was concentrated under a reduced pressure and neopentyl borate ester derivative (2) was purified on a silica gel column with yields varying in the range of 76-97% (hexane/ethyl acetate as the eluent).
	In diethyl ether; at 20℃;Inert atmosphere; Molecular sieve;	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]Journal of the American Chemical Society,2019,vol. 141,p. 4137 - 4146
[2]Organic Letters,2020,vol. 22,p. 2756 - 2760
[3]Chemical Communications,2012,vol. 48,p. 1538 - 1540
[4]Journal of Organic Chemistry,2017,vol. 82,p. 6503 - 6510
[5]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1527 - 1532
[6]Organic Letters,2014,vol. 16,p. 3200 - 3203
[7]Journal of the American Chemical Society,2014,vol. 136,p. 11224 - 11227
[8]Journal of the American Chemical Society,2021,vol. 143,p. 18617 - 18625
[9]Journal of the American Chemical Society,2020,vol. 142,p. 15454 - 15463
[10]Angewandte Chemie - International Edition,2019,vol. 58,p. 482 - 487
Angew. Chem.,2019,vol. 131,p. 492 - 497,6
[11]Organic Letters,2021,vol. 23
[12]Journal of the American Chemical Society,2007,vol. 129,p. 6098 - 6099
[13]Angewandte Chemie - International Edition,2008,vol. 47,p. 5792 - 5795
[14]Angewandte Chemie - International Edition,2008,vol. 47,p. 4866 - 4869
[15]Organic Letters,2009,vol. 11,p. 5426 - 5429
[16]Angewandte Chemie - International Edition,2010,vol. 49,p. 3371 - 3374
[17]Angewandte Chemie - International Edition,2011,vol. 50,p. 7022 - 7026
[18]Green Chemistry,2013,vol. 15,p. 635 - 640
[19]Journal of the American Chemical Society,2013,vol. 135,p. 3303 - 3306
[20]Chemistry - A European Journal,2013,vol. 19,p. 10378 - 10387
[21]Chemical Communications,2014,vol. 50,p. 8010 - 8013
[22]Organic Letters,2015,vol. 17,p. 4674 - 4677
[23]Organic Letters,2017,vol. 19,p. 794 - 797
[24]Organometallics,2017,vol. 36,p. 159 - 164
[25]Tetrahedron,2018,vol. 74,p. 3652 - 3662
[26]Chem,2019,vol. 5,p. 2718 - 2730

8
[ 941320-76-9 ]
[ 501374-30-7 ]
2,2-dimethyl-1-(4'-trifluoromethyl-biphenyl-2-yl)-propan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6098 - 6099

9
[ 916518-31-5 ]
[ 501374-30-7 ]
C₂₁H₂₁F₃N₂ [ No CAS ]
C₂₁H₂₁F₃N₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 14220 - 14221

10
1-phenyl-3-(triethylsilyl)prop-2-yn-1-one [ No CAS ]
[ 501374-30-7 ]
C₂₂H₂₅OSiF₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 3735 - 3737

11
[ 953813-08-6 ]
[ 501374-30-7 ]
C₁₅H₁₇F₃N₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 11750 - 11755

12
[ 501374-30-7 ]
C₁₇H₁₆F₃N [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 14220 - 14221

13
[ 93-04-9 ]
[ 501374-30-7 ]
[ 460743-71-9 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 4866 - 4869
[2]Organic Syntheses,2019,vol. 96,p. 36 - 52
[3]Journal of the American Chemical Society,2017,vol. 139,p. 10347 - 10358

14
[ 613-46-7 ]
[ 501374-30-7 ]
[ 460743-71-9 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3374 - 3377

15
[ 110590-81-3 ]
[ 501374-30-7 ]
[ 1192464-33-7 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 5426 - 5429

16
[ 201230-82-2 ]
[ 67-63-0 ]
[ 501374-30-7 ]
[ 444993-17-3 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 3371 - 3374

17
[ 1215180-93-0 ]
[ 501374-30-7 ]
[ 1095091-91-0 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 2438 - 2440

18
[ 98-86-2 ]
[ 501374-30-7 ]
[ 893739-29-2 ]
[ 1255789-60-6 ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 12975 - 12982
[2]Organic Letters,2010,vol. 12,p. 5318 - 5321
[3]Organic Letters,2010,vol. 12,p. 5318 - 5321

19
[ 501374-30-7 ]
[ 6185-76-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hexane / 3.5 h / 20 °C / Molecular sieve; Inert atmosphere; UV-irradiation 2: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C
	Multi-step reaction with 2 steps 1: hexane / 12 h / 20 °C / Molecular sieve; Inert atmosphere; UV-irradiation 2: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Ito, Kazuta; Tamashima, Hiroto; Iwasawa, Nobuharu; Kusama, Hiroyuki [Journal of the American Chemical Society, 2011, vol. 133, # 11, p. 3716 - 3719]
[2]Ito, Kazuta; Tamashima, Hiroto; Iwasawa, Nobuharu; Kusama, Hiroyuki [Journal of the American Chemical Society, 2011, vol. 133, # 11, p. 3716 - 3719]

20
[ 7228-47-9 ]
[ 501374-30-7 ]
[ 1188304-00-8 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7022 - 7026
[2]Chemical Communications,2012,vol. 48,p. 1538 - 1540

21
[ 89346-48-5 ]
[ 501374-30-7 ]
[ 1174895-53-4 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 19505 - 19511

22
[ 109384-19-2 ]
[ 501374-30-7 ]
[ 1191240-41-1 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 1538 - 1540

23
[ 455-18-5 ]
[ 201733-56-4 ]
[ 501374-30-7 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 115 - 118
[2]Journal of the American Chemical Society,2012,vol. 134,p. 115 - 118

24
[ 1354723-14-0 ]
[ 501374-30-7 ]
[ 1354723-38-8 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 816 - 819

25
[ 88132-08-5 ]
[ 501374-30-7 ]
[ 1286147-17-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); In toluene; at 125 - 135℃; for 1h;	This synthetic procedure is provided as a representative example for compounds shown in Table 3. A mixture of N,N-diethyl-2-(dimethylamino)benzamide (66 mg, 0.30 mmol), 2((4-trifluoromethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (81 mg, 0.32 mmol), RuH2(CO)(PPh3)3 (11 mg, 4 mol %) in toluene (0.4 mL) was heated at 125-135 C. (oil bath temperature) in a sealed vial for 1 h. The reaction progress was monitored by GC-MS analysis. The reaction mixture was cooled to RT and concentrated in vacuo. The residue was subjected to flash SiO2 column chromatography (eluent: EtOAc/hexanes). N,N-Diethyl-2-((4-trifluoromethyl)phenyl)benzamide (95 mg, 99% yield) was obtained as a light yellow solid. mp 81-82 C. (EtOAc/hexanes); IR (KBr) vmax 2977, 1628, 1430, 1326, 1290, 1165, 1125, 1109, 1069, 767 cm-1; 1H NMR (400 MHz, CDCl3) δ ppm: 7.68-7.57 (m, 4H), 7.51-7.33 (m, 4H), 3.83-3.62 (m, 1H), 3.13-2.83 (m, 2H) 2.77-2.58 (m, 1H), 0.88 (t, J=7.1 Hz, 3H), 0.78 (t, J=7.1 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ ppm: 169.99, 143.39, 136.88, 136.41, 129.70 (q, 2JC-F=32.7 Hz), 129.36, 129.20 (2C), 129.08, 128.32, 126.96, 125.17 (q, 3JC-F=3.7 Hz, 2C), 124.13 (q, 1JC-F=271.9 Hz), 42.29, 38.37, 13.42, 11.85. MS EI m/z (rel. int.) 321 (M+, 31), 320 (52), 249 (100), 201 (33), 152 (18); HRMS m/z (EI, M+) calcd for C18H18F3NO, 321.1340, found 321.1334.

Reference： [1]Patent: US2012/302752,2012,A1 .Location in patent: Page/Page column 17
[2]Organic Letters,2014,vol. 16,p. 3200 - 3203

26
[ 116-14-3 ]
[ 501374-30-7 ]
[ 92917-54-9 ]

Yield	Reaction Conditions	Operation in experiment
50%Spectr.	With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In tetrahydrofuran; tetrahydrofuran-d8; at 100℃; for 5h;Inert atmosphere;	Example 30 [0315] In a glove box, a THF (0.4 mL)-THF-D8 (0.1 mL) solution of Pd2(dba)3 (5 mg, 0.005 mmol), PCy3 (5.6 mg, 0.02 mmol), and 5,5-dimethyl-2-[4-(trifluoromethyl)phenyl]-1,3,2-dioxaborinane (25.8 mg, 0.1 mmol) was prepared in a pressure tube (capacity: 2 mL) under an inert atmosphere. α,α,α-Trifluorotoluene (12 μL, 0.097 mmol: internal standard for the 19F-NMR measurement) was added thereto. TFE (0.313 mmol: calculated from the container capacity described above and the applied pressure of 0.35 MPa) was further added thereto. This reaction solution was allowed to stand at 100 C. for 5 hours. The reaction was monitored by 19F-NMR. Based on the internal standard, it was confirmed that 1-(1,2,2-trifluoroethenyl)-4-(trifluoromethyl)benzene was obtained at a yield of 50%. RRN 90 1-(1,2,2-Trifluoroethenyl)-4-(trifluoromethyl)benzene [0316] 19F-NMR (THF-d8, δ/ppm): -179.8 (dd, JFF=32.8, 109.2 Hz, 1F), -115.0 (dd, JFF=65.5, 109.2 Hz, 1F), -100.8 (dd, JFF=32.6, 65.1 Hz, 1F), -65.5 (s,3F).
60%Spectr.		General procedure: The reactions were conducted with a pressure-tight NMR tube (Wilmad-LabGlass, 524-PV-7). To a solution of CuOtBu (2.7 mg, 0.02 mmol) and ligand in THF/THF-d8 (v/v’ = 4/1) (0.5 mL) was added arylboronic acids (0.022 mmol, 1.1 eq) and α,α,α-trifluorotoluene (2.4 L, 0.02 mmol; as an internal standard for 19F NMR). The resultant solution was transferred into the tube, and then TFE (3.5 atm, excess) was pressurized. After the reaction mixture was heated at 40 C for 24 h, Lewis acid (0.04 mmol, 2.0 eq) was added. Monitoring the reaction was performed by means of 19F NMR spectroscopy. The yields were determined by 19F NMR spectroscopy using α,α,α-trifluorotoluene as an internal standard.

Reference： [1]European Journal of Organic Chemistry,2013,p. 443 - 447
[2]Patent: US2013/324757,2013,A1 .Location in patent: Paragraph 0315-0316
[3]Chemistry Letters,2015,vol. 44,p. 1019 - 1021

27
[ 402-43-7 ]
[ 126-30-7 ]
[ 501374-30-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 9: Borylation with tetrakis - borylation of aryl bromides (Table 7)KOAc (1.84 g, 18.6 mmol, 3.0 eq.), neopentyl glycol (1.56 g, 15.0 mmol, 2.4 eq.) and tetrakis (1 .48 g, 7.50 mmol, 1 .2 eq.) were suspended in toluene (25 ml) and heated to 80C for 30 min. Afterwards a solution of the corresponding aryl bromide (see Table 7) and Pd-catalyst[Pd(PPh3)4 (144 mg, 0.125 mmol, 2 mol-%) or PdC (dppf) (102 mg, 0.125 mmol, 2 mol-%)] in toluene (5 ml) was added at 80C. The conversion of the reaction was followed by GC. The final product was identified by its mass using GC-MS-technology. Table 7: Examples of the borylation with tetrakis/neopentyl glycolTable 8: Retention times of aryl bromides and their borylation products

Reference： [1]Patent: WO2013/14579,2013,A1 .Location in patent: Page/Page column 11; 12; 13

28
[ 1426442-13-8 ]
[ 501374-30-7 ]
[ 1424035-53-9 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 3303 - 3306

29
[ 1025506-03-9 ]
[ 501374-30-7 ]
[ 1439838-66-0 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 5504 - 5506

30
[ 637-87-6 ]
[ 501374-30-7 ]
[ 146741-82-4 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3475 - 3479
Angew. Chem.,2014,vol. 126,p. 3543 - 3547,5

31
[ 608-28-6 ]
[ 501374-30-7 ]
2,6-dimethyl-4'-(trifluoromethyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3475 - 3479
Angew. Chem.,2014,vol. 126,p. 3543 - 3547,5

32
[ 1131-33-5 ]
[ 501374-30-7 ]
[ 1261465-23-9 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4292 - 4295

33
[ 694-59-7 ]
[ 501374-30-7 ]
[ 203065-88-7 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4292 - 4295

34
[ 73540-76-8 ]
[ 501374-30-7 ]
[ 1415045-39-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1527 - 1532

35
tris(4-trifluoromethylphenyl)antimony diacetate [ No CAS ]
[ 201733-56-4 ]
[ 501374-30-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; at 60℃; for 12h;	General procedure: A solution of triarylantimony diacetate (1: 0.5mmol), tetra(alkoxo)diboron (11: 1.5mmol), and dichlorobis(triphenylphosphine)palladium (II) (0.005mmol) in DME (5mL) was stirred at 60 C for 12h under air atmosphere. After dilution with CH2Cl2 (30mL) and water (20mL), the reaction mixture was separated and the aqueous layer was extracted with CH2Cl2 (30mL×2). The combined organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatograph on silica gel to give arylboronates (12, 14-23). The products were confirmed by comparison of NMR data and MS spectra with that in the literature.

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 765,p. 80 - 85

36
[ 51674-10-3 ]
[ 501374-30-7 ]
[ 1286147-17-8 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 11224 - 11227

37
[ 110-82-7 ]
[ 501374-30-7 ]
1-cyclohexyl-4-(trifluoromethyl)benzene [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 998 - 1001

38
C₁₇H₁₉BF₃O₂S^(1-)*Li⁽¹⁺⁾ [ No CAS ]
[ 98271-72-8 ]
[ 501374-30-7 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 2780 - 2783
Angew. Chem.,2015,vol. 127,p. 2820 - 2824,5

39
[ 1228374-02-4 ]
[ 201733-56-4 ]
[ 501374-30-7 ]

Yield	Reaction Conditions	Operation in experiment
16%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; P(p-CH3OC6H4)3; In toluene; at 130℃; for 15h;Inert atmosphere;	General procedure: [RhCl(cod)]2 (12 mg, 0.025 mmol), P(4-MeOC6H4)3 (53 mg, 0.15 mmol), B2(nep)2 (113 mg, 0.50mmol), 1a (110 mg, 0.50 mmol) and toluene (0.50 mL) were added to a 10 mL two-necked flask under a stream of nitrogen. The mixture was stirred at 130 C for 3 h, and then cooled to room temperature. Additional [RhCl(cod)]2 (12 mg, 0.025 mmol), P(4-MeOC6H4)3 (53 mg, 0.15 mmol)and B2(nep)2 (113 mg, 0.50 mmol) were added under a stream of nitrogen, and the mixture was heated at 130 C for 12 h. The mixture was cooled to room temperature and passed through NH silica to remove remaining 1a and phosphine ligand (eluent: hexane/EtOAc = 1/0 to 50/1, then EtOAc/MeOH = 10/1). The obtained crude product was further purified by flash column chromatography over SiO2 (eluent: hexane/EtOAc = 20/1 to 10/1) to give 5,5-dimethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborinane (2) [CAS: 22871-77-8] as a white solid (90mg, 75%).

Reference： [1]Chemistry Letters,2015,vol. 44,p. 366 - 368

40
[ 61912-15-0 ]
[ 501374-30-7 ]
[ 460743-71-9 ]

Yield	Reaction Conditions	Operation in experiment
17%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,3-bis(adamantan-2-yl)imidazolin-2-yliden chloride; sodium ethanolate; In toluene; at 130℃; for 20h;Sealed tube; Inert atmosphere;	General procedure: [RhCl(cod)]2 (7.4 mg, 0.015 mmol), I(2-Ad)·HCl (22 mg, 0.060 mmol), NaOEt (41 mg,0.60 mmol) and toluene (0.40 mL) were added to a 10 mL sample vial with a Teflonsealed screwcap in a glovebox filled with nitrogen, and the resulting mixture was stirredfor 10 min. Naphthalen-2-yl diisopropylcarbamate (10, 81 mg, 0.30 mmol),5,5-dimethyl-2-(p-tolyl)-1,3,2-dioxaborinane (4b, 92 mg, 0.45 mmol) and toluene (0.60mL) were then added to the vial, and the resulting mixture was sealed in the vessel andheated at 130 C for 20 h on an aluminum block. The mixture was then cooled to roomtemperature and purified directly by flash column chromatography over silica gel(eluent: hexane/EtOAc = 10:1) to give 2-(p-tolyl)naphthalene (38, 64 mg, 98%) as awhite solid.

Reference： [1]Tetrahedron,2015,vol. 71,p. 4484 - 4489

41
[ 92197-18-7 ]
[ 501374-30-7 ]
N,N-bis(propan-2-yl)-4-(trifluoromethyl)aniline [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 11048 - 11051

42
[ 402-44-8 ]
[ 201733-56-4 ]
[ 501374-30-7 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 12470 - 12473

43
N,N-dimethyl-2-methoxy-1-naphthamide [ No CAS ]
[ 501374-30-7 ]
[ 1415045-98-5 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4674 - 4677

44
[ 404574-87-4 ]
[ 501374-30-7 ]
[ 1415045-86-1 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4674 - 4677

45
[ 870-50-8 ]
[ 501374-30-7 ]
di-tert-butyl 1-(4-(trifluoromethyl)phenyl)hydrazine-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With water; copper diacetate; lithium tert-butoxide; In 1,2-dimethoxyethane; at 20℃;Inert atmosphere;	General procedure: To a 10-mL, two-necked flask (flask A) were added Cu(OAc)2 (4.5 mg, 0.025 mmol) and LiOt-Bu (60.0 mg, 0.75 mmol), and the atmosphere inside the flask was replaced with N2 by flushing (3 ×). To the flask, DME (0.5 mL) and H2O (4.5 μL, 0.025 mmol) were added and the mixture was stirred for over 15 min. To another 10-mL two-necked flask (flask B), arylboronic ester 1 (0.25 mmol) and di-tert-butyl azodicarboxylate (2, 115.1 mg, 0.5 mmol) were added, and after flushing the atmosphere in the flask with N2 (3 ×), DME (0.5 mL) was added. The solution in flask B was added to flask A via syringe within 1 min. Flask B was rinsed with DME (0.2 mL) and the solution was added to the flask A. After stirring for 13.5-16 h at r.t., the reaction was diluted with EtOAc (4 mL) and H2O (2-3 mL) and quenched with 1 M citric acid to neutralize the system. The organic layer was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel) to provide the hydrazine. Di-tert-butyl 1-[4-(Trifluoromethyl)phenyl]hydrazine-1,2-dicarboxylate (3e) [5,14]. White solid; yield: 57.1 mg (61%); Rf = 0.34 (hexane-EtOAc, 5:1). 1H NMR (400 MHz, CDCl3): δ = 1.52 (s, 18 H), [6.66, 6.84 (br s, 1 H)], 7.56 (m, 4 H). 13C NMR (100 MHz, CDCl3): δ = 28.2, 28.3, 82.2, 83.3, 122.4, 124.2 (q, J = 1079.3 Hz), 125.7, 126.9 (q, J = 129.6 Hz), 145.2, 153.1, 155.4.

Reference： [1]Synthesis,2015,vol. 47,p. 3746 - 3750

46
[ 402-43-7 ]
[ 1195-66-0 ]
[ 501374-30-7 ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 7009 - 7012

47
2-{4-(trifluoromethyl)phenoxy}pyridine [ No CAS ]
[ 201733-56-4 ]
[ 501374-30-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 2417 - 2421

48
tert-butyl methyl(4-(trifluoromethyl)benzoyl)carbamate [ No CAS ]
[ 201733-56-4 ]
[ 501374-30-7 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 8718 - 8722
Angew. Chem.,2016,vol. 128,p. 8860 - 8864,5

49
[ 42101-92-8 ]
[ 501374-30-7 ]
2-(4-(trifluoromethyl)benzyl)naphthalene [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 5572 - 5575

50
(S)-2-(naphthalen-2-yl)butan-2-yl acetate [ No CAS ]
[ 501374-30-7 ]
(R)-2-(2-(4-(trifluoromethyl)phenyl)butan-2-yl)naphthalene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12057 - 12060

51
[ 106376-16-3 ]
[ 201733-56-4 ]
[ 501374-30-7 ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 6692 - 6698

52
[ 110-87-2 ]
[ 501374-30-7 ]
[ 824431-48-3 ]

Yield	Reaction Conditions	Operation in experiment
24%	With bis(1,5-cyclooctadiene)nickel(0); 1,3-(dicyclohexyl)imidazol-2-ylidene hydrochloride; sodium t-butanolate; In toluene; at 140℃; for 12h;Sealed tube; Glovebox; Inert atmosphere;	General procedure: Ni(cod)2 (13.8 mg, 0.05 mmol, 10 mol%), ICy·HCl (26.8 mg, 0.10 mmol, 20mol%), NaOtBu (9.6mg, 0.10 mmol), and toluene (0.5 mL) were added to a 10 mL-sample vial with a Teflon-sealedscrewcap in a glove box filled with N2. The resulting mixture was stirred at room temperature for 5min. 3,4-Dihydro-2H-pyran (1, 42.1 mg, 0.50 mmol), 2a (122 mg, 0.60 mmol) and toluene (1.0 mL)were added to the vial and the cap was closed. The mixture was stirred at 140 C for 12 h. Afterbeing cooled to room temperature, the crude mixture was filtered through a pad of silica gel. Thefiltrate was concentrated in vacuo to give a residue, which was purified by column chromatographyover silica gel (eluent: hexane/EtOAc =9/1) to give 5-(4-methylphenyl)-4-penten-1-ol as a whitesolid (68 mg, 74% yield).

Reference： [1]Chemistry Letters,2016,vol. 45,p. 1277 - 1279

53
[ 2040-04-2 ]
[ 501374-30-7 ]
1-(3-methoxy-4′-[trifluoromethyl][1,1′-biphenyl]-2-yl)ethan-1-one [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 794 - 797

54
[ 447-60-9 ]
[ 501374-30-7 ]
2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6503 - 6510

55
[ 447-60-9 ]
[ 501374-30-7 ]
2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]benzonitrile [ No CAS ]
4,6-bis(3-methylphenyl)-2-(trifluoromethyl)benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6503 - 6510

56
[ 109-09-1 ]
[ 501374-30-7 ]
[ 203065-88-7 ]

Reference： [1]Organometallics,2017,vol. 36,p. 4363 - 4366

57
[ 623-00-7 ]
[ 501374-30-7 ]
[ 140483-60-9 ]

Reference： [1]Organometallics,2017,vol. 36,p. 4363 - 4366

58
[ 5145-65-3 ]
[ 501374-30-7 ]
[ 728-86-9 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 12584 - 12587

59
[ 42523-15-9 ]
[ 501374-30-7 ]
1-(4-(trifluoromethyl)phenyl)-9H-fluoren-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); at 150℃; for 4h;Microwave irradiation; Inert atmosphere;	General procedure: A dried Biotage microwave vial equipped with a magnetic stirring bar and anitrogen inlet was sequentially charged with fluorenone (1) (0.5 mmol), boronic ester (6) (0.5 - 1mmol), pinacolone (0.5 mL) and RuH2(CO)(PPh3)3 (10 mol%). The reaction mixture was heatedunder MW irradiation at 150 C for 2.5 - 8 h. The reaction mixture was extracted with EtOAc (15mL), washed with brine, subjected to filtration, dried (Na2SO4) and concentrated under reducedpressure. Purification using flash column chromatography on silica gel (eluting with 1:9hexanes/ethyl acetate) afforded product (2).

Reference： [1]Synlett,2017,vol. 28,p. 2587 - 2593

60
[ 898766-24-0 ]
[ 501374-30-7 ]
3,5-dimethyl-2-{4-(trifluoromethyl)phenyl}pivalophenone [ No CAS ]

Reference： [1]Organometallics,2017,vol. 36,p. 159 - 164

61
[ 184090-09-3 ]
[ 501374-30-7 ]
C₂₄H₂₁F₃O₅ [ No CAS ]

Reference： [1]Organometallics,2017,vol. 36,p. 159 - 164

62
[ 13621-25-5 ]
[ 501374-30-7 ]
C₁₉H₁₇F₃O [ No CAS ]

Reference： [1]Organometallics,2017,vol. 36,p. 159 - 164

63
[ 113845-69-5 ]
[ 201733-56-4 ]
[ 501374-30-7 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1995 - 1998

64
C₁₃H₂₀O₂ [ No CAS ]
[ 501374-30-7 ]
(2S,6S,E)-1-methoxy-5-methyl-7-(4-(trifluoromethyl)phenyl)undeca-3,5,6-trien-2-ol [ No CAS ]
(2R,6S,E)-1-methoxy-5-methyl-7-(4-(trifluoromethyl)phenyl)undeca-3,5,6-trien-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-ethyl-N,N-diisopropylamine; bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; water; at 25℃; for 12h;Inert atmosphere; Schlenk technique;	General procedure: A palladium complex, ligand, and the dry THF (half of the volume necessary for the reaction) were added successively into a Schlenk apparatus that is attached to an Ar line and stirred 15 minat 25 C. Then, the dry THF (remaining half volume) solution of organoboron, enyne oxirane (1), and degassed water were added successively. The mixture was stirred magnetically in a preheated water or an oil bath. When the reaction was complete, as judged by TLC analysis, the solvent was evaporated under reduced atmosphere and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate), affording the product 3 as colourless oil unless otherwise mentioned. In the case of optimization studies, the reaction mixture was filtered through a short silica gel column, washed with Et2O, dried with MgSO4 and evaporated under reduced atmosphere. The residue was analysed by 1H NMR using p-anisaldehyde as the internal standard. Aldehyde and methoxy hydrogen signals were used in the quantitative analyses.

Reference： [1]Tetrahedron,2018,vol. 74,p. 3652 - 3662

65
[ 5765-65-1 ]
[ 65051-83-4 ]
[ 501374-30-7 ]
4-((1S*,2R*,3S*)-2-methyl-2-phenyl-3-(4-(trifluoromethyl)phenyl)cyclopropyl)morpholine [ No CAS ]
4-(2-methyl-2-phenyl-3-(4-(trifluoromethyl)phenyl)cyclopropyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Add tetrahydrofuran as a solvent (2 ml) in a 25 ml reaction tube.Adding cuprous chloride (0.010 mmol) in turn,Dppbz L1 (5.4 mg, 0.06 mmol),Stir at room temperature for 2 min;Add m-CPBA (2 mg, 0.01 mmol),Sodium tert-butoxide (28.8 mg, 0.3 mmol) was stirred for 2 min;Then the substrate molar mass of 1.2 times the amount of 4-trifluoromethylphenylboronic acid neopentyl glycol ester (62 mg, 0.24 mmol), stirred for about 2 min;3-methyl-3-phenylcyclopropene (0.2 mmol) was added,The reaction system of benzoyloxymorpholine (50 mg, 0.24 mmol) was stirred at room temperature.TLC point plate monitoring, after the reaction is complete,Separated and purified by column chromatography,Obtaining an oily liquid which was subjected to 1H NMR (as shown in Figure 3),13C NMR (as shown in Figure 4),The structure was determined to be Equation 2, the weighing weight was 56 mg, the calculated yield was 78%, and dr=92:8;

Reference： [1]Patent: CN108530389,2018,A .Location in patent: Paragraph 0057; 0058; 0059
[2]Organic Letters,2019,vol. 21,p. 5432 - 5437

66
[ 591-50-4 ]
N-(2,4-dimethoxybenzyl)but-3-enamide [ No CAS ]
[ 501374-30-7 ]
N-(2,4-dimethoxybenzyl)-4-phenyl-3-(4-(trifluoromethyl)phenyl)butanamide [ No CAS ]