Name: 1129-65-3|1-Phenyl-1-hexyne|98%
Brand: Ambeed
SKU: A929993
Price: 9.0 USD
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1
[ 80-44-4 ]
[ 1004-22-4 ]
[ 1129-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	With paraffin oil at 110℃;

Reference： [1]Truchet [Annales de Chimie (Cachan, France), 1931, vol. <10>16, p. 396][Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1930, vol. 191, p. 855]

2
[ 778-28-9 ]
[ 1004-22-4 ]
[ 1129-65-3 ]

Reference： [1]Journal of the American Chemical Society,1938,vol. 60,p. 1882
[2]Bulletin of the Chemical Society of Japan,1974,vol. 47,p. 2663 - 2671

3
[ 1129-65-3 ]
[ 63318-13-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; hydrogenchloride; N-iodo-succinimide In dichloromethane; water at 35℃; for 12h;	3. General procedure for the preparation of 3a-3m General procedure: To a CH2Cl2 solution (3 mL) of Alkyne 1 ( 0.2 mmol, 1eq), N-iodosuccinimide (54 mg, 0.24 mmol, 1.2 eq) and pyridine (1.6 mg, 0.02 mmol, 0.1 eq) in a glass tube, was added dropwise 37 % HCl aqueous solution (25 μL, 0.3 mmol, 1.5 eq). The reaction was then stirred at 35 °C for 12 h with TLC monitoring. After the completion of the reaction, concentration of the reaction mixture, followed by purification via flash chromatography over SiO2 (petroleum to petroleum/ethyl acetate = 100/1 as the eluted solvent) afforded 3a-3m.
	With iodine; copper dichloride In acetonitrile

Reference： [1]Lei, Ya-Ru; Liang, Jia-Ying; Wang, Yu-Jiang; Chen, Zili [Tetrahedron Letters, 2021, vol. 70]
[2]Uemura,S. et al. [Journal of the Chemical Society. Perkin transactions I, 1977, p. 676 - 680]

4
[ 542-69-8 ]
[ 536-74-3 ]
[ 1129-65-3 ]

Yield	Reaction Conditions	Operation in experiment
48%		To an anhydrous THF solution (35 mL) ofphenylacetylene (0.51g, 5 mmol) was added 3.9 mL n-BuLi (,10.5mmol, 2.7 Msolution in hexane) dropwise within 30 min under N2 atmosphere at -20C. 30 minlater, n-BuI (1.93 g, 10.5 mmol) was added and the mixture was stirred for anadditional 30 min at -20C. The reaction temperature was raised to 25C andremained for 30 minutes. The reaction mixture was extracted with CH2Cl2, washedwith aqueous NH4Cl, brine, and dried over Na2SO4. After filtration, the solvents wereevaporated. The crude product was subjected to column chromatography (SiO2, eluent:petroleum ether) to give 0.38 g of 2f as a colorless oil in 48.0% yield.1H NMR (400MHz, CDCl3): 7.38-7.40 (m, 2H), 7.23 - 7.26 (m, 3H), 2.38-2.42 (m, 2H), 1.57 -1.61 (m, 2H), 1.47 - 1.51 (m, 2H), 0.93-0.97 (m, 3H).
48%		To an anhydrous THF solution (35 mL) of phenylacetylene (0.51 g, 5 mmol) wasadded 3.9 mL n-BuLi (10.5 mmol, 2.7 M solution in hexane) dropwise within 30 minat -20C under N2 atmosphere. 30 minutes later, n-BuI (1.93 g, 10.5 mmol) was addedand the mixture was stirred for an additional 30 min at -20 C. The reactiontemperature was raised to 25 C and remained for 30 minutes. The reaction mixturewas extracted with CH2Cl2, washed with aqueous NH4Cl, brine, and dried overNa2SO4. After filtration, the solvents were evaporated. The crude product wassubjected to column chromatography (SiO2, petroleum ether) to give

Reference： [1]Synlett,2014,vol. 25,p. 1585 - 1590
[2]Synlett,2015,vol. 26,p. 1991 - 1996
[3]Bulletin de la Societe Chimique de France,1968,p. 3387 - 3394
[4]Organic Letters,2004,vol. 6,p. 1461 - 1463
[5]Journal of the American Chemical Society,2014,vol. 136,p. 8887 - 8890

5
[ 1129-65-3 ]
[ 15325-54-9 ]
[ 1077-16-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In isopropyl alcohol; toluene; at 100℃; under 3800.26 Torr; for 3h;Schlenk technique; Autoclave;	General procedure: In a glove box, a vial was charged with CuCl (2.0mg, 0.020 mmol), a phosphine ligand (0.020 mmol) and toluene (1.00 mL), and the resultingsolution was stirred for 10 min at room temperature. To this vial, LiOtBu (40 mg, 0.50 mmol) andiPrOH (60 mg, 1.0 mmol) were added in this order. After the resulting mixture was stirred for 1 minat room temperature, 1a (160 mg, 1.0 mmol) and toluene (2.0 mL) were added. The vial was placedin an autoclave and the autoclave was taken out of the glove box. N2 in the autoclave was replacedwith H2 by positive pressure of H2. Then, the mixture was stirred at 100 C for 3 h under 5 atm ofH2. After cooling to room temperature, H2 was released and the mixture was diluted with EtOAc.The conversion was determined by GC analysis with n-tridecane (18 mg, 0.10 mmol) as an internalstandard. The resulting solution was filtered through a pad of silica gel and the yields of theproducts were determined by 1H NMR analysis with 1,3,5-trimethoxybenzene as an internalstandard.

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 4926 - 4931
[2]Synthetic Communications,1993,vol. 23,p. 2397 - 2404
[3]Advanced Synthesis and Catalysis,2012,vol. 354,p. 1264 - 1268
[4]Synlett,2015,vol. 26,p. 318 - 322
[5]Angewandte Chemie - International Edition,2015,vol. 54,p. 14321 - 14325
Angew. Chem.,2015,vol. 127,p. 14529 - 14533,5
[6]Chemical Communications,2017,vol. 53,p. 4612 - 4615

6
[ 1129-65-3 ]
[ 1077-16-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With ethanol; (^BQ‑NC^OP)IrHCl; sodium t-butanolate at 60℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;
90%	With Wilkinson's catalyst; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; hydrogen In toluene at 20℃; for 4h;
90.3 % Chromat.	With lithium; Trimethylenediamine In tetrahydrofuran at 60℃; for 0.116667h;

	With hydrogen In hexane ΔH;
	With hydrogen at 20℃; for 16h;
	With hydrogen In toluene at 60℃; for 24h;

Reference： [1]Wang, Yulei; Huang, Zhidao; Leng, Xuebing; Zhu, Huping; Liu, Guixia; Huang, Zheng [Journal of the American Chemical Society, 2018, vol. 140, # 12, p. 4417 - 4429]
[2]Perea-Buceta, Jesus E.; Fernández, Israel; Heikkinen, Sami; Axenov, Kirill; King, Alistair W. T.; Niemi, Teemu; Nieger, Martin; Leskelä, Markku; Repo, Timo [Angewandte Chemie - International Edition, 2015, vol. 54, # 48, p. 14321 - 14325][Angew. Chem., 2015, vol. 127, # 48, p. 14529 - 14533,5]
[3]Kovarova; Streinz [Synthetic Communications, 1993, vol. 23, # 17, p. 2397 - 2404]
[4]Davis, H. Eugene; Allinger, Norman L.; Rogers, Donald W. [Journal of Organic Chemistry, 1985, vol. 50, # 19, p. 3601 - 3604]
[5]Burk; Gerlach; Semmeril [Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 8933 - 8939]
[6]Kaeffer, Nicolas; Liu, Hsueh-Ju; Lo, Hung-Kun; Fedorov, Alexey; Copéret, Christophe [Chemical Science, 2018, vol. 9, # 24, p. 5366 - 5371]

7
[ 1129-65-3 ]
[ 33720-29-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium periodate; sulfuric acid; ruthenium-carbon composite; In water; acetonitrile;Green chemistry;	At room temperature, 0.06 g of Ru/C (containing 0.03 mmol) catalyst was added to the reaction flask, then sodium periodate 1.398 g (6.6 mmol) was added, and 24 mL of 3:1 volume ratio of CH3CN/H2O was added, followed by adding 0.12 g (1.2 mmol) H2SO4. With stirring and dissolution, 0.354 g (3 mmol) of phenylhexyne (I-7) was added to the reaction flask, the temperature was maintained at about 25C, the reaction was stirred for 30 minutes, the reaction was monitored by TLC, and the reaction of starting material (I-7) was complete. The same procedure as in Example 1 was followed to give 0.57 g of 1-phenylhexanedione (II-7, Rf=0.5) as a white solid with a yield of 100%.
92%	With C25H21ClN5Pd(1+)*Cl(1-); silver nitrate; In 1,4-dioxane; water; at 90℃; for 14h;	General procedure: To a solution of 1,2-diphenylethyne (5a) (500mg, 2.808mmol) in 1,4-dioxane, water (20mL:5mL v/v), complex 3a (63mg, 0.112mmol, 4mol%), AgNO3 (38mg, 0.224mmol, 8mol%) were added and the reaction mixture was stirred at 90C, the progress of the reaction was monitored by TLC. After 19h the reaction mixture was cooled to room temperature, diluted with water and extracted with CH2Cl2. The separated organic layer was dried over Na2SO4, concentrated under vacuum. The residue was subjected to silica gel column chromatography by using hexane/EtOAc (9:1, v/v) as eluent to give benzil (6a) (551mg, 2.623mmol) as a yellow solid in 93% yield. Similarly to a solution of 5b (1000mg, 4.48mmol) in 1,4-dioxane, water (40mL:10mL v/v), complex 3a (102mg, 0.179mmol, 61mg, 4mol%), AgNO3 (61mg, 0.358mmol, 8mol%) were added and the reaction mixture was stirred at 90Cfor 28h to give 6b (871mg, 3.415mmol) as a yellow solid in 76% yield. The characterization data for all the 1,2-diketones (6a-l) are given in the supporting information
32%	With iron(III) chloride; potassium permanganate; In acetone; at -78℃; for 16h;	(Step 1) A mixture of 1-hexyne (0.34 mL, 3.0 mmol), PdCl2(PPh3)2 (47.9 mg, 68.2 mmol), iodobenzene (0.40 mL, 3.6 mmol) in Et3N (30 mL) was stirred at room temperature for 5 min under an argon atmosphere. And then, CuI (6.5 mg, 34 mmol) was added and stirred at the same temperature for 23 h. After the reaction mixture was filtered, the filtrate was washed with water. The mixture was extracted with diethyl ether and washed with brine, before dried over sodium sulfate. The extract was concentrated and the residue was purified by chromatography on silica gel (hexane as eluent) to obtain 1-phenylhex-1-yne (7) (quant.) as a colorless oil. (Step 2) To a solution of 7 (389 mg, 2.46 mmol) in acetone (25 mL) was added KMnO4 (1.9 g, 12 mmol) and FeCl3 (1.1 g, 6.8 mmol) at -78 C and stirred at the same temperature for 16 h. The flask was removed from the cooling bath, and the mixture was filtered to separate precipitated MnO2. The precipitate was washed with dichloromethane. The residue was purified by chromatography on silica gel (hexane/ethyl acetate = 20 : 1 as eluent) to obtain 1k (150 mg, 32% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.98 (2H, ddd, J = 7.2, 1.6, 1.6 Hz, Ph), 7.64 (1H, tt, J = 7.6, 1.6 Hz, Ph), 7.50 (2H, dddd, J = 7.6, 7.2, 1.6, 1.6 Hz, Ph), 2.88 (2H, t, J = 7.4 Hz, COCH2), 1.69 (2H, tt, J = 7.4, 7.2 Hz, COCH2CH2), 1.41 (2H, tq, J = 7.4, 7.2 Hz, COCH2CH2), 0.95 (3H, t, J = 7.4 Hz, CH3); 13C NMR (100 MHz, CDCl3) delta 203.5, 192.6, 134.5, 132.0, 130.1, 128.8, 38.5, 24.9, 22.3, 13.8. Spectral data were consistent with those previously reported in the literature.15

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 13987 - 13990
[2]Patent: CN107935803,2018,A .Location in patent: Paragraph 0051-0054
[3]Journal of Organometallic Chemistry,2018,vol. 860,p. 1 - 8
[4]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1424 - 1428
[5]Tetrahedron Letters,2013,vol. 54,p. 6874 - 6877
[6]Journal of Organic Chemistry,1990,vol. 55,p. 5545 - 5547

8
[ 1129-65-3 ]
[ 14252-32-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tert.-butylhydroperoxide; C₄₈H₇₂O₁₂Rh₂ In ethyl acetate at 40℃; for 24h; Sealed tube;	4.4. General procedure for propargyl oxidation General procedure: A 10 mL tube equipped with a stir bar was charged with sub- strate (2.0 mmol) and Rh 2 (5- t Bu-esp) 2 (1.7 mg, 0.0020 mmol), then sealed by a rubber plug with a needle, followed by the addition of T-HYDRO (1.44 mL, 20 mmol) via syringe. The tube was placed in 40 °C oil bath for 24 h. After cooling to room temperature, sat- urated sodium thiosulfate solution was added to quench the re- action. The mixture was extracted with ethyl acetate (3 ×5 mL) and washed with water (2 ×10 mL). The ethyl acetate layer was separated and dried over Na 2 SO 4 . After evaporation of the solvent, the residue was purified by flash column chromatography (ethyl acetate/hexane) to give the desired products.
80%	With tert.-butylhydroperoxide In water at 40℃; for 2h;
79%	With tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene; potassium carbonate In decane at 0℃; for 16h;	General procedure: To a solution of alkyne 2 (0.5 mmol) in ethyl propionate(1 mL) was added diacetoxyiodobenzene (483 mg, 1.5 mmol) and K2CO3 (35 mg,0.25 mmol) at 0 C. The resultant suspension was vigorously stirred and asolution of tert-butyl hydroperoxide (5.0 M in decane, 400 lL, 2.0 mmol) was added dropwise over 30 min. After completion, the mixture was filtered and the filtrate purified by silica gel chromatography (n-hexane/EtOAc) to give the corresponding alkynoic ketone 3.

62%	With tert.-butylhydroperoxide; toluene-4-sulfonic acid In benzene for 44h; Ambient temperature;
41%	With tert.-butylhydroperoxide In dichloromethane for 21h; Ambient temperature; variety of solvents, effect of reagent, of amount of catalyst and oxidant, examination of further alkynes;

Reference： [1]Ning, Yangbo; Tan, Jiantao; Wang, Zhifan; Wang, Yuanhua [Journal of Organometallic Chemistry, 2021, vol. 954-955]
[2]McLaughlin, Emily C.; Doyle, Michael P. [Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4317 - 4319]
[3]Zhao, Yi; Ng, Angela Wan Ting; Yeung, Ying-Yeung [Tetrahedron Letters, 2014, vol. 55, # 31, p. 4370 - 4372]
[4]Muzart, Jacques; Piva, Olivier [Tetrahedron Letters, 1988, vol. 29, # 19, p. 2321 - 2324]
[5]Muzart, Jacques; Piva, Olivier [Tetrahedron Letters, 1988, vol. 29, # 19, p. 2321 - 2324]

9
[ 108-86-1 ]
[ 693-02-7 ]
[ 1129-65-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium phosphate; C30H37Br2N3Pd(2-); In dimethyl sulfoxide; at 100℃; for 1h;	General procedure: In a typical run, a 4 mL vial equipped with a magnetic stirrer bar was charged with a mixture of aryl halide (1 mmol), alkyne (2 mmol), Pd catalyst (0.01 mmol), K3PO4 (2 mmol), and 2 mL of DMSO in air. The mixture was stirred at 100 C for 1 h, then cooled to room temperature and brine was added into it. The resulting mixture was extracted with ethyl acetate three times, and the crude product was obtained by removing the volatiles. The product was purified by flash column chromatography on silica gel.
55%	With potassium tert-butylate;C43H67Cl2N3Pd; In ethanol; at 20℃; for 12h;Inert atmosphere;	III.2 General Procedure for the Sonogashira ReactionUnder an atmosphere of nitrogen the catalyst of example 15 (2 mol %) was suspended in ethanol (1.00 ml). Bromobenzene (1.00 mmol, 102 mul) and 1-hexyne (1.50 mmol, 173 mul) were added. Finally, KOtBu (1 mmol, dissolved in 1.00 ml ethanol) was added and the mixture was stirred for 12 h at ambient temperature. The solvent used was technical grade ethanol without prior degassing. After this, ammonium chloride (saturated solution, 2.00 ml), ethyl acetate (4.00 ml) and dodecane (1.00 mmol, 226.2 mul) were added. The organic layer was dried with Na2SO4 and analysed by GC. Yield of hex-1-ynylbenzene: 55%.
98%Chromat.	With potassium carbonate; In water; at 20℃; for 3h;	General procedure: An aryl halide (1.0 mmol) and a terminal alkyne (1.2 mmol) were added to a mixture of PS-tazo-Pd(II) (0.001 mmol), K2CO3 (2.0 mmol), and water (3 ml) in a glass flask under vigorous stirring. The mixture was stirred at room temperature for 3 h under aerobic conditions. After completion of the reaction, the mixture was filtered to recover the catalyst. The polymer was washed with water and acetonitrile, vacuum dried, and stored for a new run. After GC analysis, the solvent was removed under vacuum, and the crude product was subjected to silica gel column chromatography using CHCl3-CH3OH (98:2) as eluent to afford the pure product.

96%Chromat.	With piperidine; In water; at 20℃; for 3h;	General procedure: An aryl halide (1.0 mmol) and a terminal alkyne (1.2 mmol) were added to a mixture of PS-dtz-Pd(II) (0.001 mmol), piperidine (2.0 mmol), and water (3 ml) in a glass flask under vigorous stirring. The mixture was stirred at room temperature for 3 h under aerobic conditions. After completion of the reaction, the mixture was filtered to recover the catalyst. The polymer was washed with water and acetonitrile, vacuum dried, and stored for a new run. After GC analysis, the solvent was removed under vacuum, and the crude product was subjected to silica gel column chromatography using CHCl3-CH3OH (97:3) as eluent to afford the pure product.
88%Chromat.	With pyridine; In neat (no solvent); at 20℃; for 3h;	General procedure: Under air atmosphere, around-bottomed flask was charged with an aryl halide (1.0mmol), a terminal alkyne (1.0mmol), a base (1.0mmol), and the catalyst 2 (1mol%). The mixture was stirred at room temperature for 3h under aerobic conditions. After completion of the reaction, the mixture was filtered to recover the catalyst. The polymer was washed with water, methanol, and acetonitrile, vacuum-dried, and stored for a new run. After GC analysis, the solvent was removed under vacuum, and the crude product was subjected to silica gel column chromatography using CHCl3-CH3OH (97:3) as eluent to afford the pure product.
98%Chromat.	With piperidine; In neat (no solvent); at 20℃; for 3h;	General procedure: An aryl halide (1.0mmol) and a terminal alkyne (1.0mmol) was added to a mixture of PS-triazine-Pd(II) (0.001mmol) and base (1mmol) in a glass flask under vigorous stirring. The mixture was stirred at room temperature for 3h under aerobic conditions. Upon completion of the reaction, the reaction mixture was dissolved in chloroform (2mL). The palladium catalyst was separated from the mixture by filtration, washed with acetonitrile (10mL), and reused in the next run. Then to the chloroform solution was added toluene (1.0mmol) as the internal standard for GC analysis. After the analysis, the solvent was removed under vacuum, and the crude product was subjected to silica gel column chromatography using CHCl3-CH3OH (95:5) as eluent to afford the pure product.
97%Chromat.	With 2-methoxyethylamine; at 20℃; for 3h;	General procedure: Aryl halide (1.0 mmol), PVC-triazole-Pd(II) (40 mg, 0.01mmol Pd), base (1.0 mmol), and terminal alkyne (1.0 mmol),were added to a flask, and the reaction mixture was stirred atroom temperature for 3 h under aerobic conditions. Uponcompletion of the reaction, the reaction mixture was dissolvedin chloroform (2 ml). The palladium catalyst wasseparated from the mixture by filtration, washed with acetonitrile(10 ml), and reused in the next run. Then to the chloroformsolution was added toluene (1.0 mmol) as the internalstandard for GC analysis.
88%Chromat.	With triethylamine; In N,N-dimethyl-formamide; at 70℃; for 10h;Inert atmosphere;	General procedure: The typical reaction was carried out with a terminal alkyne (1.0 mmol), an arylhalide (1.0 mmol), Et3N (2.0 mmol), and the catalyst (0.1 g, 0.05 mmol based onCu) in DMF (3.0 mL). The reaction mixture was stirred for 10 h at 70 C under an Ar atmosphere. After completion of the reaction, the mixture was filtered to recover the catalyst. The catalyst was washed with dry toluene, vacuum dried, and stored fora new run. After GC analysis, the solvent was removed under vacuum, and the crudeproduct was subjected to silica gel column chromatography using CHCl3/CH3OH(97:3) as eluent to afford the pure product.
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In acetonitrile; at 75℃; for 8h;Schlenk technique; Inert atmosphere;	General procedure: To a suspension of Ar-Br (10.0 mmol), Pd(PPh3)4 (0.5 mmol), and CuI (1.0 mmol) in degassed CH3CN (15 mL) and Et3N (3 mL) was added alkyne (12.0 mmol) under a nitrogen atmosphere. The resultant mixture was stirred at 75 C for 8 h. The reaction mixture was filtered through a short plug of silica gel with rinsing by EtOAc. The filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography.

Reference： [1],2020,vol. 10,p. 23108 - 23120
[2]Green Chemistry,2011,vol. 13,p. 2408 - 2415
[3]Journal of Organic Chemistry,2004,vol. 69,p. 5428 - 5432
[4]Advanced Synthesis and Catalysis,2005,vol. 347,p. 1295 - 1300
[5]Synlett,2008,p. 3239 - 3241
[6]Tetrahedron,2013,vol. 69,p. 5178 - 5184
[7]New Journal of Chemistry,2006,vol. 30,p. 832 - 837
[8]Dalton Transactions,2012,vol. 41,p. 5020 - 5025
[9]ChemCatChem,2018,vol. 10,p. 758 - 762
[10]Patent: US2012/108819,2012,A1 .Location in patent: Page/Page column 34
[11]Chemistry Letters,2005,vol. 34,p. 1294 - 1295
[12]Synlett,2008,p. 1415 - 1417
[13]Tetrahedron Letters,1995,vol. 36,p. 2401 - 2402
[14]Applied Catalysis A: General,2010,vol. 390,p. 135 - 140
[15]Journal of Organometallic Chemistry,2013,vol. 724,p. 206 - 212
[16]Journal of Molecular Catalysis A: Chemical,2013,vol. 370,p. 152 - 159
[17]Journal of Organometallic Chemistry,2013,vol. 740,p. 78 - 82
[18]Journal of Organometallic Chemistry,2014,vol. 749,p. 405 - 409
[19]Letters in Organic Chemistry,2013,vol. 10,p. 758 - 763
[20]Journal of the Chinese Chemical Society,2014,vol. 61,p. 279 - 284
[21]Research on Chemical Intermediates,2017,vol. 43,p. 7347 - 7363
[22]Tetrahedron,2018,vol. 74,p. 6979 - 6984

10
diphenyliodonium tetrafluoroborate [ No CAS ]
[ 693-02-7 ]
[ 1129-65-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydrogencarbonate In water; acetonitrile for 0.333333h; Ambient temperature;
63%	With copper(l) iodide; sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 20℃; for 0.5h;

Reference： [1]Kang, Suk-Ku; Lee, Hong-Woo; Jang, Su-Bum; Ho, Pil-Su [Chemical Communications, 1996, # 7, p. 835 - 836]
[2]Kang, Suk-Ku; Yoon, Seok-Keun; Kim, Young-Mook [Organic Letters, 2001, vol. 3, # 17, p. 2697 - 2699]

11
[ 591-50-4 ]
[ 693-02-7 ]
[ 1129-65-3 ]

Yield	Reaction Conditions	Operation in experiment
100%		(Step 1) A mixture of 1-hexyne (0.34 mL, 3.0 mmol), PdCl2(PPh3)2 (47.9 mg, 68.2 mmol), iodobenzene (0.40 mL, 3.6 mmol) in Et3N (30 mL) was stirred at room temperature for 5 min under an argon atmosphere. And then, CuI (6.5 mg, 34 mmol) was added and stirred at the same temperature for 23 h. After the reaction mixture was filtered, the filtrate was washed with water. The mixture was extracted with diethyl ether and washed with brine, before dried over sodium sulfate. The extract was concentrated and the residue was purified by chromatography on silica gel (hexane as eluent) to obtain 1-phenylhex-1-yne (7) (quant.) as a colorless oil. (Step 2) To a solution of 7 (389 mg, 2.46 mmol) in acetone (25 mL) was added KMnO4 (1.9 g, 12 mmol) and FeCl3 (1.1 g, 6.8 mmol) at -78 C and stirred at the same temperature for 16 h. The flask was removed from the cooling bath, and the mixture was filtered to separate precipitated MnO2. The precipitate was washed with dichloromethane. The residue was purified by chromatography on silica gel (hexane/ethyl acetate = 20 : 1 as eluent) to obtain 1k (150 mg, 32% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.98 (2H, ddd, J = 7.2, 1.6, 1.6 Hz, Ph), 7.64 (1H, tt, J = 7.6, 1.6 Hz, Ph), 7.50 (2H, dddd, J = 7.6, 7.2, 1.6, 1.6 Hz, Ph), 2.88 (2H, t, J = 7.4 Hz, COCH2), 1.69 (2H, tt, J = 7.4, 7.2 Hz, COCH2CH2), 1.41 (2H, tq, J = 7.4, 7.2 Hz, COCH2CH2), 0.95 (3H, t, J = 7.4 Hz, CH3); 13C NMR (100 MHz, CDCl3) delta 203.5, 192.6, 134.5, 132.0, 130.1, 128.8, 38.5, 24.9, 22.3, 13.8. Spectral data were consistent with those previously reported in the literature.15
95%	With palladium diacetate; potassium carbonate; urea; In ethanol; at 20℃; for 4h;	General procedure: In a 50ml round bottom flask, a mixture of aryl halide (0.5mmol), acetylene (0.75mmol), Pd(OAc)2 (1mol%), Urea (0.25mmol) and K2CO3 (1.5mmol) in EtOH (4ml) were added and stirred at room temperature. After completion (monitored by TLC); the reaction mixture was extracted with ethyl acetate (10ml×3) and the combined organic layer was washed with brine (20ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using n-hexane as eluent to give the corresponding diarylalkyne. The desired products are characterized by comparing 1H, 13C NMR data with authentic samples.
92%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine;Inert atmosphere; Reflux;	Sonogashira coupling reaction: hex-1-yne and iodobenzene (mole ratio: 1.2:1) weredissolved in pre-dried Et2NH at r.t. under N2. Subsequently, Pd(PPh3)4 (5 mol%) andCuI (10 mol%) were then added in the mixture under N2 which was stirred under reflux.The resulting reaction mixture was filtered over silica. The solvent was removed and theresidue was purified by column chromatography on silica to give relevant internalalkyne in 92% yield as colorless liquid (hexane as the eluent).

92%

With tetrabutylammomium bromide; triethylamine; In water; at 70℃; for 8h;

General procedure: An aryl halide (1.0 mmol) and a terminal alkyne (1.2 mmol)were added to a mixture of PS-tet-Pd(II) (0.04 g), Et3N (2.0 mmol),TBAB (1.0 mmol), and H2O (6 mL) in a glass flask under vigorousstirring. The mixture was stirred at 70 C for the appropriate timeunder aerobic conditions. After completion of the reaction, the catalystwas removed by filtration. The polymer was washed withH2O and MeCN, vacuum dried, and stored for a new run. AfterGC analysis, the solvent was removed under vacuum, and thenthe residue was subjected to column chromatography to affordthe pure product. The desired pure products were characterized by NMR, FT-IR, elemental analysis (CHN), and from their meltingpoints.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 6874 - 6877
[2]European Journal of Organic Chemistry,2010,p. 4368 - 4371
[3]Organic Letters,2018,vol. 20,p. 1576 - 1579
[4]Tetrahedron,2007,vol. 63,p. 4642 - 4647
[5]Green Chemistry,2011,vol. 13,p. 2408 - 2415
[6]Journal of Organometallic Chemistry,2009,vol. 694,p. 2555 - 2561
[7]Journal of the American Chemical Society,2010,vol. 132,p. 14070 - 14072
[8]Tetrahedron Letters,2016,vol. 57,p. 914 - 916
[9]Applied Organometallic Chemistry,2017,vol. 31
[10]Organic Letters,2020,vol. 22,p. 3969 - 3973
[11]Journal of Organometallic Chemistry,1998,vol. 570,p. 219 - 224
[12]Synlett,2014,vol. 25,p. 1155 - 1159
[13]Tetrahedron Letters,2014,vol. 55,p. 5298 - 5301
[14]Chemical Communications,2017,vol. 53,p. 4612 - 4615
[15]Advanced Synthesis and Catalysis,2006,vol. 348,p. 133 - 141
[16]Tetrahedron Letters,2008,vol. 49,p. 5286 - 5288
[17]Catalysis Communications,2012,vol. 17,p. 160 - 163
[18]New Journal of Chemistry,2020,vol. 44,p. 1320 - 1325
[19]Applied Organometallic Chemistry,2016,vol. 30,p. 831 - 834
[20]New Journal of Chemistry,2006,vol. 30,p. 832 - 837
[21]Helvetica Chimica Acta,2009,vol. 92,p. 897 - 902
[22]Synthesis,2011,p. 1792 - 1798
[23]Organic Letters,2011,vol. 13,p. 3984 - 3987
[24]Synlett,1999,p. 1645 - 1647
[25]Synthetic Communications,2015,vol. 45,p. 777 - 787
[26]Synlett,2003,p. 1049 - 1051
[27]Synlett,2008,p. 1415 - 1417
[28]Catalysis Communications,2017,vol. 90,p. 31 - 34
[29]Synlett,2007,p. 1843 - 1850
[30]Transition Metal Chemistry,2016,vol. 41,p. 739 - 749
[31]Synlett,2008,p. 3239 - 3241
[32]Tetrahedron Letters,2016,vol. 57,p. 554 - 558
[33]European Journal of Organic Chemistry,2010,p. 6067 - 6071
[34]Synthetic Communications,2010,vol. 40,p. 282 - 288
[35]Tetrahedron,2010,vol. 66,p. 7755 - 7761
[36]Synthesis,2012,vol. 44,p. 1507 - 1510
[37]Synlett,2014,vol. 25,p. 443 - 447
[38]New Journal of Chemistry,2018,vol. 42,p. 11471 - 11479
[39]Dalton Transactions,2017,vol. 46,p. 2439 - 2444
[40]Tetrahedron Letters,2017,vol. 58,p. 2094 - 2097
[41]Angewandte Chemie - International Edition,2018,vol. 57,p. 6090 - 6094
Angew. Chem.,2018,vol. 130,p. 6198 - 6202,5
[42]Journal of Catalysis,2019,vol. 377,p. 183 - 189
[43]Monatshefte fur Chemie,2003,vol. 134,p. 545 - 549
[44]Organic Letters,2019,vol. 21,p. 3755 - 3759
[45]European Journal of Organic Chemistry,2010,p. 1875 - 1884
[46]Synlett,2005,p. 487 - 488
[47]Organic Letters,2007,vol. 9,p. 1045 - 1048
[48]Journal of Organometallic Chemistry,2009,vol. 694,p. 278 - 284
[49]Tetrahedron Letters,2009,vol. 50,p. 1557 - 1559
[50]Tetrahedron Letters,2009,vol. 50,p. 6418 - 6420
[51]Synthetic Communications,2010,vol. 40,p. 179 - 185
[52]Tetrahedron Letters,2010,vol. 51,p. 2758 - 2761
[53]Tetrahedron Letters,2010,vol. 51,p. 5653 - 5656
[54]Applied Catalysis A: General,2010,vol. 390,p. 135 - 140
[55]Applied Organometallic Chemistry,2011,vol. 25,p. 420 - 423
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[68]European Journal of Organic Chemistry,2020,vol. 2020,p. 234 - 240

12
[ 591-50-4 ]
[ 1129-65-3 ]
[ 81740-69-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Stage #2: iodobenzene With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide In tetrahydrofuran; hexane at 20℃;
71%	Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Inert atmosphere; Stage #2: With zinc dibromide In tetrahydrofuran; hexane at -20 - 20℃; Inert atmosphere; Stage #3: iodobenzene With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;
	Yield given; Multistep reaction;

Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran at -20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: With zinc dibromide In tetrahydrofuran at -20 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #3: iodobenzene With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;

Reference： [1]Ma, Shengming; He, Qiwen [Angewandte Chemie - International Edition, 2004, vol. 43, # 8, p. 988 - 990]
[2]Zhao, Jinbo; Liu, Yu; He, Qiwen; Li, Yuxue; Ma, Shengming [Chemistry - A European Journal, 2009, vol. 15, # 42, p. 11361 - 11372]
[3]Ma, Shengming; Zhang, Aibin [Journal of Organic Chemistry, 1998, vol. 63, # 25, p. 9601 - 9604]
[4]Jiang, Quanbin; Li, Huimin; Zhao, Xiaodan [Organic Letters, 2021, vol. 23, # 22, p. 8777 - 8782]

13
[ 624-31-7 ]
[ 1129-65-3 ]
1-phenyl-1-(4'-methylphenyl)-1,2-hexadiene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Stage #2: 4-tolyl iodide With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide In tetrahydrofuran; hexane at 20℃;
79%	Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Inert atmosphere; Stage #2: With zinc dibromide In tetrahydrofuran; hexane at -20 - 20℃; Inert atmosphere; Stage #3: 4-tolyl iodide With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;
	Yield given; Multistep reaction;

Reference： [1]Ma, Shengming; He, Qiwen [Angewandte Chemie - International Edition, 2004, vol. 43, # 8, p. 988 - 990]
[2]Zhao, Jinbo; Liu, Yu; He, Qiwen; Li, Yuxue; Ma, Shengming [Chemistry - A European Journal, 2009, vol. 15, # 42, p. 11361 - 11372]
[3]Ma, Shengming; Zhang, Aibin [Journal of Organic Chemistry, 1998, vol. 63, # 25, p. 9601 - 9604]

14
[ 1129-65-3 ]
[ 90-14-2 ]
1-phenyl-1-(1'-naphthyl)-1,2-hexadiene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Stage #2: 1-Iodonaphthalene With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide In tetrahydrofuran; hexane at 20℃;
63%	Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Inert atmosphere; Stage #2: With zinc dibromide In tetrahydrofuran; hexane at -20 - 20℃; Inert atmosphere; Stage #3: 1-Iodonaphthalene With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;
	Yield given; Multistep reaction;

Reference： [1]Ma, Shengming; He, Qiwen [Angewandte Chemie - International Edition, 2004, vol. 43, # 8, p. 988 - 990]
[2]Zhao, Jinbo; Liu, Yu; He, Qiwen; Li, Yuxue; Ma, Shengming [Chemistry - A European Journal, 2009, vol. 15, # 42, p. 11361 - 11372]
[3]Ma, Shengming; Zhang, Aibin [Journal of Organic Chemistry, 1998, vol. 63, # 25, p. 9601 - 9604]

15
[ 1129-65-3 ]
[ 696-62-8 ]
1-methoxy-4-(1-phenylhexa-1,2-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Stage #2: para-iodoanisole With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide In tetrahydrofuran; hexane at 20℃;
74%	Stage #1: (hex-1-yn-1-yl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Inert atmosphere; Stage #2: With zinc dibromide In tetrahydrofuran; hexane at -20 - 20℃; Inert atmosphere; Stage #3: para-iodoanisole With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; hexane at 20℃; Inert atmosphere; regioselective reaction;
	Yield given; Multistep reaction;

Reference： [1]Ma, Shengming; He, Qiwen [Angewandte Chemie - International Edition, 2004, vol. 43, # 8, p. 988 - 990]
[2]Zhao, Jinbo; Liu, Yu; He, Qiwen; Li, Yuxue; Ma, Shengming [Chemistry - A European Journal, 2009, vol. 15, # 42, p. 11361 - 11372]
[3]Ma, Shengming; Zhang, Aibin [Journal of Organic Chemistry, 1998, vol. 63, # 25, p. 9601 - 9604]

16
[ 1129-65-3 ]
[ 15325-54-9 ]
[ 6111-82-6 ]
[ 1077-16-3 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 7438 - 7446
[2]Angewandte Chemie - International Edition,1999,vol. 38,p. 3715 - 3717
[3]Chemical Communications,2017,vol. 53,p. 4612 - 4615
[4]Chemical Science,2018,vol. 9,p. 5366 - 5371
[5]Dalton Transactions,2019,vol. 48,p. 1161 - 1165

17
[ 1129-65-3 ]
[ 76937-26-3 ]

Yield	Reaction Conditions	Operation in experiment
18%	With water at 220℃; for 4h;

Reference： [1]Doyama, Kazuo; Fujiwara, Keisuke; Joh, Takashi; Maeshima, Kazuo; Takahashi, Shigetoshi [Chemistry Letters, 1988, p. 901 - 904]

18
[ 6214-23-9 ]
[ 1129-65-3 ]
methyl 4-phenylnona-2(E),4,5-trienoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 2287 - 2291

19
[ 1129-65-3 ]
[ 15111-14-5 ]
11-n-butyl-6-phenylisoindolo[2,1-a]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrabutyl-ammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 24h;

Reference： [1]Roesch; Larock [Journal of Organic Chemistry, 2001, vol. 66, # 2, p. 412 - 420]

20
[ 1942-46-7 ]
[ 2170-06-1 ]
[ 1129-65-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With dichloromethane In toluene at 80℃;
55%	With dichloromethane In toluene at 80℃;

Reference： [1]Fuerstner, Alois; Mathes, Christian; Lehmann, Christian W. [Chemistry - A European Journal, 2001, vol. 7, # 24, p. 5299 - 5317]
[2]Fuerstner, Alois; Mathes, Christian [Organic Letters, 2001, vol. 3, # 2, p. 221 - 223]

21
[ 1129-65-3 ]
[ 942-92-7 ]
[ 25870-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium (II) nitrate; 2-amino-phenol In 1,4-dioxane at 120℃; for 5h;
1: 35 %Chromat. 2: 30 %Chromat.	Stage #1: (hex-1-yn-1-yl)benzene With AuP(t-Bu<SUB>)3</SUB>(N-trifluoromethanesulfonyl<SUB>)2</SUB>; glycerol In acetonitrile at 80℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride; water In acetonitrile at 80℃; for 24h; Inert atmosphere;
	With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran; water at 120℃; for 16h; Sealed tube;

	With C₄₇H₄₁AuBF₁₅N₂S In 1,4-dioxane; water at 80℃; for 18h; Overall yield = 100 %; regioselective reaction;
1: 28 %Spectr. 2: 11 %Spectr.	Stage #1: (hex-1-yn-1-yl)benzene With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); Triphenylphosphine oxide In water; toluene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With silver trifluoromethanesulfonate In water; toluene at 50℃; for 1h; Inert atmosphere; regioselective reaction;

Reference： [1]Shimada, Tomohiro; Yamamoto, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 43, p. 12670 - 12671]
[2]Corma, Avelino; Ruiz, Violeta R.; Leyva-Perez, Antonio; Sabater, Maria J. [Advanced Synthesis and Catalysis, 2010, vol. 352, # 10, p. 1701 - 1710]
[3]Fang, Weizhen; Presset, Marc; Guerinot, Amandine; Bour, Christophe; Bezzenine-Lafollee, Sophie; Gandon, Vincent [Chemistry - A European Journal, 2014, vol. 20, # 18, p. 5439 - 5446]
[4]Weerasiri, Kushan C.; Chen, Danmin; Wozniak, Derek I.; Dobereiner, Graham E. [Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 4106 - 4113]
[5]Endo, Naoki; Inoue, Mami; Iwasawa, Tetsuo [European Journal of Organic Chemistry, 2018, vol. 2018, # 9, p. 1136 - 1140]

22
[ 1129-65-3 ]
2,2-dichloro-1-phenyl-1-hexanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With hydrogenchloride; N-chloro-succinimide In 1,4-dioxane; water monomer at 20℃; for 5h;	Representative procedure: 2,2-dichlorooxygenation of alkynol 1a General procedure: A solution of alkynol 1a (95.8 mg, 0.725 mmol, 1.0 equiv) in 3.6 mL of 1,4-dioxane was addedwith NCS (193.3 mg, 1.448 mmol, 2.0 equiv) and 1 M aqueous HCl (0.38 mL, 0.38 mmol, 0.5equiv). The resulted solution was allowed to stir at room temperature until the reaction was judgedcomplete by TLC (typically 5 h). Upon completion, the reaction mixture was diluted with water.The separated aqueous phase was extracted with 3xEtOAc. The combined organic phases werewashed with saturated aqueous NaCl, dried over anhydrous Na2SO4, filtered and concentrated toa crude material. The crude material was purified by SiO2 column chromatography eluting 10%EtOAc-hexane to give the corresponding 2,2-dichloroketone 2a-Cl as a yellow oil (117.2 mg,74%);
	With trichloroisocyanuric acid; water monomer In acetone at 20℃;

Reference： [1]Chaisan, Nattawadee; Ruchirawat, Somsak; Ruengsangtongkul, Sureeporn; Thongsornkleeb, Charnsak; Tummatorn, Jumreang [Synlett, 2022]
[2]Hiegel, Gene A.; Bayne, Christopher D.; Ridley, Brendt [Synthetic Communications, 2003, vol. 33, # 12, p. 1997 - 2002]

23
[ 591-50-4 ]
[ 1129-65-3 ]
1,3-diphenylhexa-1,2-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: (hex-1-yn-1-yl)benzene With lithium diisopropyl amide In tetrahydrofuran; ethylbenzene; pentane at 10℃; for 1h; Stage #2: iodobenzene With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide In tetrahydrofuran; ethylbenzene; pentane at 20℃;
89%	Stage #1: (hex-1-yn-1-yl)benzene With lithium diisopropyl amide In tetrahydrofuran; ethylbenzene; pentane at -78 - 20℃; for 1h; Inert atmosphere; Stage #2: With zinc dibromide In tetrahydrofuran; ethylbenzene; pentane at 20℃; Inert atmosphere; Stage #3: iodobenzene With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; ethylbenzene; pentane at 20℃; Inert atmosphere; regioselective reaction;