[ CAS No. 66107-29-7 ] {[proInfo.proName]}

Name: 66107-29-7|4-Methoxyphenyl trifluoromethanesulfonate|97%
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SKU: A235732
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3d Animation Molecule Structure of 66107-29-7

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Quality Control of [ 66107-29-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 66107-29-7 ]

SDS Specification

Alternatived Products of [ 66107-29-7 ]

Product Details of [ 66107-29-7 ]

CAS No. :	66107-29-7	MDL No. :	MFCD00209596
Formula :	C₈H₇F₃O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XSTNIRWDULKNJE-UHFFFAOYSA-N
M.W :	256.20	Pubchem ID :	579337
Synonyms :

Calculated chemistry of [ 66107-29-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	4
Num. H-bond acceptors :	7.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.58
TPSA :	60.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	2.64
Log Po/w (WLOGP) :	4.27
Log Po/w (MLOGP) :	1.67
Log Po/w (SILICOS-IT) :	1.33
Consensus Log Po/w :	2.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.11
Solubility :	0.201 mg/ml ; 0.000785 mol/l
Class :	Soluble
Log S (Ali) :	-3.57
Solubility :	0.0687 mg/ml ; 0.000268 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.08
Solubility :	0.213 mg/ml ; 0.00083 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.44

Safety of [ 66107-29-7 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501	UN#:	3082
Hazard Statements:	H302-H318	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 66107-29-7 ]

* 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.

Upstream synthesis route of [ 66107-29-7 ]
Downstream synthetic route of [ 66107-29-7 ]

[ 66107-29-7 ] Synthesis Path-Upstream 1~1

1
[ 66107-29-7 ]
[ 1445308-48-4 ]
[ 18229-94-2 ]
[ 52244-70-9 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14793 - 14797[2] Angew. Chem., 2016, vol. 128, # 47, p. 15013 - 15017,5

[ 66107-29-7 ] Synthesis Path-Downstream 1~108

1
[ 598-32-3 ]
[ 66107-29-7 ]
[ 104-20-1 ]
[ 141172-02-3 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

2
[ 111-34-2 ]
[ 66107-29-7 ]
[ 100-06-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 3654 - 3655
[2]Journal of Organic Chemistry,1993,vol. 58,p. 7421 - 7426

3
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 934-56-5 ]
[ 611-94-9 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

4
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 66680-87-3 ]
[ 22966-19-4 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

5
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 82994-41-0 ]
[ 56139-60-7 ]
[ 112533-12-7 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

6
[ 66107-29-7 ]
[ 151-50-8 ]
[ 874-90-8 ]

Reference： [1]Chemistry Letters,1989,p. 1957 - 1958
[2]Journal of the Chemical Society. Perkin transactions I,1989,p. 1365 - 1366
[3]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 1118 - 1121
[4]Chemical Communications,2006,p. 3001 - 3003

7
[ 66107-29-7 ]
pyridine-3-boronic acid 1,3-propanediol cyclic ester [ No CAS ]
[ 5958-02-1 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2201 - 2208

8
[ 358-23-6 ]
[ 150-76-5 ]
[ 66107-29-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridine; at 0 - 20℃;	Trifluoromethanesulfonic anhydride (6.74 mL, 41.1 mmol) was added to a solution of 4-methoxyphenol (5 g, 40.3 μmol) in pyridine (40 mL) at 0C, and then the mixture was stirred at room temperature overnight. After adding AcOEt and brine, organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude product was purified by flash column chromatography on silica gel (Toluene/AcOEt =30/1) to give compound 16 as a colorless liquid (10.0 g, 97% yield). 1H NMR (CDCl3, 400 MHz) : δ7.34-7.16 (m, 2H, Ph), 7.04-6.95 (m, 2H, Ph), 3.91 (s, 3H, Me) ; 13C NMR (CDCl3, 100 MHz) : δ159.0, 143.0, 122.3, 120.3, 117.2, 115.0, 55.7.
94%	With pyridine; In dichloromethane; at 0℃; for 2h;Inert atmosphere;	General procedure: Prepared following an adaptation of the published procedure.7 To a cooled (0 C), stirred solution of the phenol (10 mmol) and pyridine (20 mmol) in CH2Cl2 (50 mL) under Ar or N2 was added via syringe trifluoromethanesulfonic anhydride (13 mmol). After stirring for 1-3 h, the reaction mixture was treated with aq satd NH4Cl. The CH2Cl2 phase was separated and washed sequentially with aqueous copper sulfate (2x) and H2O and dried (MgSO4). Filtration, concentration of the filtrate in vacuo and purification afforded the product.
91%	With pyridine; In dichloromethane; at 0 - 20℃;	Dissolve p-methoxyphenol (124mg, 1mmol) and pyridine (159mg, 2mmol) in dichloromethane (5mL), cool to 0, add trifluoromethanesulfonic anhydride (564mg, 2mmol) dropwise, warm to room temperature and react overnight After the reaction is completed, add 30mL ice water, extract with dichloromethane (20mL×3), wash with ice 2% dilute hydrochloric acid and saturated brine successively, dry with anhydrous sodium sulfate, and concentrate to obtain the crude product. Column chromatography (petroleum ether/acetic acid Ethyl ester=20:1) to obtain 4-methoxyphenyl trifluoromethanesulfonate with a yield of 91%.

91%	With pyridine; In dichloromethane; at 0 - 20℃;	Step S1: Dissolve p-methoxyphenol (124mg, 1mmol) and pyridine (159mg, 2mmol) in dichloromethane (5mL), cool to 0, add trifluoromethanesulfonic anhydride (564mg, 2mmol) dropwise, warm to room temperature and react overnight After the reaction is completed, add 30mL ice water, extract with dichloromethane (20mL×3), wash with ice 2% dilute hydrochloric acid and saturated brine successively, dry with anhydrous sodium sulfate, and concentrate to obtain the crude product. Column chromatography (petroleum ether/acetic acid Ethyl ester=20:1) to obtain 4-methoxyphenyl trifluoromethanesulfonate with a yield of 91%.
65%	With pyridine; In dichloromethane; at 20℃;Inert atmosphere; Cooling with ice;	General procedure: To a flame-dried 25 mL round-bottom flask fitted with a rubber septum and equipped with a magnetic stir bar was added phenol (1.0 equiv). The contents were evacuated and backfilled three times with nitrogen. Anhydrous DCM (0.7 M) and distilled pyridine (4.2 equiv) were added via syringe and the stirred solution was cooled in an ice bath for 10 min. Triflic anhydride (1.4 equiv) was added dropwise over 5 min. The reaction was slowly warmed to room temperature. After 10-14 h, the reaction was diluted with Et2O (30 mL) and quenched with 1 M aqueous HCl (30 mL). The organic layer was extracted. The organic layer washed with water (2 x 25mL), then brine (25 mL), dried over MgSO4, filtered, and concentrated via rotary evaporation. The aryl triflate was purified by flash chromatography (gradient 2-20% EtOAc/hexanes over 45 column volumes.
	With pyridine; In dichloromethane; at 0 - 25℃; for 12h;Inert atmosphere;	General procedure: After phenols and pyridine were dissolved in dry DCM, triflic anhydridewas added slowly by syringe over 5 min at 0 C. Then the reaction mixture was allowed to bewarmed up to 25 C and further stirred at 25 C for 12 h. After the reaction mixture was quenche dwith water, the aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over Na2SO4 and then filtrated. The products were purified by regular flash chromatography (petroleumether/EtOAc mixtures) [10].
	With pyridine; In dichloromethane; at 0 - 25℃; for 12h;Inert atmosphere;	General procedure: Under N2 atmosphere, phenols and pyridine were dissolved in dry CH2Cl2, then, triflic anhydride was added slowly by syringe over 5 min at 0C. Then the reaction mixture was allowed to be warmed up to 25C and further stirred at 25C for 12 h. After the reaction mixture was quenched with water, the aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over Na2SO4 and then filtrated. The products were purified by regular flash chromatography (petroleum ether/EtOAc mixtures).1

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 472 - 480
[2]Chemical Communications,2018,vol. 54,p. 4398 - 4401
[3]Tetrahedron,1989,vol. 45,p. 6679 - 6682
[4]Angewandte Chemie - International Edition,2012,vol. 51,p. 4577 - 4580
[5]Tetrahedron Letters,2017,vol. 58,p. 3019 - 3023
[6]European Journal of Organic Chemistry,2021,vol. 2021,p. 309 - 313
[7]Journal of Organic Chemistry,2004,vol. 69,p. 1137 - 1143
[8]Journal of the American Chemical Society,2008,vol. 130,p. 15248 - 15249
[9]Chemistry - A European Journal,2009,vol. 15,p. 9336 - 9349
[10]Synthesis,2018,vol. 50,p. 4413 - 4428
[11]Journal of the American Chemical Society,1987,vol. 109,p. 5478
[12]Angewandte Chemie - International Edition,2017,vol. 56,p. 15693 - 15697
    Angew. Chem.,2017,vol. 129,p. 15899 - 15903,5
[13]Chemical Communications,2013,vol. 49,p. 9425 - 9427
[14]Patent: CN113527121,2021,A .Location in patent: Paragraph 0037-0038; 0046
[15]Patent: CN113527121,2021,A .Location in patent: Paragraph 0037-0038; 0046
[16]Angewandte Chemie - International Edition,2012,vol. 51,p. 5915 - 5919
[17]Chemistry - A European Journal,2013,vol. 19,p. 3504 - 3511
[18]Journal of Organic Chemistry,2020,vol. 85,p. 7097 - 7111
[19]Tetrahedron,2003,vol. 59,p. 10295 - 10305
[20]Journal of the American Chemical Society,2019,vol. 141,p. 12481 - 12486
[21]Organometallics,2014,vol. 33,p. 6171 - 6178
[22]Journal of Organic Chemistry,2018,vol. 83,p. 11178 - 11190
[23]Journal of the American Chemical Society,2012,vol. 134,p. 169 - 172
[24]Organometallics,2021,vol. 40,p. 2246 - 2252
[25]Tetrahedron,2018,vol. 74,p. 3314 - 3317
[26]Journal of Organic Chemistry,1983,vol. 48,p. 2887 - 2891
[27]Journal of the Chemical Society. Chemical communications,1987,p. 904 - 905
[28]Journal of Organic Chemistry,1997,vol. 62,p. 261 - 274
[29]Synthesis,2005,p. 547 - 550
[30]Organic Letters,2002,vol. 4,p. 4717 - 4718
[31]Synlett,2007,p. 2537 - 2540
[32]Chemistry - A European Journal,2007,vol. 13,p. 5937 - 5943
[33]Organic and Biomolecular Chemistry,2008,vol. 6,p. 169 - 174
[34]Tetrahedron,2009,vol. 65,p. 1951 - 1956
[35]Angewandte Chemie - International Edition,2011,vol. 50,p. 5943 - 5946
[36]Journal of Organic Chemistry,2012,vol. 77,p. 10468 - 10472
[37]Chemistry - A European Journal,2013,vol. 19,p. 6014 - 6020
[38]Journal of Organometallic Chemistry,2016,vol. 820,p. 120 - 124
[39]Angewandte Chemie - International Edition,2017,vol. 56,p. 15441 - 15445
    Angew. Chem.,2017,vol. 129,p. 15643 - 15647,5
[40]Angewandte Chemie - International Edition,2018,vol. 57,p. 13598 - 13602
    Angew. Chem.,2018,vol. 130,p. 13786 - 13790,5
[41]Journal of the American Chemical Society,2019,vol. 141,p. 6755 - 6764
[42]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5916 - 5919
[43]Organic Letters,2019,vol. 21,p. 5912 - 5916
[44]Journal of the American Chemical Society,2001,vol. 123,p. 8864 - 8865
[45]Journal of the American Chemical Society,2019,vol. 141,p. 11414 - 11419
[46]Tetrahedron Letters,2020,vol. 61
[47]Organometallics,2020,vol. 39,p. 2189 - 2196
[48]Journal of Organic Chemistry,2021,vol. 86,p. 466 - 474

9
[ 66107-29-7 ]
[ 292638-85-8 ]
[ 3901-07-3 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

10
[ 66107-29-7 ]
[ 98-80-6 ]
[ 613-37-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium fluoride; di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); In toluene; at 80℃; for 1.5h;Product distribution / selectivity;	Under a nitrogen atmosphere, 4-trifluoromethane-sulfonyloxyanisole (0.49g, 1.9mmol), phenylboronic acid (0.29g, 2.4mmol), potassium fluoride (0.24g, 4.2mmol), (ϖ-allyl)palladium chloride (3.6mg, 0.01mmol), 2,2-diphenyl-1-(di-tert-butylphosphino)-1-methylcyclopropane (14.0mg, 0.04mmol) obtained in Example 4 and toluene (4ml) were placed in a reaction flask and stirred for 1.5 hours at 80C. The reaction mixture was cooled, washed with water, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under reduced pressure, and the concentrate was purified by column chromatography to give the title compound (0.34g, 96%) as white crystal. 1H-NMR(CDCl3) δ 3.85 (s, 3H), 6.93-7.04 (m, 2H), 7.23-7.69 (m, 7H).

Reference： [1]Synlett,2007,p. 3206 - 3208
[2]Patent: WO2004/72088,2004,A2 .Location in patent: Page/Page column 49
[3]Organic Letters,2016,vol. 18,p. 3186 - 3189
[4]Journal of Organic Chemistry,2006,vol. 71,p. 685 - 692
[5]Chemistry - A European Journal,2007,vol. 13,p. 5937 - 5943
[6]Tetrahedron,1989,vol. 45,p. 6679 - 6682
[7]Organometallics,2017,vol. 36,p. 1822 - 1827

11
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 123-11-5 ]

Reference： [1]Synlett,2007,p. 2537 - 2540
[2]Synthesis,1996,p. 470 - 472

12
[ 66107-29-7 ]
[ 62-53-3 ]
[ 1208-86-2 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 1268 - 1273
[2]Journal of Organic Chemistry,2009,vol. 74,p. 4720 - 4726
[3]Journal of Medicinal Chemistry,2010,vol. 53,p. 5054 - 5058

13
[ 66107-29-7 ]
[ 73183-34-3 ]
[ 171364-79-7 ]

Reference： [1]Synthesis,2022,vol. 54,p. 1339 - 1346
[2]Tetrahedron,2001,vol. 57,p. 9813 - 9816
[3]Journal of the American Chemical Society,2017,vol. 139,p. 8621 - 8627
[4]Tetrahedron Letters,1997,vol. 38,p. 3447 - 3450
[5]ChemCatChem,2016,vol. 8,p. 2317 - 2320

14
[ 110-91-8 ]
[ 66107-29-7 ]
[ 27347-14-4 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 1479 - 1482
[2]Journal of Organic Chemistry,2004,vol. 69,p. 3173 - 3180
[3]Journal of Organic Chemistry,2000,vol. 65,p. 1158 - 1174
[4]Tetrahedron Letters,1997,vol. 38,p. 6363 - 6366

15
[ 66107-29-7 ]
[ 100-61-8 ]
[ 55251-46-2 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 6363 - 6366
[2]Journal of Organic Chemistry,2004,vol. 69,p. 3173 - 3180
[3]Organic Syntheses,2002,vol. 78,p. 23 - 23

16
[ 66107-29-7 ]
[ 78-94-4 ]
[ 3815-30-3 ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 4055 - 4058

17
[ 66107-29-7 ]
(E)-2-(tri-n-butylstannyl)-2-buten-1-ol [ No CAS ]
[ 129887-49-6 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 7600 - 7605

18
[ 66107-29-7 ]
[ 106-49-0 ]
[ 39253-43-5 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 1158 - 1174

19
[ 66107-29-7 ]
[ 100-01-6 ]
[ 730-11-0 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 1158 - 1174

20
[ 66107-29-7 ]
[ 115378-31-9 ]
[ 240420-43-3 ]

Reference： [1]Organic Letters,2000,vol. 2,p. 1089 - 1091
[2]Tetrahedron Letters,1999,vol. 40,p. 5263 - 5266

21
[ 66107-29-7 ]
trans-2-n-butylcyclopropylboronic acid [ No CAS ]
1-((1S,2S)-2-Butyl-cyclopropyl)-4-methoxy-benzene [ No CAS ]

Reference： [1]Synthesis,2000,p. 1095 - 1100

22
[ 37595-74-7 ]
[ 150-76-5 ]
[ 66107-29-7 ]

Reference： [1]Chemical Science,2022,vol. 13,p. 2270 - 2279
[2]Organic letters,2000,vol. 2,p. 477 - 480
[3]Organic Letters,2002,vol. 4,p. 1231 - 1233

23
[ 150-76-5 ]
(CF₃SO₂)2NC₆H₄-O-(PEG-3400)-OC₆H₄N(SO₂CF₃)2 [ No CAS ]
[ 66107-29-7 ]

Reference： [1]Organic letters,2000,vol. 2,p. 477 - 480

24
[ 66107-29-7 ]
[ 16419-60-6 ]
[ 92495-54-0 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 4020 - 4028

25
[ 34420-17-2 ]
[ 66107-29-7 ]
[ 14310-21-5 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 1465 - 1470

26
3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester [ No CAS ]
[ 66107-29-7 ]
3-(4-methoxyphenyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 555 - 560

27
[ 66107-29-7 ]
[ 13922-41-3 ]
[ 27331-33-5 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 4101 - 4111

28
[ 776-76-1 ]
[ 66107-29-7 ]
[ 14311-79-6 ]

Reference： [1]Synthesis,2006,p. 1771 - 1774

29
[ 66107-29-7 ]
[ 100-39-0 ]
[ 834-14-0 ]

Reference： [1]Organic Letters,1999,vol. 1,p. 1323 - 1326

30
[ 66107-29-7 ]
[ 5123-13-7 ]
[ 613-37-6 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 10596 - 10602

31
[ 66107-29-7 ]
[ 55-21-0 ]
[ 7472-54-0 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 13001 - 13007

32
[ 273-53-0 ]
[ 66107-29-7 ]
[ 838-34-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 169 - 174
[2]Journal of the American Chemical Society,2012,vol. 134,p. 169 - 172

33
[ 66107-29-7 ]
[ 66680-87-3 ]
[ 22966-19-4 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

34
[ 66107-29-7 ]
[ 934-56-5 ]
[ 611-94-9 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

35
[ 97-94-9 ]
[ 66107-29-7 ]
[ 1515-95-3 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 3688 - 3692

36
potassium N-(trifluoroboratomethyl)benzamide [ No CAS ]
[ 66107-29-7 ]
[ 41882-10-4 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4876 - 4879

37
[ 66107-29-7 ]
[ 104-92-7 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4974 - 4976
[2]Journal of the American Chemical Society,2010,vol. 132,p. 14076 - 14078
[3]Journal of the American Chemical Society,2012,vol. 134,p. 14760 - 14763

38
[ 66107-29-7 ]
[ 5720-07-0 ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol %), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol %) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3×10 mL). The aqueous layer was then cooled to 0 C (ice bath) and acidified to pH ≤1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3×10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid.

Reference： [1]Tetrahedron,2011,vol. 67,p. 576 - 583
[2]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673
[3]Organic Letters,2012,vol. 14,p. 4814 - 4817,4

39
[ 66107-29-7 ]
[ 288-36-8 ]
[ 68535-51-3 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8944 - 8947

40
[ 66107-29-7 ]
[ 142-29-0 ]
(S)-3-(4-methoxyphenyl)cyclopentene [ No CAS ]
4-p-anisylcyclopentene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 70℃; for 21h;Inert atmosphere; Glovebox;	General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee.

Reference： [1]Chemical Communications,2013,vol. 49,p. 9425 - 9427
[2]Patent: WO2014/196930,2014,A1 .Location in patent: Page/Page column 29; 30

41
[ 66107-29-7 ]
[ 58101-60-3 ]
[ 1499187-59-5 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 11758 - 11760

42
[ 2446-83-5 ]
[ 66107-29-7 ]
diisopropyl 1-(4-methoxyphenyl)-hydrazine-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: To a stirred solution of DIAD (1.2 mmol) in DMF (2 mL) at 0 C,NaH (0.05 g, 1.2 mmol) was added in portions over 20 min.Then, the aryl O-triflate (1.0 mmol), LiI (134 mg, 1mmol), andCu2O (15 mg, 0.1 mmol) were added to the reaction mixture,which was stirred at 80 C for 8 h under N2. The reaction wascooled and quenched by adding CH2Cl2 (2 mL) and sat. aq NH4Cl(3 mL). The mixture was stirred for an additional 30 min, andtwo layers were separated. The aqueous layer was extractedwith CH2Cl2 (3 × 2 mL), the combined organic layers were driedover MgSO4, filtered, and concentrated in vacuo. The residuewas purified by chromatography (silica gel; hexane-EtOAc, 3:1)to give the product.

Reference： [1]Synlett,2015,vol. 26,p. 942 - 944

43
[ 66107-29-7 ]
[ 70-55-3 ]
[ 1150-26-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrabutylammonium acetate; palladium diacetate; at 35℃; for 4h;Green chemistry;	General procedure: A mixture of Pd(OAc)2 (5 mg, 0.02 mmol), aryl source (1 mmol), sulfonamide source (1.0 mmol), Cu(OAc)2 (9 mg, 0.05 mmol; in the presence of sulfonyl azides), and TBAA (2.0 mmol) in PEG-400 (3 g) was stirred for the appropriate time at 35-50C under air. The crude reaction mixture was diluted with EtOAc (5 mL) and a saturated NH4Cl solution (5 mL). The mixture was stirred for an additional 30 min and the layers were separated. The aqueous layer was extracted with EtOAc (6 mL × 3). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuo. The residue was purified by column chromatography (silica gel, hexane:EtOAc 1:3) to give the desired product. Spectral data for all compounds except 6c, 6f, and 6n have been reported in previous reports.[19,30,31]

Reference： [1]Journal of Sulfur Chemistry,2016,vol. 37,p. 211 - 221

44
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 98-80-6 ]
[ 611-94-9 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 86502 - 86509

45
[ 66107-29-7 ]
[ 4559-70-0 ]
[ 795-44-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0); sodium carbonate; In 1,4-dioxane; at 80℃; for 20h;Inert atmosphere;	General procedure: Under a N2 atmosphere, 0.2 mmol aryl triflate 1a, 0.2 mmol Ph2P(O)H 2a,10 mol% Ni(COD)2, 10 mol% dppf,1.0 equiv Na2CO3 and 2 mL dioxane were charged into a 10 mL schlenck tube. The mixturewas stirred at 80 C for 20 h. After removal of the volatile, the residues were passed through a short silica chromatography (particlesize 37-54 mm, petroleum ether/ethyl acetate as eluent) toafford analytically pure organophosphorus compounds 3. Purification by chromatography (petroleum ether/EtOAc = 1:2) afforded 3e (52.4 mg, 85%) as a white solid. Rf = 0.50 (EtOAc); 1H NMR (400 MHz CDCl3): δ 7.66 (dd, J = 8.0 Hz, J = 12.0 Hz, 4H), 7.61-7.52 (m, 4H), 7.47-7.44 (m, 4H), 6.97 (d, J = 7.6 Hz, 2H), 3.84 (s, 3H). 13C NMR (100 MHz CDCl3): δ 162.53 (d, JC-P = 2.7 Hz), 133.98 (d, JC-P = 11.2 Hz), 132.89 (d, JC-P = 104.0 Hz), 132.06 (d, JC-P = 9.8 Hz), 131.85 (d, JC-P = 2.7 Hz), 128.48 (d, JC-P = 12.0 Hz), 123.48 (d, JC-P = 109.9 Hz), 114.12 (d, JC-P = 13.1 Hz), 55.37. 31P NMR (162 MHz CDCl3): δ 29.28 ppm.

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 820,p. 120 - 124
[2]Cuihua Xuebao/Chinese Journal of Catalysis,2019,vol. 40,p. 1841 - 1846
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2021

46
[ 66107-29-7 ]
[ 100-58-3 ]
[ 613-37-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With C17H36ClN6NiP2(1+)*Cl(1-); In tetrahydrofuran; for 6h;Inert atmosphere;	General procedure: Substrate (0.1 mmol) and catalyst (2 mol%, 2 μmol) were mixed in 3 cm3 THF, organomagnesium reagent(1.3 mmol) was added at room temperature. After 6 h at 60 C, 1.5 cm3 NaCl solution (15%) was added carefully, the organic layer was dried over MgSO4, evaporated and purified via silica column chromatography.

Reference： [1]Monatshefte fur Chemie,2017,vol. 148,p. 105 - 109

47
[ 66107-29-7 ]
[ 38111-44-3 ]
[ 613-37-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With C17H36ClN6NiP2(1+)*Cl(1-); lithium chloride; In tetrahydrofuran; at 60℃; for 6h;Inert atmosphere;	General procedure: Substrate (0.1 mmol) and catalyst (2 mol%, 2 μmol) were mixed in 3 cm3 THF, organozinc reagent (1.3 mmol), and LiCl (1.3 mmol) were added at room temperature. After 6 h at 60 C, the solution was allowed to reach room temperature. NaCl solution (15%, 1 cm3) was added carefully, the organic layer was dried over MgSO4, evaporated and purified via silica column chromatography.

Reference： [1]Monatshefte fur Chemie,2017,vol. 148,p. 105 - 109

48
[ 66107-29-7 ]
[ 6638-79-5 ]
[ 13939-06-5 ]
[ 52898-49-4 ]

Reference： [1]Australian Journal of Chemistry,2017,vol. 70,p. 44 - 51

49
[ 66107-29-7 ]
[ 75-26-3 ]
[ 104-45-0 ]
[ 4132-48-3 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 14793 - 14797
Angew. Chem.,2016,vol. 128,p. 15013 - 15017,5

50
[ 66107-29-7 ]
[ 75-26-3 ]
[ 4132-48-3 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 14793 - 14797
Angew. Chem.,2016,vol. 128,p. 15013 - 15017,5

51
[ 75-29-6 ]
[ 66107-29-7 ]
[ 104-45-0 ]
[ 4132-48-3 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 14793 - 14797
Angew. Chem.,2016,vol. 128,p. 15013 - 15017,5

52
[ 66107-29-7 ]
[ 1068-55-9 ]
[ 104-45-0 ]
[ 4132-48-3 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 14793 - 14797
Angew. Chem.,2016,vol. 128,p. 15013 - 15017,5

53
[ 225931-80-6 ]
[ 1160861-53-9 ]
[ 66107-29-7 ]
C₃₉H₅₆F₃O₆PPdS [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 3177 - 3181
Angew. Chem.,2017,vol. 129,p. 3225 - 3229,5

54
[ 66107-29-7 ]
[ 102735-44-4 ]
benzyl 4,6-O-benzylidene-2-deoxy-2-(4-methoxyphenylamino)-α-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With tBuXPhos Pd G3; sodium t-butanolate; tert-butyl XPhos; In toluene; for 2h;Inert atmosphere; Reflux;	A mixture of glucosamine derivative 5 (500 mg, 1.20 mmol), triflate 16 (460.3 mg, 1.80 mmol), tBuXPhos Pd G3 (95.3 mg, 0.120 mmol), tBuXPhos (51.0 mg, 0.120 mmol), and tBuONa (462 mg, 4.80 mmol) was stirred in toluene (24 mL) under Ar and refluxed for 2 h. After diluting with AcOEt, the organic phase was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude product was purified by flash column chromatography on silica gel (Toluene/AcOEt = 10/1) to give compound 19 (401.6 mg, 73% yield) as a colorless oil. 1H NMR (CDCl3, 400 MHz) : δ7.53-7.51 (m, 2H, Ph), 7.37-7.30 (m, 8H, Ph), 6.77-6.74 (m, 2H, MeOPh), 6.69-6.65 (m, 2H, MeOPh), 5.60 (s, 1H, PhCH), 4.93 (d, J = 3.66 Hz, 1H, H-1), 4.73 (d, J = 11.9 Hz, 1H, PhCH2), 4.46 (d, J = 11.9 Hz, 1H, PhCH2), 4.26 (dd, J = 10.1, 4.58 Hz, 1H, H-6), 4.00 (t, J = 9.62 Hz, 1H, H-3), 3.96-3.91 (m, 1H, H-5), 3.78 (t, J = 10.1 Hz, 1H, H-6’), 3.69 (t, J = 9.62 Hz, 1H, H-4), 3.48 (dd, J = 9.62, 3.66 Hz, 1H, H-2), 2.83 (brs, 1H, OH) ; 13C NMR (CDCl3, 100 MHz) : δ147.4, 137.1, 136.9, 129.1, 128.4, 128.2, 127.9, 127.8, 126.3, 121.2, 118.1, 111.7, 109.9, 101.9, 97.1, 81.8, 70.6, 70.0, 69.0, 62.8, 59.0, 55.4 ; HRMS : C27H30NO6 [M+H]+ calcd : 464.2068, found : 464.2056.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3019 - 3023

55
[ 1295-35-8 ]
[ 66107-29-7 ]
[ 7550-35-8 ]
[ 2622-14-2 ]
trans-bromo(4-methoxyphenyl)bis(tricyclohexylphosphine)nickel(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In tetrahydrofuran; at 20℃; for 3h;Inert atmosphere;	To a solution of 2-naphthyl triflate (1a; 1.38 g, 5.00 mmol) and LiBr(478 mg, 5.50 mmol) in THF (20 mL) were added PCy3 (4.21 g, 15.0mmol) and Ni(cod)2 (1.38 g, 5.02 mmol) at r.t. After stirring for 2 h at this temperature, the solution was concentrated under reduced pressure. The residue was washed with n-hexane and MeOH to give 6 as ayellow solid; yield: 3.50 g (4.23 mmol, 85%); mp 122 C (dec.). IR (ZnSe): 731, 818, 849, 935, 1003, 1026, 1173, 1202, 1445, 1572,1748, 2845, 2924 cm-1. 1H NMR (C6D6, 400 MHz): δ = 0.85-1.30 (m, 18 H, Haliph), 1.47-1.57(m, 6 H, Haliph), 1.60-1.88 (m, 24 H, Haliph), 2.05-2.23 (m, 18 H, Haliph), 7.13-7.19 (m, 1 H, Harom), 7.29 (dd, J = 8.0, 8.0 Hz, 1 H, Harom), 7.40 (d, J = 8.0 Hz, 1 H, Harom), 7.59 (d, J = 8.0 Hz, 1 H, Harom), 7.65 (d, J = 8.0 Hz,1 H, Harom), 8.05 (s, 1 H, Harom), 8.15 (d, J = 8.0 Hz, 1 H, Harom). 13C{1H} NMR (C6D6, 100 MHz): δ = 27.5 (6 C, 6 CH2), 28.67 (6 C, 6 CH2), 28.71 (6 C, 6 CH2), 31.0 (6 C, 6 CH2), 31.1 (6 C, 6 CH2), 35.4 (t, 1JC-P = 8.7Hz, 6 C, 6 PCH), 123.9 (CH), 124.3 (CH), 126.1 (2 C, 2 CH), 131.3 (C), 133.6 (C), 138.2 (CH), 138.6 (CH), 150.1 (t, 2JC-P = 33.5 Hz, NiC). One signal for aromatic CH carbon overlapped with the solvent peak. 31P{1H} NMR (C6D6, 160 MHz): δ = 11.6 (s). HRMS (ESI+): m/z [M - Br]+ calcd for C46H73NiP2+: 745.4535; found: 745.4520.

Reference： [1]Synthesis,2017,vol. 49,p. 3590 - 3601

56
[ 421-83-0 ]
[ 150-76-5 ]
[ 66107-29-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 24h;	General procedure: A mixture of phenol (0.45 g, 5 mmol), trifluoromethanesulfonyl chloride (0.8 mL, 7.5 mmol) and Et3N (1.4 mL, 10 mmol) in THF (30 mL) was stirred at 0 C for 24 h. The solvent was evaporated and to the resulting residue were added H2O (20 mL) and EtOAc (20 mL). The organic phase was decanted and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (hexane/EtOAc, 4:1) gave the pure triflate in 85% yield (191 mg).

Reference： [1]Chemical Communications,2017,vol. 53,p. 11584 - 11587
[2]Synthesis,2017,vol. 49,p. 5025 - 5038

57
[ 120-72-9 ]
[ 66107-29-7 ]
[ 5782-23-0 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5388 - 5391
[2]Journal of Organic Chemistry,2020,vol. 85,p. 10902 - 10912

58
[ 327-54-8 ]
[ 66107-29-7 ]
[ 1206164-34-2 ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 7421 - 7430

59
[ 66107-29-7 ]
[ 3393-77-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; sulfur; sodium t-butanolate; In N,N-dimethyl-formamide; at 120℃; for 9h;Inert atmosphere;	General procedure: A one-necked flask was charged with CuI (10 mg, 0.05 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (16 mg, 0.5 mmol), phenolic ester (1 mmol), anhyd DMF (2 mL) under an inert atmosphere. The mixture was magnetically stirred and heated at 120 C for the appropriate reaction time (Table 6). After completion of the reaction, the mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (n-hexane/EtOAc) gave the desired symmetrical diaryl sulfides in 75-93% yields.

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038
[2]Applied Organometallic Chemistry,2019,vol. 33

60
[ 66107-29-7 ]
[ 98-80-6 ]
[ 5633-57-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; sulfur; sodium t-butanolate; at 60 - 80℃; for 16h;	General procedure: A one-necked flask was charged with CuI (30 mg, 0.15 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (47 mg, 1.5 mmol), phenolic ester (1 mmol), arylboronic acid (1.1 mmol), and PEG200 (2 mL). The mixture was magnetically stirred and heated at 60-80 C for the appropriate reaction time (Table 2). After completion of the reaction, the reaction mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silicagel (n-hexane/EtOAc) gave the desired unsymmetrical diaryl sulfides in 74-95% yields.

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038
[2]Applied Organometallic Chemistry,2019,vol. 33

61
[ 66107-29-7 ]
[ 5720-05-8 ]
[ 6013-47-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; sulfur; sodium t-butanolate; at 60 - 80℃; for 19h;	General procedure: A one-necked flask was charged with CuI (30 mg, 0.15 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (47 mg, 1.5 mmol), phenolic ester (1 mmol), arylboronic acid (1.1 mmol), and PEG200 (2 mL). The mixture was magnetically stirred and heated at 60-80 C for the appropriate reaction time (Table 2). After completion of the reaction, the reaction mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silicagel (n-hexane/EtOAc) gave the desired unsymmetrical diaryl sulfides in 74-95% yields.

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038
[2]Applied Organometallic Chemistry,2019,vol. 33

62
[ 66107-29-7 ]
[ 639-58-7 ]
[ 5633-57-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium fluoride; copper diacetate; potassium carbonate; sulfur; at 80℃; for 8h;	General procedure: A one-necked flask was charged with Cu(OAc)2 (30 mg, 0.15 mmol), K2CO3 (414 mg, 3.0 mmol), S8 (48 mg, 1.5 mmol), KF (180 mg, 3 mmol), phenolic ester (1 mmol), triphenyltin chloride (0.35 mmol), and PEG200 (1.5 mL). The mixture was magnetically stirred and heatedat 80 C for the appropriate reaction time (Table 4). After completion of the reaction, the reaction mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (n-hexane/EtOAc) gave the desired phenyl aryl sulfides in 79-94% yields.

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038
[2]Applied Organometallic Chemistry,2019,vol. 33

63
[ 5381-20-4 ]
[ 66107-29-7 ]
[ 39620-22-9 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15441 - 15445
Angew. Chem.,2017,vol. 129,p. 15643 - 15647,5

64
[ 66107-29-7 ]
[ 1205-17-0 ]
C₁₈H₁₈O₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15441 - 15445
Angew. Chem.,2017,vol. 129,p. 15643 - 15647,5

65
[ 66107-29-7 ]
[ 13149-00-3 ]
[ 6966-15-0 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1191 - 1194

66
[ 1191-99-7 ]
[ 66107-29-7 ]
[ 79623-15-7 ]

Yield	Reaction Conditions	Operation in experiment
< 10%	With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl-ammonium chloride; sodium formate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	General procedure: To a flame-dried 0.5-dram vial fitted with a rubber septum and equipped with a magnetic stir bar was added aryl triflate (1.0 equiv), Pd2dba3 (10 mol %), TBAC (1.5 equiv) and NaHCO2 (1.2 equiv). The contents were evacuated and backfilled three times with argon. 2,3-Dihydrofuran (DHF) (5.2 equiv) and DMF (0.7 M) was added via syringe and the reaction vial was sealed with a screw-top cap. The reaction mixture was stirred at room temperature for 14-16 hours. The reaction was diluted with Et2O (3 mL) and filtered through a 3 cm pad of silica, flushing with 35 mL of Et2O. The solution was concentrated via rotary evaporation. The reductive-Heck product was isolated by flash chromatography (gradient 2 to 20% EtOAc/hexanes). NOTE: The reaction is sensitive to water. Precaution to exclude moisture from hydroscopic reagents must be taken. DMF was degassed and dried over 3 Å molecular sieves and was stored under argon for up to one week. NaHCO2 was dried in a scintillation vial and lightly heated with a laboratory heat gun under vacuum. It was stored in a dry-box with Drierite (CaSO4) desiccant for up to 1 week. 2,3-Dihydrofuran was purified via short-path distillation under argon.

Reference： [1]Tetrahedron,2018,vol. 74,p. 3314 - 3317

67
[ 66107-29-7 ]
C₁₄H₂₁GeNO₃ [ No CAS ]
C₂₁H₂₇GeNO₄ [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 9287 - 9291

68
[ 66107-29-7 ]
[ 75-05-8 ]
[ 874-90-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With [2,2]bipyridinyl; bis(acetylacetonate)nickel(II); 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene; at 80℃; for 24h;Inert atmosphere;	2.6 mg (10 mmol) of nickel (II) acetylacetonate (manufactured by Sigma-Aldrich), 2,2'-bipyridine (manufactured by Tokyo Chemical Industry Co., Ltd.) 1 , 18.0 μL (100 mmol) of <strong>[66107-29-7]4-methoxyphenyl triflate</strong> (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and dissolved in 3.0 mL of acetonitrile (manufactured by Kanto Kagaku Co., Ltd.). 706 mg (250 mmol) of Me4BTDP was added, and the mixture was stirred under an Ar atmosphere at 80 C. for 24 hours. Thereafter, 3.7 mg (20 mmol) of ferrocene (manufactured by Tokyo Chemical Industry Co., Ltd.) was added as an internal standard, the reaction solution was concentrated and 1 H NMR (400 MHz, CDCl 3) measurement was carried out,The yield of 4-methoxybenzonitrile was 64%.

Reference： [1]Chemical Science,2019,vol. 10,p. 994 - 999
[2]Patent: JP2018/138534,2018,A .Location in patent: Paragraph 0034

69
[ 23210-22-2 ]
[ 66107-29-7 ]
3-(4-methoxyphenyl)-3-methyl-1-phenylindolin-2-one [ No CAS ]
3-(4-methoxyphenyl)-3-methyl-1-phenylindolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (S)-3-(tert-butyl)-4-(2,6-dimethoxy-3,5-dimethylphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole; caesium carbonate; bis(dibenzylideneacetone)-palladium(0); In toluene; at 60℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar, was charged under an N2 atmosphere with 3-methyl-N-phenylindolin-2-one (24) (100 mg, 0.45 mmol), the aryl triflate (1.1 equiv),Pd(dba)2 (25 mg, 0.045 mmol), Me2-BI-DIME (32) (18 mg, 0.053mmol), Cs2CO3 (291 mg, 0.894 mmol). Degassed (Ar sparged) toluene(1.0 mL) was charged to the vial which was then sealed with a crimpcap septum. The vial was heated at 60 C for 24 h. The reaction mixture was then cooled to room temperature and filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (5 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude product was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the desired product.

Reference： [1]Synthesis,2018,vol. 50,p. 4435 - 4443

70
[ 3017-70-7 ]
[ 66107-29-7 ]
6b,9a-dimethyl-8-((E)-styryl)-6b,9a-dihydroacenaphtho[1,2-d][1,3,2]dioxaborole [ No CAS ]
1-(4-methoxyphenyl)-3,4-dimethyl-1-phenylpent-3-en-2-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 15181 - 15185

71
[ 3017-70-7 ]
[ 66107-29-7 ]
6b,9a-dimethyl-8-((E)-styryl)-6b,9a-dihydroacenaphtho[1,2-d][1,3,2]dioxaborole [ No CAS ]
(1R,2R)-1-(4-methoxyphenyl)-3,4-dimethyl-1-phenylpent-3-en-2-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 15181 - 15185

72
[ 20157-44-2 ]
[ 66107-29-7 ]
[ 1027335-59-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5916 - 5919

73
[ 66107-29-7 ]
[ 102908-37-2 ]
[ 1078710-41-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5916 - 5919

74
[ 461-81-4 ]
[ 66107-29-7 ]
[ 777063-53-3 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 10978 - 10983

75
[ 66107-29-7 ]
[ 104-88-1 ]
[ 52988-34-8 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 10978 - 10983

76
[ 52605-96-6 ]
[ 66107-29-7 ]
3-methoxy-2-(4-methoxyphenyl)pyridine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 10978 - 10983

77
[ 920759-93-9 ]
[ 66107-29-7 ]
methyl 4'-methoxy-6-methyl-[1,1'-biphenyl]-2-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 10978 - 10983

78
[ 2555-28-4 ]
[ 66107-29-7 ]
7-methoxy-4-(4-methoxybenzyl)coumarin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With Xantphos Pd G3; lithium hexamethyldisilazane; In tetrahydrofuran; at 70℃; for 24h;	All reactions were prepared at the 1.0 mmol scale in a glovebox using an 8-mL screw cap vial with a Teflon-coated stir bar. The vial was charged with 4% Xantphos Pd G3 (0.038 g, 0.04 mmol), 7-methoxy-4-methylcoumarin (0.190g, 1mmol), and an aryl triflate (1.05 mmol). Next, 3 mL of a 1.0 M LiHMDS solution was added. Finally, 2 mL of THF was added to the reaction. The vial was capped, removed from the glovebox, and allowed to stir on an aluminum block preheated to 70 C for 24 hours. Upon completion, the reaction was allowed to cool. A standard workup was completed using about 2.5 mL of a 2.0 M HCl solution and dichloromethane to extract. Magnesium sulfate was utilized to dry the sample before gravity filtering and removing the solvent under reduced pressure. Completion was checked using TLC and GC-MS. The crude reaction mixture was loaded onto a silica gel column using a wet load technique. The yields reported are from one trial only. 7-Methoxy-4-(4-methoxybenzyl)-coumarin (2). Using the general procedure outlined above with 4-methoxyphenyl-trifluoromethanesulfonate (0.269 g, 195 μL), the crude reaction mixture was purified using column flash chromatography (silica gel, 60Å) with 60% petroleum ether / 30% DCM/ 10% ethyl acetate (Rf = 0.25) and 0.250 g (84%) of a yellow powder was isolated. The spectral data matched those for compound 2 reported for the aryl bromide reaction above.

Reference： [1]Tetrahedron Letters,2019,vol. 60

79
[ 66107-29-7 ]
[ 4559-70-0 ]
[ 34253-15-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium phosphate; In toluene; at 100℃; for 20h;Inert atmosphere; Sealed tube;	This embodiment provides a method for preparing 4-methoxyphenyl diphenylphosphinate, as follows: Under a nitrogen atmosphere, Add 0.30 mmol of diphenylphosphine oxide to the reactor, 0.20mmol <strong>[66107-29-7]4-methoxyphenyl trifluoromethanesulfonate</strong>, 0.50mmol potassium phosphate, 1.5mL toluene solvent, heated to 100 C after sealing the tube, and continued stirring for 20h, Stop the reaction, cool to room temperature, wash with water to remove excess alkali and generated salts, extract the aqueous phase with dichloromethane to obtain the organic phase, dry over anhydrous sodium sulfate, distill off the solvent under reduced pressure, and obtain the crude product by column chromatography The target product is isolated in 75% yield.
75%	With potassium phosphate; In toluene; at 100℃; for 20h;Inert atmosphere; Schlenk technique;	General procedure: Under N2 atmosphere, 0.2 mmol phenyl triflate 1a, 0.3 mmol Ph2P(O)H 2a, 2.5 equiv K3PO4 and 2 mL toluene were charged into a 10 mL schlenk tube. The mixture was stirred at 100C for 20 h. After removal of the volatile, the residues were passed through a short silica chromatography (particle size 37~54 mm, petroleum ether/ethyl acetate as eluent) to afford analytically pure organophosphorus compounds 3.

Reference： [1]Patent: CN110903316,2020,A .Location in patent: Paragraph 0065-0067
[2]Tetrahedron Letters,2020,vol. 61

80
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 135-19-3 ]
[ 444112-92-9 ]

Reference： [1]Journal of Catalysis,2020,vol. 389,p. 502 - 505

81
[ 90-15-3 ]
[ 201230-82-2 ]
[ 66107-29-7 ]
4-methoxyphenyl 1-naphthoate [ No CAS ]

Reference： [1]Journal of Catalysis,2020,vol. 389,p. 502 - 505

82
[ 24764-40-7 ]
[ 201230-82-2 ]
[ 66107-29-7 ]
(1-(tert-butyl)-1H-pyrrol-3-yl)(4-methoxyphenyl)methanone [ No CAS ]

Reference： [1]Chemical Science,2020,vol. 11,p. 8610 - 8616

83
[ 24764-40-7 ]
[ 201230-82-2 ]
[ 66107-29-7 ]
(1-(tert-butyl)-1H-pyrrol-3-yl)(4-methoxyphenyl)methanone [ No CAS ]
C₁₆H₁₉NO₂ [ No CAS ]

Reference： [1]Chemical Science,2020,vol. 11,p. 8610 - 8616

84
[ 83-24-9 ]
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 102237-68-3 ]

Reference： [1]Chemical Science,2020,vol. 11,p. 8610 - 8616

85
[ 603-76-9 ]
[ 201230-82-2 ]
[ 66107-29-7 ]
(4-methoxyphenyl)(1-methyl-1H-indol-3-yl)methanone [ No CAS ]

Reference： [1]Chemical Science,2020,vol. 11,p. 8610 - 8616

86
[ 875-79-6 ]
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 1352799-85-9 ]

Reference： [1]Chemical Science,2020,vol. 11,p. 8610 - 8616

87
[ 1632-83-3 ]
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 85510-69-6 ]

Reference： [1]Chemical Science,2020,vol. 11,p. 8610 - 8616

88
[ 100-42-5 ]
[ 201230-82-2 ]
[ 66107-29-7 ]
[ 73183-34-3 ]
(E)-2-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-en-1-yl 4-methoxybenzoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 17055 - 17061
Angew. Chem.,2020,vol. 132,p. 17203 - 17209,7

89
[ 50978-45-5 ]
[ 66107-29-7 ]
[ 123-11-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylsilane; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate; In acetonitrile; at 80℃; for 16h;Inert atmosphere; Sealed tube;	General procedure: CAUTION To avoid an unexpected leak of toxic CO and an increase in the internal pressure of the reaction vessel, all reactions should be conducted behind a blast shield in a well-ventilated fume hood. Pd(OAc)2 (2.2 mg, 10.0 mmol, 5.00 mol%), DPPF (8.3 mg, 15.0 mmol, 7.50 mol%), 2 (63.4 mg, 0.300 mmol, 1.50 equiv), and MeCN (1.00 mL) were added to an oven-dried, 10-mL test tube with a septum containing a magnetic stirring bar. The tube was evacuated and backfilled with Ar three times. Aryl triflate 1 (0.200 mmol), Et3SiH (47.8 mL, 0.300 mmol, 1.50 equiv), and Na2CO3 (31.8 mg, 0.300 mmol, 1.50 equiv) were added to the mixture under Ar flow. The tube was tightly screw-capped and heated to 80 C in an oil bath. The mixture was stirred for 16 h. After cooling to room temperature, the mixture was diluted with CH2Cl2 and H2O, extracted with CH2Cl2 from aqueous layer, washed with brine, dried over Na2SO4, filtered, and concentrated. After the 1H NMR analysis of the crude reaction mixture with a small amount of 1,2,4,5-tetramethylbenzene as an internal standard, the obtained residue was purified by preparative TLC (SiO2, developed with hexane/EtOAc mixture). The desired aldehyde was eluted just after finishing the development of the preparative TLC plate to prevent undesirable oxidation to carboxylic acid on SiO2. Further purification by recycling preparative HPLC afforded the analytically pure product. The 1-mmol scale experiment was conducted in a 26-mL test tube.

Reference： [1]Tetrahedron,2020,vol. 76

90
[ 1719-58-0 ]
[ 66107-29-7 ]
ethenyl-(4-methoxyphenyl)-dimethylsilane [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 23083 - 23088
Angew. Chem.,2020,vol. 132,p. 23283 - 23288,6

91
[ 7188-38-7 ]
[ 66107-29-7 ]
[ 19486-73-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 4,5-dimethyl-1,3-bis-(2,4,6-trimethylphenyl)-3H-imidazol-1-ium chloride; water; nickel dibromide; sodium t-butanolate; In toluene; at 150℃; for 20h;Schlenk technique; Inert atmosphere; Sealed tube;	General procedure: In a 25 ml flame-dried Schlenk tube, aryl/alkenyl (pseudo)halides (0.2 mmol), tert-butyl isocyanide (0.2 mmol), NiBr2 (10 mol%, 0.02 mmol), L1 (20 mol%, 0.04 mmol), tBuONa (2 equiv, 0.4 mmol), toluene (0.3 ml), H2O (0.1 ml) were added sequentially under nitrogen. The tube was sealed and stirred at 150 C for 20 h. After completion, the reaction mixture was filtered through a short pad of silica gel and washed with ethyl acetate (20 ml). The combined organic phase was concentrated and purified by silica gel column chromatography (Petroleum ether : Ethyl acetate = 30 : 1) to provide the product 3.

Reference： [1]Tetrahedron Letters,2020,vol. 61

92
[ 100-42-5 ]
[ 66107-29-7 ]
[ 14310-21-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With nickel(II) bromide trihydrate; rac-1,2-diphenylethylene-1,2-diamine; cesium fluoride; In tetrahydrofuran; at 25℃; for 12h;Sealed tube;	In a nitrogen-filled glove box, to an oven-dried 8 mL screw-capvial equipped with a magnetic stir bar were added NiBr2·3H2O(2.73 mg, 0.010 mmol, 5 mol%), L1 (2.55 mg, 0.012 mmol, 6mol%), CsF (60.8 mg, 0.40 mmol, 2.0 equiv), and 0.40 mL anhydrousTHF. The mixture was stirred for 5 min, at which timePMHS (30 L, 0.50 mmol, 2.5 equiv) was added, and the stirringwas continued for another 5 min at r.t. Styrene (1a, 31.2 mg, 0.30mmol, 1.5 equiv) and <strong>[66107-29-7]4-methoxyphenyl trifluoromethanesulfonate</strong>(2a, 51.2 mg, 0.20 mmol, 1.0 equiv) were added to the resultingmixture in this order. The tube was sealed with a Teflon-linedscrew cap, removed from the glove box and stirred at 25 C for upto 24 h. The reaction was quenched upon the addition of H2O,and the mixture was extracted with EtOAc (3 ×). The organiclayer was concentrated to give the crude product. n-Dodecane(20 L) was added as an internal standard for GC analysis. Theproduct was purified by chromatography on silica gel for eachsubstrate. The crude material was purified by flash column chromatography(PE-EtOAc = 100:1) to provide the title compound asa white solid in 85% yield (36.0 mg). The analytical data are consistentwith values reported in the literature.10e