[ CAS No. 68716-52-9 ] {[proInfo.proName]}

Name: 68716-52-9|4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane|98%
Brand: Ambeed
SKU: A531829
Price: 5.0 USD
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Quality Control of [ 68716-52-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 68716-52-9 ]

Product Details of [ 68716-52-9 ]

CAS No. :	68716-52-9	MDL No. :	MFCD05663869
Formula :	C₁₆H₁₉BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WQGRAXGAXSNSDL-UHFFFAOYSA-N
M.W :	254.13	Pubchem ID :	2760174
Synonyms :

Safety of [ 68716-52-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 68716-52-9 ]

* 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.

Downstream synthetic route of [ 68716-52-9 ]

[ 68716-52-9 ] Synthesis Path-Downstream 1~88

1
[ 90-11-9 ]
[ 25015-63-8 ]
[ 68716-52-9 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 6458 - 6459

2
[ 90-14-2 ]
[ 25015-63-8 ]
[ 91-20-3 ]
[ 68716-52-9 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 164 - 168
[2]Organic Letters,2014,vol. 16,p. 2366 - 2369
[3]Journal of Organic Chemistry,1997,vol. 62,p. 6458 - 6459
[4]Journal of Organic Chemistry,2000,vol. 65,p. 164 - 168

3
[ 106-37-6 ]
[ 68716-52-9 ]
[ 605-02-7 ]
[ 64065-97-0 ]

Reference： [1]European Journal of Organic Chemistry,1998,p. 701 - 709

4
[ 68716-52-9 ]
[ 207612-71-3 ]
4,4'-bis(1-naphthyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,1998,p. 701 - 709

5
[ 90-11-9 ]
[ 25015-63-8 ]
[ 91-20-3 ]
[ 68716-52-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2366 - 2369
[2]Journal of Organic Chemistry,2000,vol. 65,p. 164 - 168

6
[ 99747-74-7 ]
[ 25015-63-8 ]
[ 91-20-3 ]
[ 68716-52-9 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 164 - 168

7
[ 76-09-5 ]
[ 90-14-2 ]
[ 91-20-3 ]
[ 68716-52-9 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 164 - 168

8
[ 68716-52-9 ]
5-Bromo-6,8-dimethoxy-trans-1,3-dimethylisochromane [ No CAS ]
6,8-Dimethoxy-trans-1,3-dimethylisochroman [ No CAS ]
6,7-Dimethoxy-trans-1,3-dimethyl-5-(1-naphthyl)isochromane [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 799 - 811

9
[ 28912-93-8 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 8683 - 8686
[2]ChemSusChem,2020,vol. 13,p. 1715 - 1719
[3]ChemistryOpen,2017,vol. 6,p. 345 - 349
[4]Chemical Communications,2019,vol. 55,p. 6201 - 6204

10
[ 105-36-2 ]
[ 68716-52-9 ]
[ 2122-70-5 ]

Reference： [1]Chemical Communications,2001,p. 669 - 670

11
[ 141-12-8 ]
[ 68716-52-9 ]
1-((Z)-3,7-Dimethyl-octa-2,6-dienyl)-naphthalene [ No CAS ]
(E)-1-(3,7-dimethylocta-2,6-dienyl)naphthalene [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4311 - 4314

12
[ 105-87-3 ]
[ 68716-52-9 ]
1-((Z)-3,7-Dimethyl-octa-2,6-dienyl)-naphthalene [ No CAS ]
(E)-1-(3,7-dimethylocta-2,6-dienyl)naphthalene [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4311 - 4314

13
[ 21040-45-9 ]
[ 68716-52-9 ]
[ 5751-29-1 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4311 - 4314

14
[ 25240-59-9 ]
[ 99747-74-7 ]
[ 68716-52-9 ]

Reference： [1]Synthesis,2005,p. 547 - 550

15
[ 68716-52-9 ]
[ 90-11-9 ]

Reference： [1]Synthesis,2005,p. 547 - 550

16
[ 626-05-1 ]
[ 68716-52-9 ]
[ 862776-61-2 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 1897 - 1902
[2]Organometallics,2019,vol. 38,p. 2963 - 2971

17
[ 76-09-5 ]
[ 13922-41-3 ]
[ 68716-52-9 ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2918 - 2926
[2]Journal of the American Chemical Society,2013,vol. 135,p. 2552 - 2559
[3]Organic Letters,2015,vol. 17,p. 3086 - 3089
[4]Journal of the American Chemical Society,2020,vol. 142,p. 11647 - 11652

18
[ 75-09-2 ]
[ 108-24-7 ]
[ 68716-52-9 ]
[ 867182-10-3 ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2918 - 2926

19
6-bromo-6'-[(R)-2,2'-dimethoxy-1,1'-binaphthyl-6-]-2,2'-bipyridine [ No CAS ]
[ 68716-52-9 ]
6-[(R)-2,2'-dimethoxy-1,1'-binaphthyl-6-]-6'-(1-naphthyl)-2,2'-bipyridine [ No CAS ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 1277 - 1284

20
[ 90-14-2 ]
[ 25015-63-8 ]
[ 68716-52-9 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 261 - 263

21
[ 18013-97-3 ]
[ 68716-52-9 ]
[ 913175-30-1 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5029 - 5032

22
[ 1005495-05-5 ]
[ 1005495-06-6 ]
[ 68716-52-9 ]
C₄₁H₂₅N [ No CAS ]
C₄₁H₂₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 2h;Heating / reflux;	<Example 5> [Method of producing Exemplified Compound No. 1540]; <n="155"/> <n="156"/>Under a nitrogen atmosphere, 0.50 g (1.03 iraalphaol) of the mixture of Intermediate Compounds 4 and 5, 0.19 g (1.10 mmol) of 4, 4, 5, 5-tetramethyl-2- (naphthalen-1- - yl) -1, 3, 2-dioxaborolane, and 0.06 g (0.05 mmol) of tetrakistriphenylphosphinepalladium were suspended in a mixed solvent of 25 mL of toluene, 13 mL of ethanol, and 10 mL of a 10% aqueous solution of sodium carbonate. The resultant solution was stirred under heat and ? reflux for 2 hours, and the disappearance of Intermediate Compounds 4 and 5 was observed. After that, the resultant was cooled to room temperature, and water was added to the resultant to stop the reaction. An organic layer, was separated, and was then washed with water twice. After that, the solvent was removed by distillation. The resultant residue was purified by- silica gel column chromatography (toluene : ethyl acetate = 10 : 1), whereby 0.47betag of the mixture of Exemplified Compounds 1540 containing Exemplified Compounds 1540-1 and 1540-2 at a composition ratio of 1 : 1 was obtained.NMR measurement identified the structure, of the compound (FIG. 10) .The PL spectrum of a solution (1.0 x lO"5 mol/L) of Exemplified Compound 1540 in toluene was measured. As a result, a blue light emission spectrum having a light emission peak at 434 nm, a half width of 62 nm, and an excellent color purity was shown (FIG. 16) .

Reference： [1]Patent: WO2008/16166,2008,A1 .Location in patent: Page/Page column 153-156

23
[ 1011472-05-1 ]
[ 68716-52-9 ]
[ 1011472-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 160℃; for 0.166667h;Microwave irradiation;	to a solution of LG2-87 (25 mg, 0.076 mmol), 2-(l- naphthylene)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (39 mg, 0.152 mmol, 2.0 equiv.), and Tetrakis(triphenylphosphine)-palladium(0) (11 mg, 0.0096 mmol) in THF (1.0 ml) was added 0.5 ml of aqueous 1 N K2CO3 solution. The resultant mixture was heated at 160 0C under microwave irradiation for 10 min. The mixture was diluted with EtOAc (10 ml), and the organic phase was separated out. After removal of solvent, the residue was subjected to flash column chromatography on silica gel (elution with hexane-EtOAc) to yield LG2-89 as a white foam (33 mg). ESI-MS: m/z 376 (M+l); IH NMR (600 MHz, CDC13): delta 8.23 (IH, s), 8.18 (IH, br .s), 8.11 (IH, s), 8.02 (IH, br. s), 7.98 (IH, d, J= 7.8 Hz), 7.73 (IH, s), 7.62 (3H, m), 7.57 (IH, t, J= 7.2 Hz), 7.52 (IH, d, J= 8.4 Hz), 7.49 (IH, t, J= 7.8 Hz), 7.42 (IH, d, J= 9.0 Hz), 7.39 (IH, d, J= 4.2 Hz), 7.23 (IH, s), 7.13 (IH, d, J= 4.2 Hz), 6.59 (IH, s); 13C NMR (150.9 MHz, CDC13): delta 147.36, 133.91, 133.84, 132.91, 132.22, 131.98, 131.78,HOU03:1125151 <n="23"/>129.94, 129.10, 128.70, 128.63, 128.32, 127.13, 126.58, 126.51, 125.61, 125.49, 125.20, 124.93, 117.03, 112.68, 111.27, 109.27, 103.01.

Reference： [1]Patent: WO2008/30795,2008,A2 .Location in patent: Page/Page column 21-22

24
[ 3240-34-4 ]
[ 68716-52-9 ]
naphthalen-1-yl(phenyl)iodonium tetrafluoroborate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2007,p. 5353 - 5363

25
[ 68716-52-9 ]
[ 867182-02-3 ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2918 - 2926

26
[ 68716-52-9 ]
N-[(4-methyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-1-yl-methyl]-acetamide [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2918 - 2926

27
[ 68716-52-9 ]
N-[(4-tert-butyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-1-yl-methyl]-acetamide [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2918 - 2926

28
[ 68716-52-9 ]
(S)-3,3'-di[2-(6-(1-naphthyl)pyridyl)]-2,2'-dihydroxy-1,1'-binaphthyl [ No CAS ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 1897 - 1902

29
[ 68716-52-9 ]
C₅₄H₄₀N₂O₄ [ No CAS ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 1897 - 1902

30
[ 90-15-3 ]
[ 68716-52-9 ]

Reference： [1]Synthesis,2005,p. 547 - 550
[2]Journal of the American Chemical Society,2015,vol. 137,p. 1593 - 1600
[3]Organic Letters,2020,vol. 22,p. 5582 - 5588

31
[ 90-11-9 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Yield	Reaction Conditions	Operation in experiment
92.7%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In tetrahydrofuran; at 80℃; for 5h;Inert atmosphere;	In a 250 mL three-necked flask, nitrogen gas is introduced.Add 0.02 mol of 1-bromonaphthalene dissolved in 100 ml of tetrahydrofuran (THF), and then add 0.024 mol of bis(pinacolyl)diboron, 0.0002 mol of (1,1'-bis(diphenylphosphino)ferrocene) dichloride. Palladium (II) and 0.05 mol of potassium acetate were added, the mixture was stirred, and the mixed solution of the above reactants was heated and refluxed at a reaction temperature of 80 C for 5 hours; after the reaction was completed, 100 ml of water was added thereto, and the mixture was filtered and dried in a vacuum oven. Dry in the middle. The obtained residue was separated and purified on a silica gel column to obtain 4-biphenylboronic acid pinacol ester; HPLC purity: 99.9%, yield: 92.7%.
74%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 120℃; for 12h;	1-bromonaphthalene (50.0 g, 241 mmol), bis (pinacolato) diboron (67.4 g, 266 mmol), KOAc (71 g, 724 mmol),PdCl 2 (dppf) (5.30 g, 7.24 mmol) was dissolved in DMF (1 L) solvent, and refluxed at 120 C. for 12 hours.When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2, and wiped with water.After drying and concentrating the organic layer with MgSO4, the resulting organic material was used with CH2Cl2 and methanol solvent.Recrystallization gave 45.4 g (yield: 74%) of the desired product.
73%	With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In toluene; for 24h;	Sub B (1)-2 (4.14g, 20mmol) was dissolved in 48 mL toluene, bis(pinacolato)diboron (5.58g, 22mmol), Pd (dppf) Cl2 catalyst (0.44g, 0.6mmol), KOAc (5.89 g, was added as 60mmol) the sequence after 24 hours with stirring to synthesize a borate compound, and then the resulting compound was separated through a silica gel column and recrystallized to obtain 3.7g to Sub B-2. (Yield: 73%)

57%

With potassium acetate;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; In dimethyl sulfoxide; at 90℃; for 42h;Product distribution / selectivity;

In air, a vial was charged with Ih (10.2 mg, 0.015 mmol, 3 mol %), bis(pinacolato)diboron (0.1397 g, 0.55 mmol) and KOAc (0.147 g, 1.5 mmol). The vial was sealed and purged with argon. Bromobenzene (52 muL, 0.5 mmol) and 3 mL of DMSO were then added. The resulting mixture was then stirred at 90 C. until the reaction was complete. The product was extracted into ether, separated and dried over MgSO4. The product was purified by column chromatography. Results for various substrate scope and reaction conditions are presented in Table 9.

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 977 - 983
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 7595 - 7600
Angew. Chem.,2017,vol. 129,p. 7703 - 7708,6
[3]Patent: CN110229145,2019,A .Location in patent: Paragraph 0104; 0105; 0106; 0107
[4]ACS Catalysis,2018,vol. 8,p. 4049 - 4054
[5]Journal of the American Chemical Society,2016,vol. 138,p. 2985 - 2988
[6]Journal of the American Chemical Society,2020,vol. 142,p. 2087 - 2092
[7]Journal of the American Chemical Society,2020
[8]Patent: KR2020/37542,2020,A .Location in patent: Paragraph 0525; 0538-0542; 0572-0576
[9]Patent: KR2015/135626,2015,A .Location in patent: Paragraph 0322-0325
[10]Chemistry - An Asian Journal,2019,vol. 14,p. 1754 - 1762
[11]Green Chemistry,2012,vol. 14,p. 661 - 667
[12]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2002 - 2010
[13]Organometallics,2019,vol. 38,p. 3060 - 3073
[14]Journal of Organic Chemistry,2019,vol. 84,p. 10805 - 10813
[15]Organometallics,2019,vol. 38,p. 2963 - 2971
[16]Patent: US2007/73055,2007,A1 .Location in patent: Page/Page column 15; 26
[17]Angewandte Chemie - International Edition,2010,vol. 49,p. 2028 - 2032
[18]Journal of Organic Chemistry,2015,vol. 80,p. 7435 - 7446
[19]Journal of Organic Chemistry,2015,vol. 80,p. 9671 - 9681
[20]Tetrahedron,2018,vol. 74,p. 425 - 432

32
[ 109-04-6 ]
[ 68716-52-9 ]
[ 76759-26-7 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 5381 - 5384
[2]Journal of Organic Chemistry,2009,vol. 74,p. 2718 - 2725

33
[ 61676-62-8 ]
[ 90-11-9 ]
[ 68716-52-9 ]

Yield	Reaction Conditions	Operation in experiment
77%		1-bromo- naphthalene 2.07 g (10 mmol) was dissolved in 30 mL THF , 4 mL of n -butyllithium at -78 ( 2.5M inHexane) was added. After an hour at the same temperature, 22-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2.0 mL (10 mmol) was added . After stirring for 5 hours at room temperature water was added and three times with diethyl ether (30 mL)Washed . After drying the washed diethyl ether layer over MgSO4 followed by drying under reduced pressure the product was obtained and then purified by silica gel columnPurification by intermediate I-1 1.96 g ( yield 77 %) was obtained by chromatography . And the resulting compound is confirmed by LC-MS
77%		1-bromo-naphthalene 2.07 g (10 mmol) to 30 mL THF and then dissolved, n-butyl lithium at -78C mL 4 (2.5M in Hexane) was added. After an hour at the same temperature, 2-isopropoxy-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane(2-isopropoxy-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane) 2.0 mL (10 mmol) was added. After stirring for 5 hours at room temperature water was added and washed three times with diethyl ether (30 mL). After drying the washed diethyl ether layer over MgSO4 dried under reduced pressure to obtain a product, followed by separation by silica gel column chromatography purification Intermediate I-9 1.96 g (yield 77%). The resulting compound was confirmed by LC-MS.

Reference： [1]Organic Letters,2011,vol. 13,p. 3312 - 3315
[2]Chemistry - A European Journal,2014,vol. 20,p. 263 - 271
[3]Journal of Organic Chemistry,2009,vol. 74,p. 2718 - 2725
[4]Patent: KR2015/127023,2015,A .Location in patent: Paragraph 0393-0397
[5]Patent: KR2016/30003,2016,A .Location in patent: Paragraph 0367; 0368; 0369; 0370
[6]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3553 - 3557

34
[ 90-14-2 ]
[ 73183-34-3 ]
[ 94647-81-1 ]
[ 68716-52-9 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 5350 - 5354
Angew. Chem., Int. Ed.,2009,vol. 121,p. 5454 - 5458

35
[ 90-14-2 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Yield	Reaction Conditions	Operation in experiment
32%Chromat.	With copper(II) ferrite; potassium tert-butylate; In N,N-dimethyl-formamide; at 20℃; for 12h;Green chemistry;	General procedure: 4-Iodoanisole (0.813 mmol, 200 mg), bis(pinacolato)diboron (1.219 mmol, 309 mg) were dissolved in 3 mL of dmf followed by copper ferrite nanoparticles (5mol% with respect to 4-iodoanisole) and potassiumtert-butoxide (1.219 mmol, 137 mg) were added to a 10 mLcapped vial and stirred at RT for time indicated. After stirring, the mixture was diluted with diethyl ether and filtered through celite bed. The filtrate was extracted with water (3 times) and the organic phase was dried over anhydrous MgSO4. The crude product was subjected to analyze by GC-MS. The conversion yield is accurately measured based on the consumption of 4-iodoanisole and the side product formed due to protodeiodination.

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 18730 - 18733
[2]Organic Letters,2014,vol. 16,p. 4562 - 4565
[3]Organic Letters,2016,vol. 18,p. 5248 - 5251
[4]Journal of the American Chemical Society,2020
[5]Angewandte Chemie - International Edition,2009,vol. 48,p. 5350 - 5354
Angew. Chem., Int. Ed.,2009,vol. 121,p. 5454 - 5458
[6]Journal of Organic Chemistry,2019,vol. 84,p. 10805 - 10813
[7]European Journal of Organic Chemistry,2013,p. 6263 - 6266
[8]Chinese Journal of Chemistry,2019,vol. 37,p. 347 - 351
[9]Catalysis Communications,2016,vol. 85,p. 61 - 65

36
[ 91-20-3 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 2028 - 2032

37
[ 215313-78-3 ]
[ 68716-52-9 ]
[ 1352088-67-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 143 - 159

38
[ 68716-52-9 ]
potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
[ 91-20-3 ]
[ 604-53-5 ]
[ 26458-04-8 ]
[ 2216-69-5 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 1577 - 1581

39
[ 68716-52-9 ]
potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
[ 604-53-5 ]
[ 26458-04-8 ]
[ 2216-69-5 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 1577 - 1581
[2]Chemistry - A European Journal,2012,vol. 18,p. 1577 - 1581

40
[ 68716-52-9 ]
potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
[ 26458-04-8 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 1577 - 1581

41
[ 68716-52-9 ]
potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
[ 26458-04-8 ]
[ 2216-69-5 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 1577 - 1581
[2]Chemistry - A European Journal,2012,vol. 18,p. 1577 - 1581

42
[ 68716-52-9 ]
potassium (trifluoromethyl)triethoxyborate [ No CAS ]
[ 5328-01-8 ]
[ 26458-04-8 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 1577 - 1581

43
[ 68-12-2 ]
[ 68716-52-9 ]
[ 86-53-3 ]

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

44
[ 1384579-32-1 ]
[ 68716-52-9 ]
[ 1384579-38-7 ]

Yield	Reaction Conditions	Operation in experiment
26%	With 1,8-diazabicyclo[5.4.0]undec-7-ene;bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; In N,N-dimethyl-formamide; at 150℃; for 4h;	(3) Synthesis of exemplified compound XX- 1Reagents and a solvent described below were placed in a reactor .Compound X5 : 1.0 g (1.5 mmol )Compound X6 : 0.55 g (2.2 mmol)DMF: 20 mlBis(dibenzylideneacetone) palladium( 0 ) : 0.84 g (1.5 mmol )l,8-Diazabicyclo[5.4.0]undec-7-ene: 0.44 g (2.9 mmol) Tricyclohexylphosphine : 0.81 g (2.9 mmol)[0105] Next, the reaction solution was heated to 150 C and stirred at this temperature (150 C) for 4 hours. Next, the reaction solution was cooled and then concentrated under reduced pressure to produce a dark-red solid. The resultant solid was purified by column chromatography (developing solvent; toluene : heptane = 1:3) and then recrystallized with chloroform/methanol to produce 247 mg of dark-red exemplified compound XX-1 (yield: 26%).

Reference： [1]Patent: WO2012/93578,2012,A1 .Location in patent: Page/Page column 37

45
[ 1232679-86-5 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4560 - 4563

46
[ 68716-52-9 ]
[ 321-38-0 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 2552 - 2559

47
[ 79-01-6 ]
[ 68716-52-9 ]
[ 83671-21-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3396 - 3400

48
[ 106-38-7 ]
[ 68716-52-9 ]
[ 27331-34-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3553 - 3557

49
[ 1548389-35-0 ]
[ 68716-52-9 ]
[ 1548389-42-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 5h;	3.67 g (10.0 mmol) of Intermediate I-7b (which was produced by substituting a hydrogen of Intermediate I-7a with deuterium), 2.54 g (10.0 mmol) of <strong>[68716-52-9]4,4,5,5,-tetramethyl-2-naphthalen-1-yl-[1,3,2]dioxaborolane</strong>, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.15 g (30.0 mmol) of K2CO3 were dissolved in 50 mL of a mixed solution of THF/H2O (2:1), which was then stirred at about 70 C. for about 5 hours. The reaction solution was cooled to room temperature, followed by extraction three times with 50 mL of water and 50 mL of diethylether. The collected organic phase was dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 3.23 g of Intermediate I-8b (Yield: 78%). This compound was identified using MS/FAB. C30H14D12O: calc. 414.60. found 414.72
78%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 5h;	Intermediate I-7a in intermediates I-7b substituting hydrogen of the methyl group with deuterium of 3.67g (10.0 mmol), 4,4,5,5- tetramethyl-2-naphthalen-l-yl[l, 3,2]dioxaborolane(4,4,5,5-Tetramethyl-2-naphthalen-1-yl- [1,3,2]dioxaborolane) 2.54g (10.0mmol), Pd (PPh3) 4 0.58 g (0.5 mmol) , K2CO3 4.15 g (30.0 mmol) and THF / H2O (2/1, v / v) mixed solution was dissolved in 50 After stirred at 70 C for 5 hours. After cooling the reaction solution to room temperature and extracted three times with diethyl ether and water 50ml . The combined organic layers were dried over magnesium sulfate, and separation of the residue obtained by evaporation of the solvent in jelgwan silica chromatography to yield the intermediate I-8b 3.23g (yield: 78%). The resulting compound was confirmed by MS / FAB. C30H14D12O calculated 414.60, 414.72 measure

Reference： [1]Patent: US2014/27721,2014,A1 .Location in patent: Paragraph 0143; 0144
[2]Patent: KR2016/56315,2016,A .Location in patent: Paragraph 0227; 0228; 0229; 0230

50
[ 1401094-66-3 ]
[ 68716-52-9 ]
[ 1533422-51-3 ]

Yield	Reaction Conditions	Operation in experiment
63%	With Pd(OTf)2(CH3CN)4; sodium hydrogencarbonate; N-acetyl-D-tert-leucine; silver carbonate; p-benzoquinone; In water; dimethyl sulfoxide; tert-butyl alcohol; at 100℃; for 18h;Inert atmosphere; Schlenk technique;	General procedure: In a 50 ml Schlenk tube, starting material 1 (49.8 mg, 0.2 mmol), 4-methoxycarbonylphenylboronic acid pinacol ester (2) (104.8 mg, 0.4 mmol),Pd(OTf)2(MeCN)4 (11.4 mg, 0.02 mmol), Ac-D-tLeu-OH (3) (6.9 mg, 0.04 mmol),NaHCO3 (100.8 mg, 1.2 mmol), Ag2CO3 (110.3 mg, 0.4 mmol) and 1,4-benzoquinone (10.8 mg, 0.1 mmol) were combined. The flask was evacuated and backfilled with N2 three times, before a solution of dimethylsulfoxide (DMSO,6.0 mg, 0.076 mmol), water (20 mg, 1.1 mmol) and t-amyl-OH (1 ml, 0.2 M) was added. The reaction mixture was then stirred at 100 8C for 18 hours. After being allowed to cool to room temperature, the mixture was diluted with a 1:1 mixture of hexanes:ethyl acetate, and filtered through a pad of celite. The filtrate was concentrated in vacuo, and the resulting residue purified by column chromatography using an eluent of hexanes:ethyl acetate. The product, 1b, was obtained as a light-yellow liquid (62.9 mg, 82%).The above procedure to prepare 1b is generally representative for all the products shown in Tables 3 and 4. Any deviations from this protocol are specified in the footnotes of the tables.

Reference： [1]Nature Chemistry,2014,vol. 6,p. 146 - 150

51
[ 73183-34-3 ]
[ 90-13-1 ]
[ 68716-52-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel; In tetrahydrofuran; at 100℃; for 2h;Inert atmosphere; Sealed tube;	Under an argon atmosphere,4.2 mg (0.015 mmol) of dichlorobis (trimethylphosphine) nickel,80.5 mg (0.5 mmol) of 1-chloronaphthalene,152 mg (1.0 mmol) of cesium fluoride,153 mg (0.6 mmol) of 4,4,5,5,4 ', 4', 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of tetrahydrofuran were added and sealed,Followed by stirring at 100 C. for 2 hours. After cooling the reaction vessel to room temperature,1 mL of a saturated aqueous solution of ammonium chloride was added and the mixture was extracted three times with 8 mL of ethyl acetate,The organic phases obtained were combined.The solvent was distilled off under reduced pressure,The residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 16: 4: 0 to 16: 4: 1)101 mg (white solid, yield 80%) of 2- (1-naphthyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was obtained

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 977 - 983
[2]Organic and Biomolecular Chemistry,2014,vol. 12,p. 3604 - 3610
[3]ACS Catalysis,2018,vol. 8,p. 4049 - 4054
[4]Organic Letters,2017,vol. 19,p. 4142 - 4145
[5]Patent: JP5699037,2015,B2 .Location in patent: Paragraph 0119; 0120
[6]Journal of the American Chemical Society,2019,vol. 141,p. 9124 - 9128
[7]ACS Catalysis,2017,vol. 7,p. 3199 - 3203
[8]Journal of the American Chemical Society,2020
[9]ChemCatChem,2016,vol. 8,p. 2317 - 2320
[10]Journal of the American Chemical Society,2020,vol. 142,p. 2087 - 2092
[11]Organic and Biomolecular Chemistry,2019,vol. 17,p. 6601 - 6606
[12]Organometallics,2016,vol. 35,p. 1559 - 1564
[13]Angewandte Chemie - International Edition,2018,vol. 57,p. 10999 - 11003
Angew. Chem.,2018,p. 11165 - 11169,5
[14]RSC Advances,2018,vol. 8,p. 13643 - 13648

52
[ 1610455-49-6 ]
[ 68716-52-9 ]
(1R,2R)-N-(4-cyano-2,3,5,6-tetrafluorophenyl)-1-ethyl-2-(naphthalen-1-yl)cyclobutanecarboxamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 8138 - 8142

53
[ 18014-00-1 ]
[ 68716-52-9 ]
[ 1054613-92-1 ]

Yield	Reaction Conditions	Operation in experiment
86%		Di<strong>[18014-00-1]methyl 2,5-dibromoterephthalate</strong> (3.0 g, 8.53 mmol), 1-naphthaleneboronic acid (3.39 g, 19.73 mmol), toluene (100 mL), potassium carbonate aqueous solution (40 mL, 2M, 80 mmol) and 3 drops of aliquat 336 were added to a 250 mL flask flushed with nitrogen. The mixture was bubbled with nitrogen for 0.5 h, then Pd(PPh3)4 (0.79 g, 0.68 mmol) was added. The mixture was stirred, heated at reflux for 48 h under nitrogen. It was then cooled, diluted with water and extracted with toluene. The organic phase was dried over anhydrous MgSO4 and evaporated to yield a white solid: 3.31 g, 86% yield. 1H NMR (400 MHz, CDCl3, d): 8.06 (s, 2H), 7.95e7.91 (m, 4H), 7.67e7.41 (m, 10H), 3.39 (d, J 4.0 Hz, 6H).

Reference： [1]Polymer,2014,vol. 55,p. 2262 - 2270

54
[ 68716-52-9 ]
[ 1263048-18-5 ]

Reference： [1]Polymer,2014,vol. 55,p. 2262 - 2270

55
[ 68716-52-9 ]
[ 1604784-82-8 ]

Reference： [1]Polymer,2014,vol. 55,p. 2262 - 2270

56
[ 68716-52-9 ]
C₅₂H₇₀O₂ [ No CAS ]

Reference： [1]Polymer,2014,vol. 55,p. 2262 - 2270

57
[ 134-32-7 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: To a solution of arylamine (0.5 mmol, 1.0 equiv) in MeOH(1.0 mL) was added HCl (0.5 mL, 1.5 mmol, 3.0 equiv) followed by H2O (0.5 ml). This mixture was stirred 2 min, and the NaNO2 solution (0.25 mL) was then added. The NaNO2 solution was prepared by dissolving 35 mg of NaNO2 in H2O (0.25 mL). This mixture was stirred 30 minat 0-5 C followed by B2pin2 (2, 381 mg, 1.5 mmol, 3.0equiv) in MeOH (1.0 mL). This mixture was stirred 60 min.H2O (10 mL) was added to the reaction mixture, then extracted with CH2Cl2 (50 mL, 3×). The combined organic layers were washed with sat. NaHCO3, dried over Na2SO4, followed by evaporation, and the crude residue was purified by flash chromatography.
78%		General procedure: An arylamine (50 mmol) was dissolved in 50% hydrofluoroboric acid(17 mL) and water (20 mL). After cooling the reaction mixture to 0 C, a solution of sodium nitrite (3.4 g in 7.5 mL water) was added dropwise to the reaction system (over 5 min). The resulting mixture was stirred for 1h and the precipitate was collected by filtration. It was redissolved in the minimum amount of acetone and then diethyl ether was added to precipitate the aryl diazonium tetrafluoroborate. The product was filtered, washed with diethyl ether and dried under reduced pressure. Borylation of aryldiazonium salts; general procedure The aryldiazonium salt (0.5 mmol) and (Bpin)2 (0.75 mmol) were added to an oven-dried Schlenk tube. The tube was evacuated and backfilled with argon (three times). CH3OH (0.8 mL) was added to this Schlenk tube. The tube was sealed and the mixture was stirred at room temperature (22-25 C) for 36 h. After evaporation of the solvent, the residue was purified by column chromatography to afford the product.The arylboronates were purified by chromatography on a silica column eluting with petroleum ether (boiling range 60-90 C) or a petroleumether/ethyl acetate mixture (ca. 60:1) by volume giving Rf values for the boronates of ca. 0.2-0.3.
68%		General procedure: Aryl amine (10 mmol) was dissolved in a mixture of 5 mL of distilled water and 3.4 mL of 50% hydrofluoroboric acid. After cooling the reaction mixture to 0 C using ice bath and the sodium nitrite (0.69 g in 2 mL distilled water), was added dropwise in 5 min interval of time. The resulting mixture was stirred for 1 h and the precipitate was collected by filtration and redissolved in minimum amount of acetone. Diethylether was added until precipitation of aryl diazonium tetrafluoroborate, which is filtered, washed several times with diethyl ether and dried under vacuum. Typical reaction procedure: General procedure: Diazonium tetrafluoroborate salts (0.5 mmol) and B2pin2 (1.5 mmol) were transferred into an oven-dried tube under air. Then acetone/H2O (2/1, 4 mL) were added into the tube via syringe. The sealed tube was keep at 20 C and stirred for 1-2 h. After the reaction was complete, dichloromethane was added to extract the product and the combined organic solution was dried by Na2SO4. The pure product was isolated after column chromatography on silica gel (petroleum ether/ethyl acetate).

Reference： [1]Synlett,2014,vol. 25,p. 1577 - 1584
[2]Journal of Chemical Research,2018,vol. 42,p. 481 - 485
[3]Tetrahedron Letters,2017,vol. 58,p. 3851 - 3853

58
[ 69214-09-1 ]
[ 68716-52-9 ]
5-(naphthalen-1-yl)imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 1367 - 1374

59
[ 68716-52-9 ]
imidazo[5,1,2-de]naphtho[1,8-ab]quinolizine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 1367 - 1374

60
[ 68716-52-9 ]
dimethyl benzo[de]indolizino[3,4,5-ab]isoquinoline-1,2-dicarboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 1367 - 1374

61
[ 509073-87-4 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 2950 - 2955
[2]Journal of the American Chemical Society,2015,vol. 137,p. 1593 - 1600

62
[ 75264-92-5 ]
[ 68716-52-9 ]
[ 1447204-45-6 ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 4394 - 4397

63
[ 76-09-5 ]
2-B-((N,N-diisopropylamino)-1-naphth-1-yl)-borane [ No CAS ]
[ 68716-52-9 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: In a reaction flask charged with CTA-NTf2 (100 mg) under argon atmosphere were added, in this following order: anhydrous toluene (4 mL), distilled iPr2NH (0.42 mL, 3 mmol), arylbromide (1 mmol),and amine-borane complex (0.3 mL, 2 mmol). The reaction mixture was then heated at 110 C for 16 h. After total consumption of either starting material, the reaction mixture was cooled at -5 C,quenched with anhydrous MeOH (2 mL), and stirred for 1 h at room temperature. All volatiles were removed under vacuum before adding pinacol (153 mg, 1.3 mmol) and Et2O (2 mL), and the mixture was stirred for 4 h at room temperature. Then the reaction mixture was diluted with Et2O (10 mL), and the organic phase was washed first with a solution of HCl (0.1 N, 210 mL), followed by an aqueous solution of CuCl2 (50 g/L, 310 mL), dried over Na2SO4, filtered, and concentrated under vacuum. The crude oil was passed through a pad of silica gel, eluting with Et2O. The resulting filtrate was concentrated under vacuum and eventually purified by flash chromatography if some impurities were present in the residue.

Reference： [1]Tetrahedron,2014,vol. 70,p. 6156 - 6161

64
[ 90-11-9 ]
[ 68716-52-9 ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 6156 - 6161

65
[ 24424-99-5 ]
[ 68716-52-9 ]
[ 66821-79-2 ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 3540 - 3551

66
[ 373-53-5 ]
[ 68716-52-9 ]
[ 55831-10-2 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3086 - 3089

67
[ 53811-50-0 ]
[ 68716-52-9 ]
2,3-dimethoxy-6-naphthalen-1-yl-benzaldehyde [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 7435 - 7446

68
[ 1351445-39-0 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 16796 - 16800

69
[ 86-56-6 ]
[ 68716-52-9 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 16796 - 16800

70
[ 68716-52-9 ]
[ 36793-27-8 ]
7,7,9-trimethyl-9-(naphthalen-1-ylmethyl)-1,4-dioxa-8-azaspiro[4.5]decane [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 15840 - 15844
Angew. Chem.,2015,vol. 127,p. 16066 - 16070,5

71
[ 10075-72-6 ]
[ 73183-34-3 ]
[ 68716-52-9 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 2966 - 2969
[2]Organic Letters,2016,vol. 18,p. 2758 - 2761

72
[ 529-36-2 ]
[ 68716-52-9 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 2758 - 2761
[2]Organic Letters,2016,vol. 18,p. 2966 - 2969

73
[ 10072-09-0 ]
[ 68716-52-9 ]
3-(naphthalen-1-ylmethyl)pyridine [ No CAS ]