Name: 1522-13-0|1,1,3-Triphenylpropargyl alcohol|97%
Brand: Ambeed
SKU: A644865
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1
[ 1522-13-0 ]
[ 849-01-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With La3+-montmorillonite; In ethanol; dichloromethane; at 80℃; for 2h;	The 1, 1, 3-triphenyl-3-propyn-1-ol (284 mg, 1mmol) dissolved in 5mL1, in-methylene chloride 2, adding La3+-montmorillonite (200 mg) and ethanol (5mmol, 0 . 29 ml), stirring and heating, in the 80 C reaction under 2 hours, filtered to remove La3+-polynite, concentrated filtrate, product concentrate column chromatography separation to obtain the 1, 3, 3-triphenyl acrylketone 258 mg, yield 91%;
91.3%	In water; at 85℃; for 9h;Molecular sieve;	Weigh 100 mg of 1,1,3-triphenyl-2-propyn-1-ol and dissolve it at 85 C. Add 100 muL of deionized water, stir for 10 minutes, and slowly add 30 mg of MCM-41 molecular sieve (5). After the addition in minutes, the Meyer-Schuster rearrangement reaction of the following reaction equation was carried out at a temperature of 85 C:After reacting for 9 hours, 5 ml of chemically pure ethyl acetate was added to dissolve the organic matter, and then the molecular sieve was filtered off. The ethyl acetate solution was washed with anhydrous sodium sulfate to remove a small amount of water, filtered, and dried, and then separated by column chromatography to obtain 91.3 mg of product. It was 1,3,3-triphenylpropenone in a yield of 91.3%.
90%	With methyl trifluoromethanesulfonate; In acetonitrile; at 70℃; for 1h;	General procedure: To a 25 mL round-bottomed flask were added 1-phenylprop-2-yn-1-ol (1a; 40 mg, 0.3 mmol), TFE (0.5 mL), and MeOTf (6 muL, 0.06 mmol, 0.2 equiv). Then the flask was immersed in a 70 C preheated oil bathand the mixture was stirred for 1 h. After completion, the solution was removed and the residue was subject to flash chromatography (silica gel) with PE/EtOAc as eluent to afford the desired rearrangement product.

83%

With toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 60℃; for 6h;

General procedure: 1-Phenyl-2-propyn-1-ol (66.08 mg, 0.5 mmol) was added to a suspension of p-toluenesulfonicacid (98%, Alfa Aesar, 28.35 mg, 30 mol%) in dry 1,2-dichloroethane(3.0mL). The stirred solution was heated at 60oC for 1 h. Then, the solvent was removed at reduced pressure and the residue was purified by column chromatography with n-Hex=EtOAc (7=1) as the eluent to give cinnamaldehyde (2a, 55.70 mg, 84%) asa yellow color oil.

Reference： [1]Journal of the Chemical Society. Chemical communications,1989,p. 386 - 387
[2]Inorganic Chemistry,2013,vol. 52,p. 6533 - 6542
[3]Patent: CN105503553,2016,A .Location in patent: Paragraph 0087; 0088; 0089; 0090; 0091; 0092; 0093; 0094
[4]Patent: CN110078611,2019,A .Location in patent: Paragraph 0014-0019
[5]Synthesis,2017,vol. 49,p. 3149 - 3156
[6]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 2594 - 2598
[7]Tetrahedron Letters,2009,vol. 50,p. 4773 - 4776
[8]Organic Letters,2006,vol. 8,p. 4027 - 4029
[9]Synthetic Communications,2014,vol. 44,p. 1924 - 1929
[10]Chemistry - A European Journal,2012,vol. 18,p. 4748 - 4758
[11]Catalysis Letters,2020,vol. 150,p. 2132 - 2139
[12]Journal of the American Chemical Society,2002,vol. 124,p. 15172 - 15173
[13]European Journal of Organic Chemistry,2011,p. 5967 - 5970
[14]Journal of Organic Chemistry,2019,vol. 84,p. 4246 - 4262
[15]Chemische Berichte,1922,vol. 55,p. 817
[16]Chemische Berichte,1922,vol. 55,p. 817
[17]Bulletin de la Societe Chimique de France,1923,vol. <4> 33,p. 935,938
[18]Bulletin de la Societe Chimique de France,1923,vol. <4> 33,p. 935,938
[19]Bulletin de la Societe Chimique de France,1924,vol. <4> 35,p. 1421,1422
[20]Justus Liebigs Annalen der Chemie,1923,vol. 433,p. 257
[21]Chemische Berichte,1922,vol. 55,p. 817
[22]Chemische Berichte,1922,vol. 55,p. 817
[23]Chemische Berichte,1922,vol. 55,p. 817
[24]Journal of the Chemical Society,1924,vol. 125,p. 843
[25]Journal of the Chemical Society,1963,p. 2707 - 2711
[26]Tetrahedron Letters,1996,vol. 37,p. 853 - 856
[27]Chemistry - A European Journal,2010,vol. 16,p. 9555 - 9562
[28]Chemistry - A European Journal,2012,vol. 18,p. 11894 - 11898
[29]Angewandte Chemie - International Edition,2015,vol. 54,p. 5658 - 5661
Angew. Chem.,2015,vol. 127,p. 45750 - 45753
Angewandte Chemie,2015,vol. 127,p. 45750 - 45753
[30]Journal of the American Chemical Society,2016,vol. 138,p. 13408 - 13414
[31]Organic Letters,2018,vol. 20,p. 5573 - 5577

2
[ 1522-13-0 ]
[ 6880-25-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrogen; potassium carbonate; In ethyl acetate; at 20℃; for 72h;	1,1,3-Triphenylprop-2-yn-1-ol (10, 0.586 g, 2.00 mmol) was dissolved in EtOAc (20 mL) and a mixture of Lindlar?s catalyst (0.080 g) and K2CO3 (0.080 g, 0.58 mmol) added to the solution. The reaction flask was purged, filled with H2 gas and the mixture stirred at atmospheric pressure for 72 h at room temperature. The reaction was then filtered and the solvent removed under reduced pressure, and the crude residue was subsequently purified by flash column chromatography [EtOAc:n-hexane(10:90)] to give 11 (0.432 g, 73%) as a white solid. Mpt: 85-87 C (lit. 87-88 C) [45]. 1H NMR (400 MHz): delta (CDCl3): 2.14 (1H, s, OH), 2.61 (4H, s, 2 × CH2) 7.15-7.47 (15H, m). 13C NMR (125 MHz): delta (CDCl3): 30.37, 44.09, 78.33, 125.92, 126.10, 127.04, 128.35, 128.48, 128.53, 142.43, 146.90. HRMS-ESI (+ve): Calculated for C21H19 (M - OH)+ 271.1481, found 271.1480. IR: KBr disc, numax (cm-1): 3553.5 (-OH stretch of tertiary alcohol).

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 54,p. 483 - 498
[2]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1920,vol. 50,p. 23
Chemisches Zentralblatt,1923,vol. 94,p. 1391

3
[ 119-61-9 ]
[ 536-74-3 ]
[ 1522-13-0 ]

Yield	Reaction Conditions	Operation in experiment
99%		General procedure: A flame-dried flask equipped with a magnetic stirrer and 4A molecular sieves was charged with tetrabutylammonium chloride (27.8 mg, 0.1 mmol) and KOH (560 mg, 10 mmol). Then, 3 mL of THF and phenylacetylene 2 (408.6 mg, 0.44 mL, 4 mmol) were added using syringes, respectively. The reaction mixture was stirred at room temperature for 12 h. Subsequently, 2'-acetonaphthone 1a (170.2mg, 1mmol) was added in 1.5 mL of THF and then the resulting mixture was stirred at room temperature for 3 days. Upon completion, the reaction was quenched by aqueous NH4Cl, extracted with ethyl acetate, and dried over anhydrous MgSO4. The organic solvent was evaporated and resulting crude product was purified by flash chromatography on silica gel (ethyl acetate / hexane = 1/40~1/10) to give the desired tertiary propargylic alcohol 3a (223mg, 82%) as yellow oil.
80.2%	With Nd(3+)8Na(1+)10C4H9O(1-)*HO(1-); In dimethyl sulfoxide; at 30℃; for 24h;Inert atmosphere;Catalytic behavior;	he catalyst was added to the dehydration deoxidized reaction flask under argon protectionNdNas [0C (CH3) 3] 1Q (0H)0.04 mmol,Styrene blockLmmol,DibenzeneLmmol and 0.5mL DMS0, at 30 C under the fall stroke response 24 hours,After the completion of the reaction, deionized water was added,The reaction solution was extracted with dichloromethane, Extracted three times, combined with organic phase, organic phase with anhydrousDried sodium sulfate, the solvent was removed and the column chromatography (eluent petroleum ether: ethyl acetate = 16: 1, v / v)Get the target productPhenylethynylbenzyl alcohol as a pale yellow solid in 80.2% yield.
72%		General procedure: To a solution of phenylacetylen (4 mmol) in dry THF (10 mL), n- BuLi solution (4.4 mmol) was added at -78oC. The solution was allowed to warm to 0oC over 1 hour and stirred at 0oC for 30 minutes. Then the solution was cooled to -78oC again and ketone or aldehyde (4.0 mmol) was added. The reaction mixture was allowed to warm to room temperature over 1 hour and stirred at room temperature until the ketone or aldehyde disappeared monitored by TLC. Then the reaction was quenched by saturated NH4Cl solution and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a residue. Finally the residue was purified through column chromatography on silica gel (200-300 mesh) with hexane/EtOAc as eluent to afford the products1o, 1q, and 1r.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2160 - 2163
[2]Organic Letters,2013,vol. 15,p. 5222 - 5225
[3]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4422 - 4428
[4]European Journal of Organic Chemistry,2017,vol. 2017,p. 3381 - 3385
[5]Journal of Chemical Sciences,2014,vol. 126,p. 1081 - 1089
[6]Patent: CN106632434,2017,A .Location in patent: Paragraph 0056-0057
[7]Research on Chemical Intermediates,2013,vol. 39,p. 2391 - 2399
[8]Tetrahedron Letters,2019,vol. 60,p. 2030 - 2034
[9]Journal of Chemical Research,2007,p. 370 - 372
[10]Russian Journal of Organic Chemistry,2007,vol. 43,p. 784 - 786
[11]Monatshefte fur Chemie,1967,vol. 98,p. 1274 - 1309
[12]Journal of the American Chemical Society,1965,vol. 87,p. 5632 - 5637
[13]European Journal of Organic Chemistry,2006,p. 1383 - 1386
[14]Synlett,2005,p. 2219 - 2223
[15]Organic Letters,2006,vol. 8,p. 4027 - 4029
[16]Organic Letters,2009,vol. 11,p. 4990 - 4993
[17]Organic and Biomolecular Chemistry,2010,vol. 8,p. 4016 - 4025
[18]Journal of Organic Chemistry,2010,vol. 75,p. 6290 - 6293
[19]Journal of Organometallic Chemistry,2011,vol. 696,p. 331 - 337
[20]Organic Letters,2011,vol. 13,p. 3553 - 3555
[21]Chemistry - A European Journal,2012,vol. 18,p. 11894 - 11898
[22]Journal of Organic Chemistry,2014,vol. 79,p. 7616 - 7625
[23]Chemistry - A European Journal,2014,vol. 20,p. 12046 - 12050
[24]Journal of the American Chemical Society,2016,vol. 138,p. 13408 - 13414
[25]Journal of the American Chemical Society,2017,vol. 139,p. 6526 - 6529
[26]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2735 - 2740
[27]Tetrahedron Letters,2017,vol. 58,p. 4642 - 4647
[28]Advanced Synthesis and Catalysis,2018,vol. 360,p. 870 - 874
[29]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2796 - 2800
[30]Journal of Organic Chemistry,2018,vol. 83,p. 15043 - 15056
[31]Organic and Biomolecular Chemistry,2019,vol. 17,p. 1924 - 1928
[32]European Journal of Organic Chemistry,2019,vol. 2019,p. 5740 - 5748
[33]Advanced synthesis and catalysis,2020
[34]European Journal of Organic Chemistry,2020

4
[ 1522-13-0 ]
[ 135-19-3 ]
1,3,3-triphenyl-[3H]-naphtho[2,1-b]pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate; In neat (no solvent); for 0.5h;Heating;	General procedure: A mixture of suitable <strong>[1522-13-0]propargylic alcohol</strong> 1a (1.0 mmol) and naphthol 2a (1.2 mmol) was heated at 120oC in presence of Ca(OTf)2/Bu4NPF6 (5/10 mol%) for 2-4.5 h. After completion of reaction(monitored by TLC), the reaction mixture was diluted with water, extracted with EtOAc thrice, thecombined organic layers were washed with brine solution and dried over anhydrous Na2SO4. Solventwas removed under reduced pressure and the crude product was purified by silica gel columnchromatography (3-5 %, EtOAc in pet ether) to obtain the desired product 3a in 81% yield.

Reference： [1]Journal of Chemical Sciences,2014,vol. 126,p. 1081 - 1089
[2]Synthesis,2011,p. 3152 - 3160
[3]Helvetica Chimica Acta,1997,vol. 80,p. 725 - 738
[4]Tetrahedron Letters,2017,vol. 58,p. 4642 - 4647

5
[ 86-56-6 ]
[ 1522-13-0 ]
dimethyl-(4-triphenylpropa-1,2-dienyl-naphthalen-1-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With titanium tetrachloride In dichloromethane at -40℃; for 6h;

Reference： [1]Karunakar, Galla V.; Periasamy, Mariappan [Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7463 - 7466]

7
[ 1522-13-0 ]
[ 815-57-6 ]
3-methyl-3-(1,3,3-triphenylpropa-1,2-dien-1-yl)pentane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With calcium(II) bis(trifluoromethanesulfonyl)imide In 1,2-dichloro-ethane at 25℃; for 2h;
92%	With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 0.25h;
92%	With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In 1,2-dichloro-ethane at 90℃; for 0.666667h;

88%	With calcium(II) bis(trifluoromethanesulfonyl)imide In 1,2-dichloro-ethane at 20℃; for 0.666667h; regiospecific reaction;
80%	In nitromethane at 20℃; for 0.5h;
72%	With toluene-4-sulfonic acid In acetonitrile at 20℃; for 4h;
63%	With [Ir(COD)(SnCl3)Cl(μ-Cl)]2 In 1,2-dichloro-ethane at 80℃; for 5h; Inert atmosphere; regioselective reaction;	4.3. Representative procedure for the propargylation of dibenzoylmethane 2a with 3-phenyl-1-(p-tolylprop)-2-yn-1-ol 4a catalyzed by [Ir(COD)(SnCl₃)Cl(μ-Cl)]₂ General procedure: A 10 mL Schlenk flask equipped with a magnetic bar was charged with [Ir(COD)(SnCl3)Cl(μ-Cl)]2 (0.0025 mmol), dibenzoylmethane 2a (0.38 mmol), 3-phenyl-1-(p-tolylprop)-2-yn-1-ol 4a (0.25 mmol) and 1,2-dichloroethane (1 mL). The flask was degassed, flushed with argon and placed in a constant temperature bath at 80 °C. The reaction was allowed to continue at 80 °C, and monitored by TLC. After completion, solvent was removed under reduced pressure and the mixture was subjected to column chromatography over silica gel (eluent: gradient mixture of EtOAc/pet ether) to afford the propargylated product 5a in 95% isolated yield.

Reference： [1]Yaragorla, Srinivasarao; Latha, Dandugula Sneha; Rajesh, Pallava [Advanced Synthesis and Catalysis, 2021, vol. 363, # 24, p. 5486 - 5492]
[2]Yaragorla, Srinivasarao; Rajesh; Pareek, Abhishek; Kumar, Ankit [Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4422 - 4428]
[3]Yaragorla, Srinivasarao; Rajesh [European Journal of Organic Chemistry, 2019, vol. 2019, # 33, p. 5740 - 5748]
[4]Yaragorla, Srinivasarao; Rajesh [Organic and Biomolecular Chemistry, 2019, vol. 17, # 7, p. 1924 - 1928]
[5]Huang, Wen; Wang, Jialiang; Shen, Quansheng; Zhou, Xigeng [Tetrahedron, 2007, vol. 63, # 47, p. 11636 - 11643]
[6]Sanz, Roberto; Miguel, Delia; Martinez, Alberto; Alvarez-Gutierrez, Julia M.; Rodriguez, Felix [Organic Letters, 2007, vol. 9, # 4, p. 727 - 730]
[7]Location in patent: experimental part Chatterjee, Paresh Nath; Roy, Sujit [Tetrahedron, 2011, vol. 67, # 25, p. 4569 - 4577]

8
[ 1522-13-0 ]
[ 517-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	With methanesulfonyl chloride; triethylamine; In toluene; at 0 - 110℃; for 4.5h;Heating / reflux;	Propargyl alcohol PA-1, (10.0 g, 35 mMole) was dissolved in toluene (70 mL), with slight heating to get complete dissolution, cooled and stirred at 0 C. under a nitrogen atmosphere. To this solution was added triethylamine (NEt3), (4.95 g, 6.3 mL, 49 mMole) and then treated drop-by-drop with methanesulfonyl chloride (CH3SO2Cl), (6.29 g, 4.24 mL 49 mMole), keeping the temperature of the reaction below 10 C. After the addition, the solution was stirred at 0 C. for 15 minutes, at room temperature for 15 minutes and then heated to 110 C. for 4 hours. After this period, the reaction was cooled, diluted with ethyl acetate (100 mL) and washed with 2N-HCl. The organic layer was collected, dried (MgSO4), filtered and concentrated under reduced pressure to an oil. This oil was dissolved in the minimum amount of ether (approx. 40 mL) and treated with the same volume of methanol. The product YD-1, crystallized out. It was filtered off, washed well with methanol and dried.

Reference： [1]Patent: US2006/25642,2006,A1 .Location in patent: Page/Page column 5

9
[ 778-82-5 ]
[ 1522-13-0 ]
[ 1263145-97-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 3215 - 3222

10
[ 1522-13-0 ]
[ 6292-59-7 ]
[ 1264635-99-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1024 - 1027

11
[ 1522-13-0 ]
[ 1576-35-8 ]
[ 25229-62-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With yttrium(III) trifluoromethanesulfonate; In acetonitrile; at 80℃; for 2h;Inert atmosphere;	General procedure: To a solution of <strong>[1522-13-0]propargylic alcohol</strong>s (0.3 mmol) and p-toluenesulfonyl hydrazide (0.6mmol) in CH3CN (2.0 mL) was added Y(OTf)3 (0.06 mmol) under an air atmosphere.The resulting mixture was heated at 80 C for the indicated time. After completion of the reaction, the mixture was cooled to room temperature. The solvent was removed in a vacuum, and the resulting residue was purified on a silica gel column (Petroleumether/EtOAc) to provide the desired alpha,beta-unsaturated hydrazone products 3.

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 6453 - 6456
[2]Synlett,2015,vol. 26,p. 2170 - 2174
[3]Journal of Organic Chemistry,2015,vol. 80,p. 9224 - 9230

12
[ 1270-98-0 ]
[ 1522-13-0 ]
C₂₆H₂₀Cl₂OTi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; In diethyl ether; at -70 - 20℃;	EXAMPLE 2Synthesis of eta5 -cyclopentadienyl(l , 1 ,3-triphenyl-2-propynoxy) titanium dichloride, MET-H MET-H was prepared as follows. Approximately 1.1 g (5 mmol) of eta5- cyclopentadienyl titanium trichloride (MET-A) was dissolved in 30 mL of diethyl ether, and the solution was cooled from -30 to -70 C. A mixture of 1.42 grams (5 mmol) of l, l,3-triphenyl-2-propyn-l-ol and 0.8 mL of dry Ets in 30 mL of diethyl ether was added over 30 min. The reaction mixture was stirred as room temperature overnight. A white solid was removed by centrifuge. A light orange solid was obtained after diethyl ether was removed under vacuum. The resultant product was recrystallized in toluene. Approximately 1.75 g of MET-H were produced; the yield was 80%. FIG. 2 illustrates the XH-NMR analysis of the MET-H product.

Reference： [1]Patent: WO2012/103057,2012,A1 .Location in patent: Page/Page column 64

13
[ 106-44-5 ]
[ 1522-13-0 ]
[ 1397746-30-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 6.5h;	General procedure: p-Cresol 1b (1.0 g, 9.21 mmol), 2-methyl-3-butyn-2-ol 2 (0.77 g, 9.21 mmol, 0.8 mL) and dichloromethane (10 mL) were taken into a 50 mL round-bottomed flask fitted with a condenser and calcium chloride guard tube. To this, BF3·Et2O (0.26 g, 1.8 mmol, 0.2 mL) was added and the mixture was stirred at room temperature for 6 h. After completion of the reaction (TLC), solvent was removed from the mixture under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, n-hexane) to obtain 6-methyl-2,2-dimethyl-2H-chromene 3b (1.34 g, 84%) as a colorless oil,

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5275 - 5279

14
[ 1522-13-0 ]
[ 1593-60-8 ]
[ 1415035-12-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	With iodine; In dichloromethane; water; at 25℃; for 4h;	General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.

Reference： [1]Tetrahedron,2012,vol. 68,p. 10194 - 10200,7

15
[ 1522-13-0 ]
[ 1593-60-8 ]
[ 1415035-27-6 ]

Yield	Reaction Conditions	Operation in experiment
48%	With N-Bromosuccinimide; ytterbium(III) triflate; In dichloromethane; at 25℃; for 0.5h;	General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) N-tosyl hydroxylamine 2 (0.5 mmol), and NBS (0.6 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at 25 C for 0.5 h. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 6.

Reference： [1]Tetrahedron,2012,vol. 68,p. 10194 - 10200,7

16
[ 1522-13-0 ]
[ 1593-60-8 ]
[ 1415034-97-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With ytterbium(III) triflate; In dichloromethane; at 25℃; for 3h;	General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3.

Reference： [1]Tetrahedron,2012,vol. 68,p. 10194 - 10200,7

17
[ 29906-67-0 ]
[ 1522-13-0 ]
[ 1373883-71-6 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 9510 - 9520

18
[ 1522-13-0 ]
[ 91634-11-6 ]
[ 1373883-74-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With trifluorormethanesulfonic acid In dichloromethane for 12h; Reflux;

Reference： [1]Zhang, Li; Zhu, Yuanxun; Yin, Guangwei; Lu, Ping; Wang, Yanguang [Journal of Organic Chemistry, 2012, vol. 77, # 21, p. 9510 - 9520]

19
[ 53590-47-9 ]
[ 1522-13-0 ]
[ 1616101-45-1 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3592 - 3595

20
[ 53590-58-2 ]
[ 1522-13-0 ]
[ 1616101-46-2 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3592 - 3595

21
[ 20365-21-3 ]
[ 1522-13-0 ]
[ 1620159-82-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 1h;	Methyl 3-oxo-3-phenylpropanedithioate 1a (500 mg, 2.38mmol), <strong>[1522-13-0]1,1,3-triphenylprop-2-yn-1-ol</strong> 2a, (812mg, 2.85mmol) and 5 ml dichloromethane were taken in a 50ml round bottom flask and to this mixture, BF3OEt2 (0.053 ml, 0.4mmol) was added and stirred at room temperature for 1 h. After completion of the reaction (TLC),solvent was removed and the crude product was purified by normal column chromatography (silica gel 60-120mesh, ethyl acetate/hexane = 1:20) to obtain 2-(methylthio)-4,4,6-triphenyl-4H-thiopyran-3-yl)(phenyl)methanone 3a, as a white solid (1.10 g, 95%, mp 162-164 C) which was characterized by the following spectral data: 1H NMR (300 MHz, CDCl3): d = 7.65-7.61 (m, 4H), 7.41-7.36 (m, 4H), 7.29-7.25 (m, 6H), 7.17-7.08 (m, 6H), 6.73 (s, 1H), 2.28 (s, 3H); 13C NMR (75 MHz, CDCl3): d = 194.8, 144.2, 137.3, 136.9, 136.8, 134.7, 132.9, 132.5,129.3, 128.9, 128.8, 128.6, 128.2, 127.8, 127.6, 126.7, 126.6, 57.8, 18.1 ; IR (KBr): nu3053, 2920, 1648, 1594, 1545, 1490, 1260, 750, 693 cm1; MS (ESI) 477 (M+H).ESI-HRMS obtained for C31H25OS2 (M+H) = 477.1332 (calculated: 477.1341).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 4382 - 4385

22
[ 1522-13-0 ]
[ 83392-36-3 ]
[ 1620159-86-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 1h;	General procedure: Methyl 3-oxo-3-phenylpropanedithioate 1a (500 mg, 2.38 mmol), <strong>[1522-13-0]1,1,3-triphenylprop-2-yn-1-ol</strong> 2a (812 mg, 2.85mmol) and 5ml dichloromethane were taken into a 50 ml round bottom flask. To this BF3.OEt2 (0.053 ml, 0.4 mmol) was added and stirred at room temperature for 1 hour. After completion of the reaction (TLC), solvent was removed and the crude product was purified by normal column chromatography(silica gel 60-120 mesh, ethyl acetate/hexane = 1:20) to obtain 2-(methylthio)-4,4,6-triphenyl-4H-thiopyran-3-yl)(phenyl)methanone 3a as a white solid (1.10 g, 95%, m.p. 162-164 C)

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 4382 - 4385

23
[ 1522-13-0 ]
[ 213468-59-8 ]
[ 1620159-90-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 1.5h;	General procedure: Methyl 3-oxo-3-phenylpropanedithioate 1a (500 mg, 2.38 mmol), <strong>[1522-13-0]1,1,3-triphenylprop-2-yn-1-ol</strong> 2a (812 mg, 2.85mmol) and 5ml dichloromethane were taken into a 50 ml round bottom flask. To this BF3.OEt2 (0.053 ml, 0.4 mmol) was added and stirred at room temperature for 1 hour. After completion of the reaction (TLC), solvent was removed and the crude product was purified by normal column chromatography(silica gel 60-120 mesh, ethyl acetate/hexane = 1:20) to obtain 2-(methylthio)-4,4,6-triphenyl-4H-thiopyran-3-yl)(phenyl)methanone 3a as a white solid (1.10 g, 95%, m.p. 162-164 C)

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 4382 - 4385

24
[ 72789-93-6 ]
[ 1522-13-0 ]
[ 1620159-94-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 1.5h;	General procedure: Methyl 3-oxo-3-phenylpropanedithioate 1a (500 mg, 2.38 mmol), <strong>[1522-13-0]1,1,3-triphenylprop-2-yn-1-ol</strong> 2a (812 mg, 2.85mmol) and 5ml dichloromethane were taken into a 50 ml round bottom flask. To this BF3.OEt2 (0.053 ml, 0.4 mmol) was added and stirred at room temperature for 1 hour. After completion of the reaction (TLC), solvent was removed and the crude product was purified by normal column chromatography(silica gel 60-120 mesh, ethyl acetate/hexane = 1:20) to obtain 2-(methylthio)-4,4,6-triphenyl-4H-thiopyran-3-yl)(phenyl)methanone 3a as a white solid (1.10 g, 95%, m.p. 162-164 C)

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 4382 - 4385

25
[ 5616-55-7 ]
[ 1522-13-0 ]
5,6,10b-triphenyl-2,3,5,10b-tetrahydroindeno[1,2-e][1,4]dithiepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With indium(III) chloride In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere; diastereoselective reaction;

Reference： [1]Muthusamy, Sengodagounder; Sivaguru, Manickasamy; Suresh, Eringathodi [Chemical Communications, 2015, vol. 51, # 4, p. 707 - 710]

26
[ 1522-13-0 ]
[ 22179-72-2 ]
C₂₈H₂₀FNS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With 5 wtpercent H-USY zeolite In 1,2-dichloro-ethane at 100℃; for 75h;

Reference： [1]Cabrero-Antonino, Jose R.; Leyva-Prez, Antonio; Corma, Avelino [Angewandte Chemie - International Edition, 2015, vol. 54, # 19, p. 5658 - 5661][Angew. Chem., 2015, vol. 127, # 19, p. 45750 - 45753][Angewandte Chemie, 2015, vol. 127, # 19, p. 45750 - 45753]

27
[ 1522-13-0 ]
[ 1950-68-1 ]
(3-((4-methoxyphenyl)sulfonyl)propa-1,2-diene-1,1,3-triyl)tribenzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 9224 - 9230

28
[ 1522-13-0 ]
[ 5906-98-9 ]
(3-((2-chlorophenyl)sulfonyl)propa-1,2-diene-1,1,3-triyl)tribenzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 9224 - 9230

29
[ 1522-13-0 ]
[ 1028432-04-3 ]
N-((tert-butyldimethylsilyl)oxy)-4-methyl-N-(1,3,3-triphenylpropa-1,2-dien-1-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;

Reference： [1]Tanimoto, Hiroki; Yokoyama, Keiichi; Mizutani, Yusuke; Shitaoka, Takashi; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi [Journal of Organic Chemistry, 2016, vol. 81, # 2, p. 559 - 574]

30
[ 1522-13-0 ]
[ 1028432-04-3 ]
1,3,3-triphenyl-2-tosylprop-2-en-1-one oxime [ No CAS ]
3,5,5-triphenyl-4-tosyl-4,5-dihydroisoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

Reference： [1]Tanimoto, Hiroki; Yokoyama, Keiichi; Mizutani, Yusuke; Shitaoka, Takashi; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi [Journal of Organic Chemistry, 2016, vol. 81, # 2, p. 559 - 574]

31
[ 1522-13-0 ]
[ 100956-66-9 ]
6,7-dimethoxy-2,2,4-triphenyl-1-tosyl-1,2-dihydroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With iron(III) chloride hexahydrate In 1,2-dichloro-ethane for 1h; Reflux;

Reference： [1]Shao, Min; Wu, Yunjun; Feng, Zhijun; Gu, Xiaoxia; Wang, Shaoyin [Organic and Biomolecular Chemistry, 2016, vol. 14, # 8, p. 2515 - 2521]

32
[ 1522-13-0 ]
[ 95060-80-3 ]
C₃₆H₂₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With iodine; In 1,2-dichloro-ethane; at 20℃; for 3h;	General procedure: To a solution of isatin hydrazone (1 mmol) and propargyl alcohol (1.2 mmol) in dry DCE (10 mL) was added 1 or 2.5 equiv of iodine. The reaction mixture was stirred at room temperature under an air atmosphere and monitored by TLC until the disappearance of starting materials. After the appropriate period, the reaction mixture was diluted with DCM (10 mL) and water (15 mL). The organic phase was separated and the aqueous layer washed with DCM (10 mL). Concentration of combined organic layers under reduced pressure afforded the crude product, which was purified by column chromatography using silica gel to afford the corresponding unsymmetrical azines.