Name: 18542-45-5|1-(2-Propynyloxy)naphthalene|95% GC
Brand: Ambeed
SKU: A899216
Price: 22.0 USD
Availability: InStock
Rating: 95 (25 reviews)

1
[ 18542-45-5 ]
[ 230-62-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	In 1,2-dichloro-ethane at 70℃; for 1h;
93%	With C₁₆H₂₃AuBClN₂O₂ In benzene-d6 at 20℃; for 6h;
80%	In various solvent(s) for 0.0416667h; Irradiation;

72%	With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In dichloromethane at 25℃; for 0.25h; regioselective reaction;
62%	With N,N-diethylaniline at 180℃; for 4.5h;
	In diethylene glycol for 0.133333h; Heating;
	With N,N-diethylaniline Reflux;

Reference： [1]Efe, Christina; Lykakis, Ioannis N.; Stratakis, Manolis [Chemical Communications, 2011, vol. 47, # 2, p. 803 - 805]
[2]Kong, Lingbing; Ganguly, Rakesh; Li, Yongxin; Kinjo, Rei [Chemical Science, 2015, vol. 6, # 5, p. 2893 - 2902]
[3]Moghaddam, F. Matloubi; Sharifi, A.; Saidi, M. R. [Journal of Chemical Research - Part S, 1996, # 7, p. 338 - 339]
[4]Location in patent: experimental part Lykakis, Ioannis N.; Efe, Christina; Gryparis, Charis; Stratakis, Manolis [European Journal of Organic Chemistry, 2011, # 12, p. 2334 - 2338]
[5]Ishii; Ishikawa; Takeda; Ueki; Suzuki [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 5, p. 1148 - 1153]
[6]Balasubramanian, T.; Balasubramanian, K. K. [Journal of the Chemical Society. Chemical communications, 1992, # 24, p. 1760 - 1761]
[7]Li, Xiufen; Wang, Chaoqiong; Song, Jianqiao; Yang, Zhihong; Zi, Guofu; Hou, Guohua [Journal of Organic Chemistry, 2019, vol. 84, # 13, p. 8638 - 8645]

2
[ 90-15-3 ]
[ 106-96-7 ]
[ 18542-45-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: α-naphthol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃;
95%	Stage #1: α-naphthol With potassium carbonate In acetone for 0.5h; Stage #2: propargyl bromide In acetone for 20h; Reflux;
95%	With potassium carbonate In 1,2-dimethoxyethane; toluene at 20℃; for 7h; Inert atmosphere;	2.14 Representative procedure for the synthesis of O-propargylphenol 5 (5a-5o) General procedure: To a stirred solution of 3-methoxyphenol 4a (1.0 g, 8.06 mmol) in dimethylformamide (27 mL) was added potassium carbonate (2.2 g, 16.12 mmol) (using NaH as base for 5e-5g and 5l-5m) followed by 80% propargyl bromide in toluene (0.91 mL, 12.09 mmol) and the resultant mixture was stirred for 7 h at rt. Then, the reaction mixture was diluted with ethylacetate (30 mL), washed with H2O (3*20 mL). The mixture was then dried over anhydrous MgSO4, filtered and concentrated to afford the crude mixture, which was purified by column chromatography to obtain the desired product. Brown oil (602 mg, 3.31 mmol, 95%); 1H NMR (300 MHz, CDCl3) δ 8.43-8.34 (m, 1H), 7.94-7.84 (m, 1H), 7.63-7.51 (m, 3H), 7.45 (t, J=8.1 Hz, 1H), 6.99 (d, J=7.6 Hz, 1H), 4.93 (d, J=2.3 Hz, 2H), 2.61 (t, J=2.3 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ 153.5, 134.7, 127.6, 126.7, 125.8, 125.7, 125.6, 122.2, 121.4, 105.7, 78.8, 75.8, 56.3; IR (KBr) ν 3293, 2122, 1580, 1401 cm-1; HRMS (APCI) calcd for C13H11O [M+H]+ 183.0810, found 183.0809.

95%	With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; for 7h; Inert atmosphere;
93%	With potassium carbonate In acetone at 50℃; for 12h;	General Procedure for the Synthesis of Propargyloxycoumarins (15d-g) and Naphthalenes (15h-i) General procedure: To a solution of coumarins 17d-g/naphthols 17h-i (100 mmol) in dry acetone (10 mL), anhydrous potassium carbonate (150 mmol), and propargyl bromide 18 (150 mmol) were added. The resultant mixture was stirred and refluxed at 50 °C for 12 hours, then the mixture was cooled and filtered, and the solvent was removed under reduced pressure. The residue was treated with 15 mL of water and extracted with ethyl acetate. The combined organic phase was washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuum. The crude product thus obtained was purified by crystallization from ethyl acetate/hexane mixture to give propargyloxycoumarins 15d-g and propargyloxynaphthalenes 15h-i in 81%-95%yield.
91%	With potassium carbonate In acetone; toluene at 20℃; for 12h;
90%	Stage #1: α-naphthol With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
90%	With potassium carbonate In acetone for 5h; Inert atmosphere; Reflux;
87%	With potassium carbonate In acetone for 18h; Inert atmosphere; Reflux;
86.8%	With potassium carbonate In acetone for 4h; Reflux;	5 5.5.5. 1-Prop-2-ynyloxy-naphthalene (5d) General procedure: The aromatic phenol (3 mmol) and 3-bromo-prop-1-yne(0.25 ml, 3.2 mmol) was dissolved in acetone (15 mL) and addedpotassium carbonate (1.0 g, 7.3 mmol), then the mixture washeated to reflux for 4 h. Then the reaction mixture was cooled toroom temperature followed by filtration and evaporated in vacuoto get the desired product compound 1d-17d. Yield 86.8%; colorless oil; 1H NMR (300 MHz, CDCl3): d = 8.29(m, 1H, ArH), 7.82 (m, 1H, ArH), 7.55-7.48 (m, 3H, ArH), 7.40 (t,J = 8.0 Hz, 1H, ArH), 4.91 (d, J = 2.5 Hz, 2H, OCH2), 2.57 (q,J = 2.5 Hz, 1H, C„CH).
80.4%	With potassium carbonate In acetone for 4h; Heating;
79%	With potassium carbonate In acetone; toluene Reflux;	2 Synthesis of 8-propargyloxynaphthalene A mixture of 1-naphthol 5 (2.4 g, 0.015 mol), K2CO3 (6.2 g, 0.045 mol) and propargyl bromide (80%, w/w solution in toluene, 3.6 mL, 0.045 mol) in 40 mL of acetone was refluxed overnight. Insoluble precipitates were removed by filtration, and the filtrate was evaporated in vacuo. The residue was dissolved in CH2Cl2 (100 mL), and the organic layer was extracted with 1 M HCl solution (2* 50 mL) and brine. The yellow solution was dried under reduced pressure and further purified by flash column chromatography using PE/CH2Cl2 (10:1, v:v) as eluent to give the product as a colorless oil with a yield of 79% (Rf = 0.4). 1H NMR (400 MHz, CDCl3, TMS, ppm): δ = 2.55 (t, J = 2.4 Hz, 1H; H of CH≡C-), 4.91 (d, J = 2.4 Hz, 2H; H of CH≡C-CH2-), 6.95 (d, J = 7.6, 1H; H of naphthalene), 7.39 (t, J = 8.0 Hz, 1H; H of naphthalene), 7.45-7.53 (m, 3H; H of naphthalene), 7.81 (dd, J = 6.2, 3.2 Hz, 1H; H of naphthalene), 8.32-8.24 (m, 1H; H of naphthalene). Anal. Calcd. for C13H10O: C, 85.69%; H, 5.53%. Found: C, 85.40%; H, 5.73%. EI-MS: 182 [M+H]+.
75%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
75%	In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
71%	With potassium carbonate In acetone at 80℃; for 15h;
63.6%	With sodium hydroxide; magnesium sulfate In water	1 EXAMPLE 1 EXAMPLE 1 Into a reaction flask fitted with a stirrer, a thermometer, a nitrogen gas inlet tube and a reflux condenser, was placed 21.259 parts of 1-naphthol, 53.086 parts of deionized water, 6.675 parts of NaOH and 0.120 part of tetrabutylammoniumbromide and to this mixture, 18.859 parts of propargyl bromide was added dropwise and reacted at 80° C. for 6 hours. After completion of the reaction, the content was treated with a mixture of ether and deionized water and the ether layer was separated, added with magnesium sulfate and kept stand overnight. After filtering off magnesium sulfate, the ether solvent was removed by an evaporator and the residue was subjected to a column chromatography (silica gel 200 mesh) to obtain a purified 1propargyloxynaphthalene. Yield 63.6%
	With potassium carbonate; potassium iodide In acetone
	In acetone; toluene at 20℃;
	With potassium carbonate In N,N-dimethyl-formamide
	With potassium carbonate In acetone for 24h; Reflux;
	With caesium carbonate In N,N-dimethyl-formamide at 20℃;
	With potassium carbonate In acetone for 20h; Reflux; Inert atmosphere;
	Stage #1: α-naphthol With caesium carbonate In N,N-dimethyl-formamide for 0.333333h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃;
	With ammonia for 12h; Reflux;
	With potassium carbonate In acetone Reflux;
	Stage #1: α-naphthol With potassium carbonate In acetone for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: propargyl bromide In acetone at 20℃; for 5h; Inert atmosphere; Schlenk technique;
	With potassium carbonate In acetone at 60℃; for 12h;
	Alkaline conditions;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
	With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	General procedure for the synthesis of alkynes (2a-c) General procedure: A round bottom flask with stirbar was charged with natural precursor (1.0 mmol) and anhydrous DMF (10 ml) and thereaction flask was cooled to 0°C. To this solution, potassium carbonate (1.0 mmol) wasadded, followed by slow addition of propargyl bromide (1.2 mmol). The reaction mixturewas allowed to warm to room temperature and stirred overnight under argon. After completionof the reaction as confirmed by TLC, it was concentrated and water was added tothe residue. The compound was extracted with ethyl acetate, dried over anhydrous sodiumsulphate and concentrated under vacuo. The crude product was purified by column chromatographywith petroleum ether: ethyl acetate (8:2) to give the desired alkynes (2a-c) ingood to excellent yields. The synthesis of compound 2a [8-(Prop-2-ynyloxy)quinoline] hasbeen previously reported in our lab [20].
	Stage #1: α-naphthol With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 20℃; Inert atmosphere;
	With potassium carbonate In N,N-dimethyl-formamide at 35℃; for 8h;	General procedure for the synthesis of terminal alkynes 3, 9 and 12 General procedure: The terminal alkynes 3, 9 and 12 were synthesized49 by reacting α-naphthol (1)/β-naphthol(8)/hydroquinone (11, 1.0 mmol) with propargyl bromide (2, 1.5/1.5/2.5 mole ratio, respectively)in the presence of potassium carbonate (3.0/3.0/5.0 mole ratio, respectively) in drydimethylformamide under continuous stirring for 5-8 h at 35-45 °C (Schemes 1-3). Aftercompletion of reaction, 2 M HCl solution was added into the reaction mixture, the contentstirred for 5-10 min and then the product was extracted with ethyl acetate (3×50 mL). Theorganic layer was washed with saturated brine solution, dried using anhydrous sodium sulfate,filtered and evaporated to obtain the desired ether-linked terminal alkynes.
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;
	With potassium carbonate In acetone for 10h; Reflux;	4.3 General procedure for the preparation of propargyl ethers 5a-p General procedure: Propargyl bromide (1.2mmol) was added to a mixture of phenolic compounds 4a-p (1.0mmol) and K2CO3 (1.2mmol) in acetone (5mL) and the mixture was stirred under reflux for 10h. After completion of the reaction confirmed by TLC, the solid salts were separated by filtration and the filtrate was concentrated under reduced pressure to give corresponding pure propargyl ethers 5a-p.
	Stage #1: α-naphthol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
	With potassium carbonate In acetone Reflux;
	Stage #1: α-naphthol With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;
	Stage #1: α-naphthol With potassium carbonate In acetone at 70℃; for 0.5h; Stage #2: propargyl bromide In acetone at 70℃; for 8h;

Reference： [1]Zhang, Chenyun; Zhen, Long; Yao, Zhi; Jiang, Liqin [Organic Letters, 2019, vol. 21, # 4, p. 955 - 959]
[2]Location in patent: experimental part Yuan, Jin-Wei; Qu, Ling-Bo; Chen, Xiao-Lan; Qu, Zhi-Bo; Liu, Xiang-Qian; Ke, Dian-Dian [Journal of the Chinese Chemical Society, 2011, vol. 58, # 1, p. 24 - 30]
[3]Chen, Ying-Yu; Chen, Kuan-Lin; Tyan, Yu-Chang; Liang, Chien-Fu; Lin, Po-Chiao [Tetrahedron, 2015, vol. 71, # 36, p. 6210 - 6218]
[4]Chou, Chih-Hung; Chen, Ying-Yu; Rajagopal, Basker; Tu, Hsiu-Chung; Chen, Kuan-Lin; Wang, Sheng-Fu; Liang, Chien-Fu; Tyan, Yu-Chang; Lin, Po-Chiao [Chemistry - An Asian Journal, 2016, vol. 11, # 5, p. 757 - 765]
[5]Arya, Anu; Mathur, Divya; Tyagi, Abhilash; Kumar, Rajesh; Kumar, Vinod; Olsen, Carl E.; Saxena, Rajendra K.; Prasad, Ashok K. [Nucleosides, nucleotides and nucleic acids, 2013, vol. 32, # 12, p. 646 - 659]
[6]Location in patent: experimental part Ke, Chenfeng; Yang, Cheng; Yang, Zixin; Wu, Weijia; Mori, Tadashi; Inoue, Yoshihisa; Liu, Yu [Heterocycles, 2008, vol. 76, # 1, p. 155 - 160]
[7]Wang, Yanzhao; Ji, Kegong; Lan, Sylvester; Zhang, Liming [Angewandte Chemie - International Edition, 2012, vol. 51, # 8, p. 1915 - 1918]
[8]Chatterjee, Soumit; Dey, Swapan; Hira, Sumit K.; Mondal, Surajit; Nayek, Hari Pada; Patra, Niladri [Photochemical and Photobiological Sciences, 2020, vol. 19, # 9, p. 1211 - 1221]
[9]Location in patent: experimental part Schuh, Esther; Valiahdi, Seied M.; Jakupec, Michael A.; Keppler, Bernhard K.; Chiba, Peter; Mohr, Fabian [Dalton Transactions, 2009, # 48, p. 10841 - 10845]
[10]Wu, Yuxiang; Pan, Miaobo; Dai, Yuxuan; Liu, Baomin; Cui, Jian; Shi, Wei; Qiu, Qianqian; Huang, Wenlong; Qian, Hai [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 10, p. 2287 - 2297]
[11]Ishii; Ishikawa; Takeda; Ueki; Suzuki [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 5, p. 1148 - 1153]
[12]Li, Nan; Chen, Yong; Zhang, Ying-Ming; Wang, Li-Hua; Mao, Wen-Zhao; Liu, Yu [Thermochimica Acta, 2014, vol. 576, p. 18 - 26]
[13]Sirivolu, Venkata Ramana; Vernekar, Sanjeev Kumar V.; Ilina, Tatiana; Myshakina, Nataliya S.; Parniak, Michael A.; Wang, Zhengqiang [Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8765 - 8780]
[14]Vernekar, Sanjeev Kumar V.; Qiu, Li; Zacharias, Jeana; Geraghty, Robert J.; Wang, Zhengqiang [MedChemComm, 2014, vol. 5, # 5, p. 603 - 608]
[15]Batool, Tannaza; Rasool, Nasir; Gull, Yasmeen; Noreen, Mnaza; Nasim, Faiz-Ul-Hassan; Yaqoob, Asma; Zubair, Muhammad; Rana, Usman Ali; Ud-Din Khan, Salah; Zia-Ul-Haq; Jaafar, Hawa Z. E. [PLoS ONE, 2014, vol. 9, # 12]
[16]Current Patent Assignee: WUTHELAM HOLDINGS PTE LTD - US5340931, 1994, A
[17]Hunter,W.H. et al. [Journal of Medicinal Chemistry, 1964, vol. 7, p. 167 - 174]
[18]Punna, Sreenivas; Meunier, Stephane; Finn [Organic Letters, 2004, vol. 6, # 16, p. 2777 - 2779]
[19]Location in patent: body text Chaudhary, Preeti M.; Chavan, Sayalee R.; Shirazi, Fazal; Razdan, Meenakshi; Nimkar, Prachi; Maybhate, Shailaja P.; Likhite, Anjali P.; Gonnade, Rajesh; Hazara, Braja G.; Deshpande, Mukund V.; Deshpande, Sunita R. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 6, p. 2433 - 2440]
[20]Location in patent: body text Godoi, Benhur; Speranca, Adriane; Back, Davi F.; Brandao, Ricardo; Nogueira, Cristina W.; Zeni, Gilson [Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3469 - 3477]
[21]Efe, Christina; Lykakis, Ioannis N.; Stratakis, Manolis [Chemical Communications, 2011, vol. 47, # 2, p. 803 - 805]
[22]Zhang, Jian; Wu, Jingjing; Shen, Li; Jin, Guanyi; Cao, Song [Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 580 - 584]
[23]Lykakis, Ioannis N.; Efe, Christina; Gryparis, Charis; Stratakis, Manolis [European Journal of Organic Chemistry, 2011, # 12, p. 2334 - 2338]
[24]Ramchander; Rameshwar; Reddy, T Sheshashena; Raju, Gajula; Reddy, A Ram [Journal of Chemical Sciences, 2014, vol. 126, # 4, p. 1063 - 1074]
[25]Omirzak; Erkasov; Sukhov; Ganenko [Russian Chemical Bulletin, 2013, vol. 62, # 11, p. 2442 - 2444][Izv. Akad. Nauk, Ser. Khim., 2013, # 11, p. 2442 - 2444,3]
[26]Tang, Xiang-Ying; Zhang, Yong-Sheng; He, Lv; Wei, Yin; Shi, Min [Chemical Communications, 2014, vol. 51, # 1, p. 133 - 136]
[27]Arya, Anu; Kumar, Vinod; Mathur, Divya; Singh, Sukhdev; Brahma, Raju; Singh, Rajpal; Singh, Seema; Sharma; Parmar, Virinder S.; Prasad, Ashok K. [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 1 - 14] Mathur; Rana; Olsen; Parmar; Prasad [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 3, p. 701 - 710]
[28]Negi, Beena; Kumar, Deepak; Kumbukgolla, Widuranga; Jayaweera, Sampath; Ponnan, Prija; Singh, Ramandeep; Agarwal, Sakshi; Rawat, Diwan S. [European Journal of Medicinal Chemistry, 2016, vol. 115, p. e426 - e437]
[29]Khaligh, Pooneh; Salehi, Peyman; Bararjanian, Morteza; Aliahmadi, Atousa; Khavasi, Hamid Reza; Nejad-Ebrahimi, Samad [Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 11, p. 1589 - 1596]
[30]Irfan, Mohammad; Alam, Shadab; Manzoor, Nikhat; Abid, Mohammad [PLoS ONE, 2017, vol. 12, # 4]
[31]Bernar, Ivan; Fiser, Béla; Blanco-Ania, Daniel; Gómez-Bengoa, Enrique; Rutjes, Floris P. J. T. [Organic Letters, 2017, vol. 19, # 16, p. 4211 - 4214]
[32]Kaushik, Chander Prakash; Kumar, Krishan; Kumar, Devinder; Mor, Satbir; Kumar, Ashwani; Jindal, Deepak Kumar [Journal of the Serbian Chemical Society, 2017, vol. 82, # 9, p. 995 - 1007]
[33]Kummari, Bhaskar; Polkam, Naveen; Ramesh, Perla; Anantaraju, Hasithashilpa; Yogeeswari, Perumal; Anireddy, Jaya Shree; Guggilapu, Sravanthi Devi; Babu, Bathini Nagendra [RSC Advances, 2017, vol. 7, # 38, p. 23680 - 23686]
[34]Ashooriha, Morteza; Khoshneviszadeh, Mehdi; Khoshneviszadeh, Mahsima; Moradi, Seyed Ershad; Rafiei, Alireza; Kardan, Mostafa; Emami, Saeed [Bioorganic Chemistry, 2019, vol. 82, p. 414 - 422]
[35]Fang, Jun-Dan; Yan, Xiao-Biao; Zhou, Li; Wang, Yu-Zhao; Liu, Xue-Yuan [Advanced Synthesis and Catalysis, 2019, vol. 361, # 9, p. 1985 - 1990]
[36]Li, Xiufen; Wang, Chaoqiong; Song, Jianqiao; Yang, Zhihong; Zi, Guofu; Hou, Guohua [Journal of Organic Chemistry, 2019, vol. 84, # 13, p. 8638 - 8645]
[37]Fang, Jun-Dan; Yan, Xiao-Biao; Lin, Wu-Jie; Zhao, Yi-Chuan; Liu, Xue-Yuan [Organic Letters, 2019, vol. 21, # 18, p. 7635 - 7638]
[38]Kaushik, Chander Prakash; Luxmi, Raj [Journal of Heterocyclic Chemistry, 2020, vol. 57, # 6, p. 2400 - 2409]
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3
[ 75-77-4 ]
[ 18542-45-5 ]
1-naphthyl trimethylsilylpropargyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With n-butyllithium In diethyl ether; hexane for 1.5h; Ambient temperature;

Reference： [1]Saidi, Mohammad Reza; Zadmard, Reza; Saberi, Tahereh [Heterocycles, 1996, vol. 43, # 4, p. 751 - 754]

4
[ 18542-45-5 ]
[ 25826-63-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium methylate In various solvent(s) for 0.0416667h; Irradiation;
58%	With Echavarren's catalyst In dichloromethane at 18℃; for 3h; Inert atmosphere;

Reference： [1]Moghaddam, F. Matloubi; Sharifi, A.; Saidi, M. R. [Journal of Chemical Research - Part S, 1996, # 7, p. 338 - 339]
[2]Menon, Rajeev S.; Findlay, Alison D.; Bissember, Alex C.; Banwell, Martin G. [Journal of Organic Chemistry, 2009, vol. 74, # 22, p. 8901 - 8903]

5
[ 18542-45-5 ]
1-[(propa-1,2-dien-1-yl)oxy]naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide for 0.0333333h; microwave irradiation;
	With potassium <i>tert</i>-butylate In water; <i>tert</i>-butyl alcohol	1 EXAMPLE 1 Into a similar reaction vessel as used in the abovementioned reaction, were placed 1.532 parts of t-BuOK and 6.816 parts of t-BuOH and to this, a mixture of 10.000 parts of 1-propargyloxynaphthalene and 23.333 parts of t-BuOH was dropwise added. The content was reacted at 50° C. for 60 minutes and then deionized water was added to stop the reaction. t-BuOH layer and water layer were removed off by using an evaporator, and the residue was added with an aqueous NaOH solution, extracted with an ether and the ether layer was separated. The ether solvent was removed off and the residue was subjected to a column chromatography (silica gel 200 mesh) to obtain a purified 1-allenyloxy naphthalene as a colorless oily product.
	With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Moghaddam, Firouz Matloubi; Emami, Rahdar [Synthetic Communications, 1997, vol. 27, # 23, p. 4073 - 4077]
[2]Current Patent Assignee: WUTHELAM HOLDINGS PTE LTD - US5340931, 1994, A
[3]Bernar, Ivan; Fiser, Béla; Blanco-Ania, Daniel; Gómez-Bengoa, Enrique; Rutjes, Floris P. J. T. [Organic Letters, 2017, vol. 19, # 16, p. 4211 - 4214]

6
[ 123-75-1 ]
[ 50-00-0 ]
[ 18542-45-5 ]
1-[4-(naphthalen-1-yloxy)-but-2-ynyl]-pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With aluminum oxide; copper(l) chloride In water for 0.0166667h; microwave irradiation;

Reference： [1]Sharifi, Ali; Farhangian, Hossein; Mohsenzadeh, Farshid; Naimi-Jamal [Monatshefte fur Chemie, 2002, vol. 133, # 2, p. 199 - 204]

7
[ 110-89-4 ]
[ 50-00-0 ]
[ 18542-45-5 ]
1-[4-(naphthalen-1-yloxy)-but-2-ynyl]-piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With aluminum oxide; copper(l) chloride In water for 0.0166667h; microwave irradiation;

Reference： [1]Sharifi, Ali; Farhangian, Hossein; Mohsenzadeh, Farshid; Naimi-Jamal [Monatshefte fur Chemie, 2002, vol. 133, # 2, p. 199 - 204]

8
[ 110-91-8 ]
[ 50-00-0 ]
[ 18542-45-5 ]
4-[4-(naphthalen-1-yloxy)-but-2-ynyl]-morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With aluminum oxide; copper(l) chloride In water for 0.0166667h; microwave irradiation;

Reference： [1]Sharifi, Ali; Farhangian, Hossein; Mohsenzadeh, Farshid; Naimi-Jamal [Monatshefte fur Chemie, 2002, vol. 133, # 2, p. 199 - 204]

9
[ 50-00-0 ]
[ 18542-45-5 ]
[ 109-89-7 ]
diethyl-[4-(naphthalen-1-yloxy)-but-2-ynyl]-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With aluminum oxide; copper(l) chloride In water for 0.0166667h; microwave irradiation;

Reference： [1]Sharifi, Ali; Farhangian, Hossein; Mohsenzadeh, Farshid; Naimi-Jamal [Monatshefte fur Chemie, 2002, vol. 133, # 2, p. 199 - 204]

10
[ 18542-45-5 ]
1,1'-[2,4-hexadiyne-1,6-diylbis(oxy]bisnaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With morpholine; aluminum oxide; potassium fluoride; copper diacetate at 20℃; for 3h;
40%	With morpholine; aluminum oxide for 0.116667h; microwave irradiation;
83 %Chromat.	With morpholine In neat (no solvent) at 60℃; for 9h; Green chemistry;	2.7. General procedure for aerobic oxidative homocouplingreaction of terminal alkyne General procedure: Terminal alkyne (1 mmol), morpholine (1.2 mmol), and catalyst MNPNNN-Pincer/Cu were loaded in a 25 mL round bottom flask. The reactants were vigorously stirred at room temperature (or 60°C) for a defined time (the amount of catalyst loading and temperature were selected according to Table 3). Completion of the reaction was monitored by TLC until the initial alkyne consumed and no further product (comparing with the related known product by TLC) was formed. After completion of the reaction, methanol was added and the catalyst was magnetically separated, washed with methanol (3 × 10 mL) and dried for another run. The productmixtures were analyzed by gas chromatography (GC). The isolated yields of products were determined after purification of product using column chromatography (hexane/ethyl acetate as eluent).

Reference： [1]Sharifi, Ali; Mirzaei, Mojtaba; Reza Naimi-Jamal [Monatshefte fur Chemie, 2006, vol. 137, # 2, p. 213 - 217]
[2]Sharifi, Ali; Mirzaei, Mojtaba; Naimi-Jamal, Mohammad Reza [Journal of Chemical Research - Part S, 2002, # 12, p. 628 - 630]
[3]Zohreh, Nasrin; Jahani, Mahboobeh [Journal of Molecular Catalysis A: Chemical, 2017, vol. 426, p. 117 - 129]

11
[ 18542-45-5 ]
[ 108-94-1 ]
1-[3-(naphthalen-1-yloxy)-prop-1-ynyl]-cyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium fluoride on basic alumina at 60℃; for 20h;

Reference： [1]Sharifi, Ali; Mirzaei, Mojtaba; Naimi-Jamal, M. Reza [Synthetic Communications, 2005, vol. 35, # 8, p. 1039 - 1044]

12
[ 18542-45-5 ]
[ 106-95-6 ]
1-(2-methylene-pent-4-enyloxy)-naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With zinc at 27℃; for 2.5h;

Reference： [1]Yadav; Reddy; Reddy, P. Murali Krishna; Gupta, Manoj K. [Tetrahedron Letters, 2005, vol. 46, # 48, p. 8411 - 8413]

13
[ 158072-92-5 ]
[ 18542-45-5 ]
[ 1079252-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl 3-bromo-1-(4-methoxybenzyl)-1H-indole-2-carboxylate With caesium carbonate; XPhos In acetonitrile at 20℃; for 0.416667h; Stage #2: 1-(propargyloxy)naphthalene In acetonitrile at 80℃; for 3h;	102.A EXAMPLE 102A ethyl 1 -(4-methoxybenzyl)-3 -(3 -(naphthalen- 1 -yloxy)prop- 1 -ynyl)- 1 H-indole-2-carboxylate To a solution of EXAMPLE 101B (3.89 g) in acetonitrile (20 ml) was addedPd(PhCN)2Cl2 (38 mg), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (143 mg), and Cs2CC>3 (3.91 g). The mixture was purged with argon and stirred at room temperature for 25 minutes. After this time, l-(prop-2-ynyloxy)naphthalene (2.2 g) was added to the mixture which was purged with argon again. The mixture was then stirred at 8O0C for 3 hours. The mixture was diluted with ethyl acetate (300 ml) and washed with water, brine and dried over Na2SO4. After filtration, the solvent was concentrated and the residue was loaded on a silica gel column and eluted with 5% ethyl acetate in hexane to give EXAMPLE 102A.

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2008/130970, 2008, A1 Location in patent: Page/Page column 101

14
[ 18542-45-5 ]
silver nitrate [ No CAS ]
[ 1048033-12-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With Et₃N In acetonitrile under N2; AgNO3 dissolved in MeCN; ligand and Et3N added with stirring; stirred overnight in darkness; filtered; ppt. washed with MeCN and deionized H2O; stored at -10°C;

Reference： [1]Zang, Shuang-Quan; Mak, Thomas C. W. [Inorganic Chemistry, 2008, vol. 47, # 16, p. 7094 - 7105]

15
[ 18542-45-5 ]
[ 15083-05-3 ]
[ 1152593-87-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(ll) sulfate pentahydrate; sodium ascorbate In water; <i>tert</i>-butyl alcohol at 28℃;

Reference： [1]Location in patent: experimental part Chaudhary, Preeti M.; Chavan, Sayalee R.; Shirazi, Fazal; Razdan, Meenakshi; Nimkar, Prachi; Maybhate, Shailaja P.; Likhite, Anjali P.; Gonnade, Rajesh; Hazara, Braja G.; Deshpande, Mukund V.; Deshpande, Sunita R. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 6, p. 2433 - 2440]

16
[ 34837-55-3 ]
[ 18542-45-5 ]
[ 1147710-94-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere;
60%	Stage #1: 1-(propargyloxy)naphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: Phenylselenyl bromide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;

Reference： [1]Eom, Dahan; Park, Sangjune; Park, Youngchul; Lee, Kooyeon; Hong, Gilbert; Lee, Phil Ho [European Journal of Organic Chemistry, 2013, # 13, p. 2672 - 2682]
[2]Godoi, Benhur; Speranca, Adriane; Back, Davi F.; Brandao, Ricardo; Nogueira, Cristina W.; Zeni, Gilson [Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3469 - 3477]

17
[ 14243-64-2 ]
[ 18542-45-5 ]
[ 1206552-75-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With KOH In ethanol; methanol byproducts: KCl; (N2, Schlenk technique); addn. of methanolic soln. of KOH to soln. of acetylene deriv. in 1:1 methanol/ethanol, stirring for 5 min, addn. of gold compd., stirring at reflux for 1 h; cooling, concg., addn. of hexane, isolation of ppt., dissolving in CH2Cl2, filtration through celite, addn. of hexane, isolation of ppt., elem. anal.;

Reference： [1]Schuh, Esther; Valiahdi, Seied M.; Jakupec, Michael A.; Keppler, Bernhard K.; Chiba, Peter; Mohr, Fabian [Dalton Transactions, 2009, # 48, p. 10841 - 10845]

18
6-azido-6-deoxy-β-CD [ No CAS ]
[ 18542-45-5 ]
C₅₅H₇₉N₃O₃₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 60℃; for 48h;

Reference： [1]Location in patent: experimental part Ke, Chenfeng; Yang, Cheng; Yang, Zixin; Wu, Weijia; Mori, Tadashi; Inoue, Yoshihisa; Liu, Yu [Heterocycles, 2008, vol. 76, # 1, p. 155 - 160]

19
[ 1262850-20-3 ]
[ 18542-45-5 ]
[ 1292210-31-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 2,2-difluoro-2-(phenylthio)ethan-1-ol With sodium azide; tetra-(n-butyl)ammonium iodide; triethylamine; N-tosylimidazole In N,N-dimethyl-formamide at 100℃; for 10h; Stage #2: 1-(propargyloxy)naphthalene With copper(l) iodide In N,N-dimethyl-formamide at 20℃;

Reference： [1]Location in patent: experimental part Zhang, Jian; Wu, Jingjing; Shen, Li; Jin, Guanyi; Cao, Song [Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 580 - 584]

20
[ 18542-45-5 ]
[ 98-88-4 ]
[ 1334791-80-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With zinc(II) oxide at 20℃; for 0.166667h; optical yield given as %de; diastereoselective reaction;

Reference： [1]Location in patent: experimental part Hosseini-Sarvari, Mona; Mardaneh, Zahra [Bulletin of the Chemical Society of Japan, 2011, vol. 84, # 7, p. 778 - 782]

21
[ 18542-45-5 ]
[ 30516-87-1 ]
[ 1310031-52-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 1-(propargyloxy)naphthalene; 3'-azido-2',3'-deoxythymidine In water; <i>tert</i>-butyl alcohol at 20℃; for 0.166667h; Stage #2: With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃;
93%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 12h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yuan, Jin-Wei; Qu, Ling-Bo; Chen, Xiao-Lan; Qu, Zhi-Bo; Liu, Xiang-Qian; Ke, Dian-Dian [Journal of the Chinese Chemical Society, 2011, vol. 58, # 1, p. 24 - 30]
[2]Sirivolu, Venkata Ramana; Vernekar, Sanjeev Kumar V.; Ilina, Tatiana; Myshakina, Nataliya S.; Parniak, Michael A.; Wang, Zhengqiang [Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8765 - 8780]

22
[ 615-43-0 ]
[ 18542-45-5 ]
[ 1346019-30-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;

Reference： [1]Wang, Honggen; Zhao, Jiaji; Zhang, Jiancun; Zhu, Qiang [Advanced Synthesis and Catalysis, 2011, vol. 353, # 14-15, p. 2653 - 2658]

23
[ 18542-45-5 ]
[ 78-84-2 ]
[ 1356019-35-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	With zinc(II) oxide at 120℃; for 11h; Neat (no solvent);

Reference： [1]Location in patent: experimental part Hosseini-Sarvari, Mona; Mardaneh, Zahra [Bulletin of the Korean Chemical Society, 2011, vol. 32, # 12, p. 4297 - 4303]

24
[ 18542-45-5 ]
[ 90-15-3 ]

Yield	Reaction Conditions	Operation in experiment
69%	With palladium on activated charcoal; ethanolamine In water at 80℃; Inert atmosphere;

Reference： [1]Rambabu; Bhavani; Swamy, Nalivela Kumara; Basaveswara Rao; Pal, Manojit [Tetrahedron Letters, 2013, vol. 54, # 9, p. 1169 - 1173]

25
[ 18542-45-5 ]
[ 30516-87-1 ]
[ 1476031-99-8 ]

Yield	Reaction Conditions	Operation in experiment
27%	With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In tetrahydrofuran at 60℃; Inert atmosphere;

Reference： [1]Sirivolu, Venkata Ramana; Vernekar, Sanjeev Kumar V.; Ilina, Tatiana; Myshakina, Nataliya S.; Parniak, Michael A.; Wang, Zhengqiang [Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8765 - 8780]

26
[ 18542-45-5 ]
[ 98169-85-8 ]
[ 1075201-80-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 1-(propargyloxy)naphthalene; mono(6-azido-6-deoxy)β-cyclodextrin With copper(ll) sulfate pentahydrate In tetrahydrofuran; water at 50℃; for 0.166667h; Stage #2: With sodium L-ascorbate In tetrahydrofuran; water at 50℃; Inert atmosphere;	3 Synthesis of mono-6-deoxy-6-{4-(8-oxymethylnaphthol)[1,2,3]triazolyl}-β-CD (3) 8-Propargyloxynaphthalene 6 (328 mg, 1.80 mmol) in 15 mL of THF was added to a solution of CuSO4·5H2O (600 mg, 2.40 mmol) and mono-6-deoxyl-6-azido-β-CD 8 (1.39 g, 1.20 mmol) in 35 mL of water. The mixture was kept at 50 °C for 10 min, and then sodium ascorbate (1.42 g, 7.20 mmol) was added. The color of the mixture turned orange immediately. Then, the mixture was heated at 50 °C under an atmosphere of N2 overnight. After cooled to room temperature, insoluble precipitates were removed by filtration, and the filtrate was evaporated in vacuo. The residue was dissolved in a small amount of water, and washed with 300 mL of acetone for at least three times. After separation by column chromatography (silica gel) using n-PrOH:H2O:NH3·H2O (6:3:1, v:v:v) as eluent, 3 was obtained as a white solid with a yield of 70% (Rf = 0.4). 1H NMR (400 MHz, DMSO-d6, ppm) δ = 3.65 (dd, J = 40.2, 19.4 Hz, 24H; C2-6 H of β-CD), 4.54 (dd, J = 41.9, 20.9 Hz, 6H; O-6 H of β-CD), 4.96-4.78 (m, 7H; C-1 H of β-CD), 5.30 (s, 2H; H of -CH2-), 5.97-5.62 (m, 14H; O-2, 3 H of β-CD), 7.19 (d, J = 7.7 Hz, 1H; H of naphthalene), 7.55-7.41 (m, 4H; H of naphthalene), 7.87 (d, J = 8.2 Hz, 1H; H of naphthalene), 8.11 (d, J = 8.0 Hz, 1H; H of naphthalene), 8.28 (s, 1H; H of triazole). Anal. Calcd. for C55H79N3O35·2H2O: C, 47.93%; H, 6.07%; N, 3.05%. Found: C, 47.90%; H, 6.27%; N, 3.12%. ESI-MS: 1364 [M+H]+.

Reference： [1]Li, Nan; Chen, Yong; Zhang, Ying-Ming; Wang, Li-Hua; Mao, Wen-Zhao; Liu, Yu [Thermochimica Acta, 2014, vol. 576, p. 18 - 26]

27
[ 18542-45-5 ]
[ 215176-58-2 ]
[ 1519007-61-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) iodide In tetrahydrofuran; ethanol; water at 60℃; for 15h;	General Procedure for the Synthesis of 3'-Substituted Triazolylnucleosides (16a-i) General procedure: To a solution of 3'-azido-3'-deoxy-5-methyluridine (14, 3.60 mmol) and alkynes 15a-i (4.32 mmol) in EtOH:H2O:THF (3 mL, 1:1:1), copper(I) iodide (0.54 mmol) was added. Thereafter, the reaction mixture was stirred at 60 °C and the reaction was monitored by TLC. On completion of the reaction the solvent was evaporated under reduced pressure and the crude product thus obtained was purified by silica gel column chromatography usingmethanol/chloroform as eluting solvent to afford the desired products 16a-i.

Reference： [1]Arya, Anu; Mathur, Divya; Tyagi, Abhilash; Kumar, Rajesh; Kumar, Vinod; Olsen, Carl E.; Saxena, Rajendra K.; Prasad, Ashok K. [Nucleosides, nucleotides and nucleic acids, 2013, vol. 32, # 12, p. 646 - 659]

28
[ 18542-45-5 ]
[ 1456736-75-6 ]
[ 1456736-79-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With Vitamin C; copper(II) sulfate pentahydrate In water; <i>tert</i>-butyl alcohol at 20℃; for 2h;
	With copper(ll) sulfate pentahydrate; (+)-sodium ascorbate In water; <i>tert</i>-butyl alcohol at 20℃;

Reference： [1]Pingaew, Ratchanok; Prachayasittikul, Supaluk; Ruchirawat, Somsak; Prachayasittikul, Virapong [Medicinal Chemistry Research, 2014, vol. 23, # 4, p. 1768 - 1780]
[2]Pingaew, Ratchanok; Prachayasittikul, Veda; Mandi, Prasit; Nantasenamat, Chanin; Prachayasittikul, Supaluk; Ruchirawat, Somsak; Prachayasittikul, Virapong [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3472 - 3480]

29
[ 1445-73-4 ]
[ 18542-45-5 ]
1-methyl-4-[3-(1-naphthyloxy)prop-1-ynyl]piperidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 1-(propargyloxy)naphthalene With potassium hydroxide In diethyl ether at 21℃; for 0.5h; Stage #2: 1-Methyl-4-piperidone In diethyl ether at 21℃;

Reference： [1]Omirzak; Erkasov; Sukhov; Ganenko [Russian Chemical Bulletin, 2013, vol. 62, # 11, p. 2442 - 2444][Izv. Akad. Nauk, Ser. Khim., 2013, # 11, p. 2442 - 2444,3]

30
[ 23133-37-1 ]
[ 18542-45-5 ]
4-[3-(1-naphthyloxy)prop-1-ynyl]-1-propylpiperidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 1-(propargyloxy)naphthalene With potassium hydroxide In diethyl ether at 21℃; for 0.5h; Stage #2: 1-propyl-4-piperidone In diethyl ether at 21℃;

Reference： [1]Omirzak; Erkasov; Sukhov; Ganenko [Russian Chemical Bulletin, 2013, vol. 62, # 11, p. 2442 - 2444][Izv. Akad. Nauk, Ser. Khim., 2013, # 11, p. 2442 - 2444,3]

31
[ 941-55-9 ]
[ 18542-45-5 ]
4-(naphthalen-1-yloxymethyl)-1-(toluene-4-sulfonyl)-1H-[1,2,3]triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(II) thiophene-2-carboxylate In toluene at 20℃; for 2h; Inert atmosphere;	14 Representative procedure for the synthesis of O-sulfonyltriazoles 1 (1a-1o) General procedure: The procedure for the preparation of compound 1a is representative for all O-sulfonyltriazoles 1. To a stirred solution of 1-methoxy-3-(prop-2-ynyloxy)benzene (5a) (1.0 g, 6.17 mmol) in toluene (31 mL) was added copper thiophene carboxylic acid (118 mg, 0.62 mmol) and tosyl azide (1.34 g, 6.79 mmol) and the resultant mixture was stirred for 2 h at rt. The reaction mixture was treated with cuprisorb resin (14.0 g) for 30 min, filtered through a Celite pad, washed with dichloromethane (20 mL) and evaporated to afford the crude compound, which was purified by silica gel column chromatography using 20% ethylacetate in hexane as a solvent system to afford the desired product. White solid (1.04 g, 2.74 mmol, 83%); mp 121-123 °C; 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 8.25-8.18 (m, 1H), 8.02 (d, J=8.5 Hz, 2H), 7.85-7.78 (m, 1H), 7.55-7.44 (m, 3H), 7.43-7.33 (m, 3H), 6.91 (d, J=7.5 Hz, 1H), 5.39 (s, 2H), 2.46 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 153.9, 147.7, 144.5, 134.8, 133.2, 130.7, 129.0, 127.8, 126.8, 125.9, 125.7, 122.6, 122.0, 121.5, 105.5, 62.2, 22.1; IR (KBr) ν 3427, 1926, 1595 cm-1; HRMS (MALDI) calcd for C20H18N3O3S [M+H]+ 380.1063, found 380.1064.
83%	With copper(I) thiophene-2-carboxylate In toluene at 20℃; for 2h; Inert atmosphere;
308 mg	Stage #1: 1-(propargyloxy)naphthalene With copper(I) thiophene-2-carboxylate In toluene at 20℃; for 0.05h; Inert atmosphere; Schlenk technique; Stage #2: 4-toluenesulfonyl azide In toluene at 20℃; for 4h; Inert atmosphere; Schlenk technique;

Reference： [1]Chen, Ying-Yu; Chen, Kuan-Lin; Tyan, Yu-Chang; Liang, Chien-Fu; Lin, Po-Chiao [Tetrahedron, 2015, vol. 71, # 36, p. 6210 - 6218]
[2]Chou, Chih-Hung; Chen, Ying-Yu; Rajagopal, Basker; Tu, Hsiu-Chung; Chen, Kuan-Lin; Wang, Sheng-Fu; Liang, Chien-Fu; Tyan, Yu-Chang; Lin, Po-Chiao [Chemistry - An Asian Journal, 2016, vol. 11, # 5, p. 757 - 765]
[3]Tang, Xiang-Ying; Zhang, Yong-Sheng; He, Lv; Wei, Yin; Shi, Min [Chemical Communications, 2014, vol. 51, # 1, p. 133 - 136]

32
[ 18542-45-5 ]
7-(3-azido-2-hydroxypropyloxy)-3-hexyl-4-methylcoumarin [ No CAS ]
3-Hexyl-7-[2-hydroxy-3-(4-(naphthalen-1-yloxymethyl)-1,2,3-triazol-1-yl)propyloxy]-4-methylcoumarin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; <i>tert</i>-butyl alcohol at 60℃;

Reference： [1]Arya, Anu; Kumar, Vinod; Mathur, Divya; Singh, Sukhdev; Brahma, Raju; Singh, Rajpal; Singh, Seema; Sharma; Parmar, Virinder S.; Prasad, Ashok K. [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 1 - 14]

33
[ 18542-45-5 ]
7-(3-azido-2-hydroxypropyloxy)-3-ethyl-4-methylcoumarin [ No CAS ]
3-ethyl-7-[2-hydroxy-3-(4-(naphthalen-1-yloxymethyl)-1,2,3-triazol-1-yl)propyloxy]-4-methylcoumarin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; <i>tert</i>-butyl alcohol at 60℃;

Reference： [1]Arya, Anu; Kumar, Vinod; Mathur, Divya; Singh, Sukhdev; Brahma, Raju; Singh, Rajpal; Singh, Seema; Sharma; Parmar, Virinder S.; Prasad, Ashok K. [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 1 - 14]

34
[ 18542-45-5 ]
[ 26929-65-7 ]
2′-deoxy-2′-(4-naphthalen-1-yloxymethyl-1,2,3-triazol-1-yl)uridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; <i>tert</i>-butyl alcohol at 20℃;

Reference： [1]Mathur; Rana; Olsen; Parmar; Prasad [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 3, p. 701 - 710]

35
[ 18542-45-5 ]
[ 97748-75-9 ]
2'-deoxy-2'-(4-naphthalen-1-yloxymethyl-1,2,3-triazol-1-yl)-5-methyluridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; <i>tert</i>-butyl alcohol at 20℃;

Reference： [1]Mathur; Rana; Olsen; Parmar; Prasad [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 3, p. 701 - 710]

36
[ 18542-45-5 ]
3-azido-5-chloro-2-hydroxybenzoic acid [ No CAS ]
5-chloro-2-hydroxy-3-[4-(naphthalen-1-yloxymethyl)-1H-1,2,3-triazol-1-yl]benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃;	The general procedure for the synthesis of 5-chloro-2-hydroxy-3-triazolylbenzoic acids (5) General procedure: In a 250-mL three-necked round-bottom flask was added20 mL of tert-butanol/water (V:V = 1:1) mixed solutioncontaining 3-azido-5-chloro-2-hydroxybenzoic acid(427 mg, 2 mmol) and terminal alkyne (2.2 mmol). To thissolution were then added sodium ascorbate (200 mg,1 mmol, 50 % equiv.) and CuSO45H2O (50 mg,0.2 mmol, 10 % equiv.). The reaction mixture was stirredfor about 8-12 h at room temperature. The precipitate wasfiltered, washed with water and then petroleum ether, anddried under vacuum to give gray solid.

Reference： [1]Chen, Jie; Liu, Cheng-Fu; Yang, Cheng-Wen; Zeng, Cheng-Chu; Liu, Wei; Hu, Li-Ming [Medicinal Chemistry Research, 2015, vol. 24, # 7, p. 2950 - 2959]

37
[ 936320-68-2 ]
[ 18542-45-5 ]
(E)-methyl 2-(2-((4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-3-methoxyacrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 28℃;	General procedure for the synthesis of 1,2,3-triazolesubstituted strobilurin derivatives, 10a-i To a stirred solution of (E)-methyl 2-(2-(azidomethyl)-phenyl)-3-methoxyacrylate 6 (1 mmol) and specific propargyl ethers of phenols 9a-i (1 mmol) in 10 mL of tertiary butanol/water (8:2), copper sulphate (24 mg, 5mol %) and sodium ascorbate (40 mg, 10 mol %) were added. Reaction mixture was stirred at 28°C for 3-6 h. On completion of the reaction (monitored by TLC), t-butanol was removed under reduced pressure and the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed subsequently with 3×35 mL of water, 35 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to get crude product. Finally, the crude product was purified by silica gel columnchromatography using ethyl acetate and petroleum ether as eluent to obtain pure 1,2,3-triazole derivatives of strobilurin 10a-i.

Reference： [1]Chaudhary, Preeti M.; Tupe, Santosh G.; Jorwekar, Shweta U.; Sant, Duhita G.; Deshpande, Sunita R.; Maybhate, Shailaja P.; Likhite, Anjali P.; Deshpande, Mukund V. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 7, p. 908 - 917]

38
[ 18542-45-5 ]
[ 60666-28-6 ]
1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 2h;	5.23 Typical procedure for the synthesis of metronidazole-triazole conjugates (4-38) General procedure: To a vigorously stirred solution of 1-(2-azido-ethyl)-2-methyl-5-nitro-1H-imidazole (3), (2.5 mmol) and appropriate alkyne (2.5 mmol) in tert-butyl alcohol was added a solution of CuSO4.5H2O (0.51 mmol) and sodium ascorbate (1.02 mmol) in distilled water (Scheme 1). The amount of tert-butyl alcohol and distilled water was kept 1:1 (v/v). The deep yellow mixture was stirred vigorously at room temperature and progress of reaction was monitored by thin layer chromatography. After 2 h, reaction was completed and crude reaction mixture was extracted with CHCl3 (3 x 10 mL) and dried over anhydrous Na2SO4. Excess of solvent was removed under vaccum. The crude mixture was purified over SiO2 column using ethyl acetate/hexane as an eluent.

Reference： [1]Negi, Beena; Kumar, Deepak; Kumbukgolla, Widuranga; Jayaweera, Sampath; Ponnan, Prija; Singh, Ramandeep; Agarwal, Sakshi; Rawat, Diwan S. [European Journal of Medicinal Chemistry, 2016, vol. 115, p. e426 - e437]

39
[ 18542-45-5 ]
[ 1610805-19-0 ]
6,7-dimethoxy-2-(4-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)phenethyl)-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.5%	With Cu⁽²⁺⁾*CuO₄^(2-); sodium L-ascorbate In methanol at 20℃;	5 5.6.5. 6,7-Dimethoxy-2-(4-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)phenethyl)-1,2,3,4-tetrahydroisoquinoline (5) General procedure: To the solution of 1d-12d (1 mmol) and e(1 mmol) in 75%methanol (40 mL), ascorbate sodium (30 mg) and CuSO4 (10 mg)were added, respectively. The reaction solution was stirred at roomtemperature for 24-48 h. Then, the mixture was filtered to give thedesire product with high purity.. Yield 38.5%; pale yellow powder; mp: 130-132 C; 1H NMR(300 MHz, DMSO-d6): d = 9.02 (s, 1H, -CHC-), 8.20 (d, J = 7.9 Hz,1H, ArH), 7.89-7.84 (m, 3H, ArH), 7.54-7.43 (m, 6H, ArH), 7.23(d, J = 7.3 Hz, 1H, ArH), 6.66 (s, 1H, ArH), 6.63 (s, 1H, ArH), 5.43(s, 2H, OCH2), 3.70 (s, 6H, 2 OCH3), 3.55 (s, 2H, ArCH2N), 2.92-2.71 (m, 8H, 4 CH2); 13C NMR (75 MHz, DMSO-d6, d ppm): 28.3,32.3, 50.4, 55.0, 55.4, 59.0, 61.7, 105.8, 109.9, 111.7, 120.0, 120.4,121.7, 122.6, 124.9, 125.3, 125.8, 126.1, 126.5, 126.6, 127.4,130.0, 134.0, 134.6, 141.5, 143.9, 1468.8, 147.1, 153.4; ESI-MSm/z: 522.2 ([M+H]+); Anal. Calcd for C32H32N4O3: C, 73.82;H, 6.20; N, 10.76. Found: C, 73.87; H, 6.19; N, 10.74.

Reference： [1]Wu, Yuxiang; Pan, Miaobo; Dai, Yuxuan; Liu, Baomin; Cui, Jian; Shi, Wei; Qiu, Qianqian; Huang, Wenlong; Qian, Hai [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 10, p. 2287 - 2297]

40
[ 18542-45-5 ]
2-(2-azidoethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
6,7-dimethoxy-2-(2-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)ethyl)-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.5%	With Cu⁽²⁺⁾*CuO₄^(2-); sodium L-ascorbate In methanol at 20℃;	3 5.7.3. 6,7-Dimethoxy-2-(2-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)ethyl)-1,2,3,4-tetrahydroisoquinoline (15) General procedure: To the solution of 2d, 3d, 5d, 7d, 9d-17d (1 mmol) and c(1 mmol) in 75% methanol (40 mL), ascorbate sodium (30 mg)and CuSO4 (10 mg) were added, respectively. The reaction solutionwas stirred at room temperature for 24-48 h. Some of the reactionsolutions precipitated white solid (compound 13 and 17), theothers none. The solution with precipitate appeared filtereddirectly and the solution without precipitate appeared evaporatedin vacuo, extracted with dichloromethane. Then, the organic layerwas dried by anhydrous Na2SO4. After filtration, the solvent wasevaporated and the crude product was purified by silica gel columnchromatography using a mixture of ethyl acetate/methanol (15:1,v/v) as eluent to give the desire white solid product compounds13-25. Yield 61.5%; pale yellow powder; mp: 110-112 C; 1H NMR(300 MHz, DMSO-d6): d = 8.33 (s, 1H, NCHC), 8.07 (d, J = 7.7 Hz,1H, ArH), 7.86 (d, J = 7.5 Hz, 1H, ArH), 7.56-7.36 (m, 4H, ArH),7.15 (d, J = 7.4 Hz, 1H, ArH), 6.61 (dd, J = 13.6, 2.8 Hz, 2H, ArH),5.32 (d, J = 2.7 Hz, 2H, OCH2), 4.59 (s, 2H, CHNCH2), 3.68 (s, 6H,2 OCH3), 3.54 (s, 2H, ArCH2N), 2.92 (s, 2H, NCH2), 2.66 (s, 4H,2 CH2); 13C NMR (75 MHz, DMSO-d6, d ppm): 28.3, 32.3, 50.3,55.0, 55.6, 59.1, 61.5, 105.7, 109.7, 111.7, 120.3, 121.6, 122.5,124.8, 125.1, 125.7, 126.5, 127.3, 130.1, 134.5, 141.3, 143.8,146.8, 153.2; ESI-MS m/z: 445.0 ([M+H]+); Anal. Calcd forC26H28N4O3: C, 70.25; H, 6.35; N, 12.60. Found: C, 70.29; H, 6.34;N, 12.58.

Reference： [1]Wu, Yuxiang; Pan, Miaobo; Dai, Yuxuan; Liu, Baomin; Cui, Jian; Shi, Wei; Qiu, Qianqian; Huang, Wenlong; Qian, Hai [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 10, p. 2287 - 2297]

41
[ 18542-45-5 ]
[ 107535-12-6 ]
1-(2-isopropyl-5-methylcyclohexyl)-4-((naphthalen-1-yl oxy)-methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(II) sulfate; sodium L-ascorbate In methanol at 20℃; for 0.5h; regioselective reaction;	General Procedure for Preparation of Menthyl 1,4-Disubstituted 1,2,3-Triazole Derivatives (10a-c, 11a-i, 12a-c) General procedure: Synthesis of the target compounds 10a-c, 11a-iand 12a-cwas carried out viaalkyne-azide Huisgen cycloaddition reaction. Accordingly, propargyl ethers 7a-c, 8a-iand 9a-c(1 eq) were treated with compound 3(200 mg, 1.1 mmol) in the presence of sodium ascorbate (0.087 mg, 0.44 mmol) and copper sulfate (0.055 mg, 0.22 mmol) in MeOH (5 mL) at room temperature for 30 min to give exclusively 1,4-disubstituted 1,2,3-triazoles (10a-c, 11a-i, 12a-c). After completion of the reaction confirmed by TLC, aqueous ammonia (10 mL) was added to remove the excess of copper. In the following H2O (50 mL) was added to the suspension and extracted with EtOAc (3×50 mL). The organic layers were washed with H2O (3×150 mL) and dried over Na2SO4. Solvent was removed under reduced pressure. Final purification by flash chromatography on silica gel (25% EtOAc-n-hexane) afforded pure products in 90-98% yields.

Reference： [1]Khaligh, Pooneh; Salehi, Peyman; Bararjanian, Morteza; Aliahmadi, Atousa; Khavasi, Hamid Reza; Nejad-Ebrahimi, Samad [Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 11, p. 1589 - 1596]

42
[ 18542-45-5 ]
teicoplanin pseudoaglycon azide [ No CAS ]
C₇₉H₆₆Cl₂N₁₀O₂₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 12h;	General method B for azide-alkyne click reaction General procedure: To a stirred solution of teicoplanin pseudoaglycon azide (4) in t-butanol:water=1:1 (1 ml), an alkyne compound (1.25 equiv.), L-ascorbic acid(1.0 equiv.) and CuSO4×5 H2O (0.1 equiv.) were added and stirred forovernight at room temperature. The solvents were evaporated and the crudeproduct was purified by flash chromatography in toluene:methanol 8:2→1:1.The product obtained was passed through a column containing SephadexLH-20 gel in methanol.

Reference： [1]Szucs, Zsolt; Csávás, Magdolna; Roth, Erzsébet; Borbás, Anikó; Batta, Gyula; Perret, Florent; Ostorházi, Eszter; Szatmári, Réka; Vanderlinden, Evelien; Naesens, Lieve; Herczegh, Pál [Journal of Antibiotics, 2017, vol. 70, # 2, p. 152 - 157]

43
[ 18542-45-5 ]
[ 622-79-7 ]
1-benzyl-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃;	General procedure for the synthesis of triazole derivatives (3a-c) General procedure: Equimolar amountsof alkyne (2a-c) and benzyl azide were dissolved in tert-butanol and water (1:2) mixture. Tothis reaction mixture, copper sulphate (0.05 eq) and sodium ascorbate (0.01 eq) were addedand stirred at room temperature till the disappearance of starting materials as indicated byTLC. The reaction mixture was quenched with saturated brine and crude was extracted withethyl acetate, dried over anhyd. Na2SO4 and concentrated under vacuo. The crude was purifiedby column chromatography using dichloromethane and methanol (9:1) as eluent to give 1,2,3-triazole derivatives in good to excellent yields. The compound 3a [1-Benzyl-4-(quinolin-1-yloxy)methyl)-1H-1,2,3-triazole] has been previously reported in our lab [20].

Reference： [1]Irfan, Mohammad; Alam, Shadab; Manzoor, Nikhat; Abid, Mohammad [PLoS ONE, 2017, vol. 12, # 4]

44
[ 18542-45-5 ]
(S)-1-[1-(naphthalen-1-yloxy)allyl]-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) / 1,2-dichloro-ethane / 18 h / 60 °C / Sealed tube; Inert atmosphere

Reference： [1]Bernar, Ivan; Fiser, Béla; Blanco-Ania, Daniel; Gómez-Bengoa, Enrique; Rutjes, Floris P. J. T. [Organic Letters, 2017, vol. 19, # 16, p. 4211 - 4214]

45
[ 5326-87-4 ]
[ 18542-45-5 ]
C₂₁H₁₈N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 50 - 65℃; regioselective reaction;	General procedure for the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles7a-e, 10a-e and 13a, b, d and e General procedure: For the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles, an aqueoussolution of sodium azide (3.0/5.0 mole ratio) was added to a solution of 1.0/2.0 mole ratio of2-bromo-N-substituted acetamides 6a-e and dimethylformamide under stirring at 50-65 °C.Then, terminal alkynes 3, 9 and 12 (1.0 mmol) were added followed by addition of coppersulfate pentahydrate (1.0/2.0 mole ratio) and sodium ascorbate (1.0/2.0 mole ratio). The reactionmixture was stirred for 6-12 h at the same temperature (Schemes 1-3). After completionof the reaction, cold water was added to the reaction mixture and the precipitated solid was filteredoff and washed with aqueous ammonia solution followed by water. The crude productwas purified by washing with ethyl acetate and dried under vacuum to afford the desired 1,4--disubstituted 1,2,3-triazoles (7a-e, 10a-e and 13a, b, d and e) in good yield.

Reference： [1]Kaushik, Chander Prakash; Kumar, Krishan; Kumar, Devinder; Mor, Satbir; Kumar, Ashwani; Jindal, Deepak Kumar [Journal of the Serbian Chemical Society, 2017, vol. 82, # 9, p. 995 - 1007]

46
[ 29182-87-4 ]
[ 18542-45-5 ]
C₂₂H₂₀N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 50 - 65℃; regioselective reaction;	General procedure for the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles7a-e, 10a-e and 13a, b, d and e General procedure: For the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles, an aqueoussolution of sodium azide (3.0/5.0 mole ratio) was added to a solution of 1.0/2.0 mole ratio of2-bromo-N-substituted acetamides 6a-e and dimethylformamide under stirring at 50-65 °C.Then, terminal alkynes 3, 9 and 12 (1.0 mmol) were added followed by addition of coppersulfate pentahydrate (1.0/2.0 mole ratio) and sodium ascorbate (1.0/2.0 mole ratio). The reactionmixture was stirred for 6-12 h at the same temperature (Schemes 1-3). After completionof the reaction, cold water was added to the reaction mixture and the precipitated solid was filteredoff and washed with aqueous ammonia solution followed by water. The crude productwas purified by washing with ethyl acetate and dried under vacuum to afford the desired 1,4--disubstituted 1,2,3-triazoles (7a-e, 10a-e and 13a, b, d and e) in good yield.

Reference： [1]Kaushik, Chander Prakash; Kumar, Krishan; Kumar, Devinder; Mor, Satbir; Kumar, Ashwani; Jindal, Deepak Kumar [Journal of the Serbian Chemical Society, 2017, vol. 82, # 9, p. 995 - 1007]

47
[ 5439-13-4 ]
[ 18542-45-5 ]
C₂₁H₁₇BrN₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 50 - 65℃; regioselective reaction;	General procedure for the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles7a-e, 10a-e and 13a, b, d and e General procedure: For the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles, an aqueoussolution of sodium azide (3.0/5.0 mole ratio) was added to a solution of 1.0/2.0 mole ratio of2-bromo-N-substituted acetamides 6a-e and dimethylformamide under stirring at 50-65 °C.Then, terminal alkynes 3, 9 and 12 (1.0 mmol) were added followed by addition of coppersulfate pentahydrate (1.0/2.0 mole ratio) and sodium ascorbate (1.0/2.0 mole ratio). The reactionmixture was stirred for 6-12 h at the same temperature (Schemes 1-3). After completionof the reaction, cold water was added to the reaction mixture and the precipitated solid was filteredoff and washed with aqueous ammonia solution followed by water. The crude productwas purified by washing with ethyl acetate and dried under vacuum to afford the desired 1,4--disubstituted 1,2,3-triazoles (7a-e, 10a-e and 13a, b, d and e) in good yield.

Reference： [1]Kaushik, Chander Prakash; Kumar, Krishan; Kumar, Devinder; Mor, Satbir; Kumar, Ashwani; Jindal, Deepak Kumar [Journal of the Serbian Chemical Society, 2017, vol. 82, # 9, p. 995 - 1007]

48
[ 18542-45-5 ]
[ 3598-91-2 ]
C₂₁H₁₇N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 50 - 65℃; regioselective reaction;	General procedure for the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles7a-e, 10a-e and 13a, b, d and e General procedure: For the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles, an aqueoussolution of sodium azide (3.0/5.0 mole ratio) was added to a solution of 1.0/2.0 mole ratio of2-bromo-N-substituted acetamides 6a-e and dimethylformamide under stirring at 50-65 °C.Then, terminal alkynes 3, 9 and 12 (1.0 mmol) were added followed by addition of coppersulfate pentahydrate (1.0/2.0 mole ratio) and sodium ascorbate (1.0/2.0 mole ratio). The reactionmixture was stirred for 6-12 h at the same temperature (Schemes 1-3). After completionof the reaction, cold water was added to the reaction mixture and the precipitated solid was filteredoff and washed with aqueous ammonia solution followed by water. The crude productwas purified by washing with ethyl acetate and dried under vacuum to afford the desired 1,4--disubstituted 1,2,3-triazoles (7a-e, 10a-e and 13a, b, d and e) in good yield.

Reference： [1]Kaushik, Chander Prakash; Kumar, Krishan; Kumar, Devinder; Mor, Satbir; Kumar, Ashwani; Jindal, Deepak Kumar [Journal of the Serbian Chemical Society, 2017, vol. 82, # 9, p. 995 - 1007]

49
[ 1136-82-9 ]
[ 18542-45-5 ]
C₂₅H₂₀N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 50 - 65℃; regioselective reaction;	General procedure for the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles7a-e, 10a-e and 13a, b, d and e General procedure: For the synthesis of amide-ether-linked 1,4-disubstituted 1,2,3-triazoles, an aqueoussolution of sodium azide (3.0/5.0 mole ratio) was added to a solution of 1.0/2.0 mole ratio of2-bromo-N-substituted acetamides 6a-e and dimethylformamide under stirring at 50-65 °C.Then, terminal alkynes 3, 9 and 12 (1.0 mmol) were added followed by addition of coppersulfate pentahydrate (1.0/2.0 mole ratio) and sodium ascorbate (1.0/2.0 mole ratio). The reactionmixture was stirred for 6-12 h at the same temperature (Schemes 1-3). After completionof the reaction, cold water was added to the reaction mixture and the precipitated solid was filteredoff and washed with aqueous ammonia solution followed by water. The crude productwas purified by washing with ethyl acetate and dried under vacuum to afford the desired 1,4--disubstituted 1,2,3-triazoles (7a-e, 10a-e and 13a, b, d and e) in good yield.

Reference： [1]Kaushik, Chander Prakash; Kumar, Krishan; Kumar, Devinder; Mor, Satbir; Kumar, Ashwani; Jindal, Deepak Kumar [Journal of the Serbian Chemical Society, 2017, vol. 82, # 9, p. 995 - 1007]

50
[ 18542-45-5 ]
1-(2-azidoethyl)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole [ No CAS ]
1,8-diethyl-1-(2-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)ethyl)-1,3,4,9-tetrahydropyrano[3,4-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In dichloromethane; water at 20℃; for 6h;

Reference： [1]Kummari, Bhaskar; Polkam, Naveen; Ramesh, Perla; Anantaraju, Hasithashilpa; Yogeeswari, Perumal; Anireddy, Jaya Shree; Guggilapu, Sravanthi Devi; Babu, Bathini Nagendra [RSC Advances, 2017, vol. 7, # 38, p. 23680 - 23686]

51
[ 18542-45-5 ]
[ 84466-87-5 ]
4-((5-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper diacetate In water; <i>tert</i>-butyl alcohol at 20℃; for 8h;	General procedure for synthesis of 2-(4-((1-substituted benzyl-1H-1,2,3-tria-zol-5-yl)methoxy)-phenyl)-5-meth-yl-1,3,4-oxadiazole (21a-d).¹ General procedure: To the stirred solution of 16 (0.5 mmol), each substituted benzyl azide (20a-d)(0.5 mmol) and Cu(OAc)2 (20 mol%) in t-BuOH:H2O (3:1, 8 mL) were added and the resulting mixture was stirred at RT for 8 hrs. The reaction was monitored by TLC using EtOAc: hexanes as mobile phase. The reaction mixture was quenched with crushed ice and extracted with EtOAc (2 x 15 mL). The combined organic extracts were washed with brine (2 × 15 mL), water (50 mL) and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to afford the corresponding crude compounds. The obtained crude compounds were recrystallized from EtOH.

Reference： [1]Sahu, Niteshkumar U.; Singh, Vinayak; Ferraris, Davide M.; Rizzi, Menico; Kharkar, Prashant S. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1714 - 1718]

52
[ 90-15-3 ]
[ 624-65-7 ]
[ 18542-45-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: α-naphthol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-propynyl chloride In N,N-dimethyl-formamide for 12h;	General procedure for synthesis of prop-2-ynyl derivative (16, 18a-b). General procedure: To the stirred solution of 15/17a/17b (20 mmol) in dry DMF (20 mL), anhydrous K2CO3 (24 mmol) was added. The reaction mixture was stirred at RT for 30 min. Propargyl chloride (20 mmol) was added and stirred for 12 h. The reaction was monitored by TLC using EtOAc:hexanes as mobile phase. The reaction was quenched with crushed ice (10 g). The solid was filtered followed by recrystallization from EtOH. In case of liquid products, extraction with EtOAc (3 x 20 mL) was carried out. The combined organic layers were dried over anhydrous MgSO4. The solvent was removed under reduced pressure and used further without purification. Yield: 70-80%
	Stage #1: α-naphthol With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-propynyl chloride In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;

Reference： [1]Sahu, Niteshkumar U.; Singh, Vinayak; Ferraris, Davide M.; Rizzi, Menico; Kharkar, Prashant S. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1714 - 1718]
[2]Padhariya, Komal N.; Athavale, Maithili; Srivastava, Sangeeta; Kharkar, Prashant S. [Drug Development Research, 2021, vol. 82, # 1, p. 68 - 85]

53
[ 60923-13-9 ]
[ 18542-45-5 ]
5-hydroxy-2-((4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-4H-pyran-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; <i>tert</i>-butyl alcohol at 20℃; for 3h;	15 General procedure for the preparation of 5-hydroxy-2-{(4-(aryloxymethyl)-1H-1,2,3-triazol-1-yl)methyl}-4H-pyran-4-ones (6a-p) General procedure: Copper sulfate pentahydrate (30mg, 10mol%) and sodium ascorbate (95.1mg, 40mol%) were suspended in deoxygenated H2O (3mL) and stirred until the reaction mixture turned yellow. Then, azidokojic 3 (1.0mmol) and alkyne 5 (1.2mmol) were dissolved in THF-tert-butanol (10:1), and the solution was added to aqueous mixture containing in situ generated Cu(I). This reaction mixture was stirred for 3h at ambient temperature. After completion of the reaction (checked by TLC), the solvent was removed and the residue was dissolved in hot THF. Then, this reaction mixture was filtered and evaporated to remove solvent under reduced pressure. The residue was washed with small amount of acetone or methanol and dried in vacuo to give desired compounds 6a-p.

Reference： [1]Ashooriha, Morteza; Khoshneviszadeh, Mehdi; Khoshneviszadeh, Mahsima; Moradi, Seyed Ershad; Rafiei, Alireza; Kardan, Mostafa; Emami, Saeed [Bioorganic Chemistry, 2019, vol. 82, p. 414 - 422]

54
[ 18542-45-5 ]
[ 100-52-7 ]
4-(naphthalen-1-yloxy)-1-phenylbut-2-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 1-(propargyloxy)naphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;

Reference： [1]Zhang, Chenyun; Zhen, Long; Yao, Zhi; Jiang, Liqin [Organic Letters, 2019, vol. 21, # 4, p. 955 - 959]

55
[ 18542-45-5 ]
1-((2-ethyl-4-phenylbuta-2,3-dien-1-yl)oxy)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 2.1: dmap; triethylamine / dichloromethane / 0.17 h / 20 °C 3.1: copper(I) bromide; lithium bromide / tetrahydrofuran / 0.67 h / -40 °C / Inert atmosphere 3.2: 1 h / -40 - 0 °C / Inert atmosphere

Reference： [1]Zhang, Chenyun; Zhen, Long; Yao, Zhi; Jiang, Liqin [Organic Letters, 2019, vol. 21, # 4, p. 955 - 959]

56
[ 18542-45-5 ]
3-(but-1-en-2-yl)-2-phenylnaphtho[1,2-b]furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 2.1: dmap; triethylamine / dichloromethane / 0.17 h / 20 °C 3.1: copper(I) bromide; lithium bromide / tetrahydrofuran / 0.67 h / -40 °C / Inert atmosphere 3.2: 1 h / -40 - 0 °C / Inert atmosphere 4.1: iron(III) chloride; oxygen / N,N-dimethyl-formamide; 5,5-dimethyl-1,3-cyclohexadiene / 9 h / 120 °C / Molecular sieve; Green chemistry

Reference： [1]Zhang, Chenyun; Zhen, Long; Yao, Zhi; Jiang, Liqin [Organic Letters, 2019, vol. 21, # 4, p. 955 - 959]

57
[ 591-50-4 ]
[ 18542-45-5 ]
[ 856333-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;
	Stage #1: 1-(propargyloxy)naphthalene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 0.166667h; Inert atmosphere; Stage #2: iodobenzene at 20℃; Inert atmosphere;

Reference： [1]Fang, Jun-Dan; Yan, Xiao-Biao; Zhou, Li; Wang, Yu-Zhao; Liu, Xue-Yuan [Advanced Synthesis and Catalysis, 2019, vol. 361, # 9, p. 1985 - 1990]
[2]Fang, Jun-Dan; Yan, Xiao-Biao; Lin, Wu-Jie; Zhao, Yi-Chuan; Liu, Xue-Yuan [Organic Letters, 2019, vol. 21, # 18, p. 7635 - 7638]

58
[ 18542-45-5 ]
C₇₂H₆₆Cl₂N₁₀O₂₈ [ No CAS ]
C₈₅H₇₆Cl₂N₁₀O₂₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(ll) sulfate pentahydrate; ascorbic acid In water; <i>tert</i>-butyl alcohol at 20℃; for 12h;	Compound 4 Teicoplanin complex (1.5 g, 0.798 mmol) was dissolved in 90% aqueous TFA (15 ml) and the reaction mixture was stirred at room temperature. After 2 h, diethyl ether was added (150 ml) and the precipitate was filtered. The solid residue was washed with an additional 100 ml of diethyl ether and dried. The compound was purified by flash chromatography using a step gradient starting from acetonitrile:water = 9:1 to acetonitrile:water 75:25 (+0,1 v/v%AcOH). The yield of teicoplanin A3-1 [8] was 990 mg(78%). This material was dissolved in pyridine (40 ml), and Et3N was added (1.24 mmol, 2.0 equiv., 174 μl) followed by freshly prepared triflyl azide (1.46 mmol, 2.35 equiv.) in dry pyridine (4 ml). Then an aqueous solution of 15 mg of copper(II)-sulfate pentahydrate (2 ml) was added and the reaction mixture was stirred for 16 h at room temperature. After the addition of 300 ml ethyl acetate, a solid precipitated, which was filtered off and washed with 200 ml of ether, yielding 1.0 g of crude azido teicoplanin A3-1. This material was dissolved in a mixture of acetonitrile:water =7:3, silica gel was added, then the mixture was evaporated. The compound was purified by flash chromatography using a step gradient starting from 100% acetonitrile to acetonitrile:water 88:12 (+0,1 v/v% AcOH). The yield was 540mg. 150 mg (0.094 mmol) of this compound was dissolved in a tert-butanol:water = 1:1 mixture (2 ml). Then, 21 μl(0.118 mmol, 1.25 equiv.) of 1-(prop-2-yn-1-yloxy)naphthalene was added followed by ca. 3 mg (~15 mol%) of CuSO4×5H2O in 200 μl of water and 17 mg (0.096 mmol, 1equiv.) of L-ascorbic acid. The mixture was stirred overnight at room temperature. After the addition of silica gel, solvents were evaporated, and the product was purified by flash chromatography using a step gradient starting from acetonitrile to acetonitrile:water = 87:13 yielding 55 mg(14% for three steps) of the desired compound. NMR data and spectra can be found in the supporting information (Table S1). MALDI-TOF m/z 1793.60 [M + Na]+ (calcd.for C85H76Cl2N10NaO29+, 1793.40). Analysis calculated for C85H76Cl2N10O29 C 57.60, H 4.32, N 7.90 found: C 57.35,H 4.58, N 7.72.

Reference： [1]Szűcs, Zsolt; Ostorházi, Eszter; Kicsák, Máté; Nagy, Lajos; Borbás, Anikó; Herczegh, Pál [Journal of Antibiotics, 2019, vol. 72, # 7, p. 524 - 534]

59
[ 18542-45-5 ]
C₅₈H₄₃Cl₂N₉O₁₈ [ No CAS ]
C₇₁H₅₃Cl₂N₉O₁₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With copper(ll) sulfate pentahydrate; ascorbic acid In water; <i>tert</i>-butyl alcohol at 20℃; for 12h;	Compound 7 Teicoplanin complex of 4.00 g (2.13mmol) was heated in 90% aqueous TFA for 6 h then worked up as it is published in the literature [8], followed by treatment with TfN3 as described earlier [5]. After chromatographic purification, 450 mg(0.367mmol) of azido teicoplanin aglycon was obtained. This material was dissolved in a tert-butanol:water = 1:1 mixture(6ml). Then, 83 μl (0.46mmol, 1.25 equiv.) of 1-(prop-2-yn-1-yloxy)naphthalene was added followed by ca. 14mg(~15mol%) of CuSO4 × 5H2O in 200μl of water and 65mg (0.096mmol, 1.0 equiv.) of L-ascorbic acid in 500 μl of water. A few drops of acetonitrile was added to effect homogenity.The mixture was stirred overnight at room temperature. The reaction mixture was concentrated to a small volume and ethyl acetate was added. The precipitate was filtered off and washed with ether. The solid was dissolved in a minimum amount of acetonitrile:water = 7:3 and was loaded on acolumn containing Sephadex LH-20 in the same solvent mixture. Fractions were checked by TLC (cellulose,eluent=nPrOH:cc.NH4OH:H2O=7:3:2). Fractions containing the desired compound were pooled and concentrated to a small volume. To this, silica gel was added and the mixture was evaporated to dryness. Flash chromatography was used for further purification using a step gradient starting from acetonitrile to acetonitrile:water 93:7, yielding 255mg (49% from azido teicoplanin aglycon) of the title compound. NMR data and spectra can be found in the supporting information (Table S1). MALDI-TOF m/z 1428.09[M+Na]+ (calcd. for C71H53Cl2N9NaO19+, 1428.27). Analysiscalculated for C71H53Cl2N9O19 C 60.60, H 3.80, N 8.96found: C 60.32, H 4.04, N 8.79

Reference： [1]Szűcs, Zsolt; Ostorházi, Eszter; Kicsák, Máté; Nagy, Lajos; Borbás, Anikó; Herczegh, Pál [Journal of Antibiotics, 2019, vol. 72, # 7, p. 524 - 534]

60
benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3-di-O-acetyl-6-azido-6-deoxy-β-D-glucopyranoside [ No CAS ]
[ 18542-45-5 ]
{1-[benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3-di-O-acetyl-6-deoxy-β-D-glucopyranosid-6-yl]-1H-1,2,3-triazol-4-yl}-methanol O-α-naphthyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(II) sulfate; sodium L-ascorbate In 1,3-dioxane; water at 85℃; for 1h; Sealed tube; Microwave irradiation;	4.2. General procedure for the click reaction General procedure: Sugar derivative 6, containing an azide group at C-6 (0.21 mmol)was dissolved in dioxane (2.6 mL) in a microwave flask equipped with astirring bar. After dissolution, one of the acetylene derivatives b-t(0.23 mmol, Fig. S1) was added. Then, sodium ascorbate (0.23 mmol),CuSO4 (0.11 mmol) and water (0.48 mL) were added and the tube wassealed. The mixture was stirred at 85 °C (5 W) for 1 h in the microwave,unless stated otherwise. The reaction was followed by TLC and aftercompletion, the solvent was evaporated and the residue chromatographedin a silica gel column (toluene/ethyl acetate as mobile phase).Yields ranged between 85 and 96% (For a complete characterization ofproducts 15b-15r see Supporting information).

Reference： [1]Morrone-Pozzuto, Pablo; Uhrig, Maria Laura; Agusti, Rosalia [Carbohydrate Research, 2019, vol. 478, p. 33 - 45]

61
[ 18542-45-5 ]
[ 35634-10-7 ]
1-((3-(3-methylenecyclobutylidene)allyl)oxy)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; diethyl ether at -20 - 20℃; for 1h;

Reference： [1]Lasányi, Dániel; Tolnai, Gergely L. [Organic Letters, 2019, vol. 21, # 24, p. 10057 - 10062]

62
[ 6921-27-3 ]
[ 90-15-3 ]
[ 18542-45-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In acetone; toluene at 20℃;

Reference： [1]Lasányi, Dániel; Tolnai, Gergely L. [Organic Letters, 2019, vol. 21, # 24, p. 10057 - 10062]

63
[ 18542-45-5 ]
3-[(E)-chloromethylidene]-2,3-dihydronaphtho[1,2-b][1,4]-oxaselenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With selenium(II) chloride In methanol; chloroform at -60 - 20℃; for 8.25h; stereoselective reaction;

Reference： [1]Musalov, Maxim V.; Yakimov, Vladimir A.; Potapov, Vladimir A.; Amosova, Svetlana V.; Borodina, Tatyana N.; Zinchenko, Sergey V. [New Journal of Chemistry, 2019, vol. 43, # 47, p. 18476 - 18483]

64
[ 18542-45-5 ]
3-[(E)-bromomethylidene]-2,3-dihydronaphtho[1,2-b][1,4]-oxaselenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With selenium dibromide In methanol; chloroform at -60 - 20℃; for 8.25h; stereoselective reaction;

Reference： [1]Musalov, Maxim V.; Yakimov, Vladimir A.; Potapov, Vladimir A.; Amosova, Svetlana V.; Borodina, Tatyana N.; Zinchenko, Sergey V. [New Journal of Chemistry, 2019, vol. 43, # 47, p. 18476 - 18483]

65
1-azidoferrocene [ No CAS ]
[ 18542-45-5 ]
C₂₃H₁₉FeN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃;	2.6. Synthesis of receptors 1-4 General procedure: Triazolylferrocene derivative (1.0 mmol), 1-(prop-2-yn-1-yloxy)naphthalene [43] or 8-(prop-2-yn-1-yloxy)quinoline [44] (1.0 mmol)and tetrahydrofuran (THF, 20 mL) were placed into a flask and stirredto dissolve, then the aqueous solution (8 mL) of sodium ascorbate(4.0 mmol, 0.78 g) as well as aqueous solution (6 mL) of CuSO4•5H2O(0.32 g, 2.0 mmol) were slowly added at ambient temperature, respectively.After stirring overnight, the substrate was treated with NH4OH(10 mL), then extracted using dichloromethane two times. The combinedorganic phaseswerewashedwith brine andwater, dried over anhydrousMgSO4and concentrated in vacuo. The residuewas purified by column chromatography over silica gel eluted with CH2Cl2/EtOAc (4:1,V:V). Receptor 1, m.p.179-183 °C, yield 85%, Rf=0.21(EtOAc/CH2Cl2 1:4,V:V); 1H NMR (CDCl3, 500MHz) (δ ppm): 8.28 (s, 1H, napthol), 7.82 (d,2H, J = 7.0 Hz, napthol), 7.49 (d, 2H, J = 6.0 Hz, napthol), 7.47 (s, 1H,triazole), 7.40 (t, 1H, J = 6.6 Hz, napthol), 6.99 (d, 1H, J = 6.5 Hz,napthol), 5.45 (s, 2H, CH2), 4.98 (s, 2H, Cp), 4.41 (s, 2H, Cp), 4.34 (s,5H, Cp); 13C NMR (CDCl3, 125 MHz) (δ ppm): 153.97, 144.31, 134.61,127.58, 126.51, 125.85, 125.74, 125.35, 122.34, 121.99, 121.00, 105.68,93.69, 70.20, 66.74, 62.22; FTIR (KBr, ν, cm-1) 3090, 2922, 1628, 1459,1096, 1054, 765, 496; ESI-TOF HRMS, m/z: [M]+ for C23H19FeN3O:Calcd 409.0872, found 409.0867.

Reference： [1]Xu, Jianwei; Yang, Yongqiang; Baigude, Huricha; Zhao, Haiying [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 229]

66
1-(azidomethyl)ferrocene [ No CAS ]
[ 18542-45-5 ]
C₂₄H₂₁FeN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃;	2.6. Synthesis of receptors 1-4 General procedure: Triazolylferrocene derivative (1.0 mmol), 1-(prop-2-yn-1-yloxy)naphthalene [43] or 8-(prop-2-yn-1-yloxy)quinoline [44] (1.0 mmol)and tetrahydrofuran (THF, 20 mL) were placed into a flask and stirredto dissolve, then the aqueous solution (8 mL) of sodium ascorbate(4.0 mmol, 0.78 g) as well as aqueous solution (6 mL) of CuSO4•5H2O(0.32 g, 2.0 mmol) were slowly added at ambient temperature, respectively.After stirring overnight, the substrate was treated with NH4OH(10 mL), then extracted using dichloromethane two times. The combinedorganic phaseswerewashedwith brine andwater, dried over anhydrousMgSO4and concentrated in vacuo. The residuewas purified by column chromatography over silica gel eluted with CH2Cl2/EtOAc (4:1,V:V).

Reference： [1]Xu, Jianwei; Yang, Yongqiang; Baigude, Huricha; Zhao, Haiying [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 229]

67
[ 18542-45-5 ]
[ 352-11-4 ]
[ 1286706-53-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium azide; C₃₂H₄₅BCuN₄PS₂ In water at 60℃; for 0.916667h; Green chemistry;	2.2. General procedure for the “Click” synthesis of 1,4-Disubstitude 1,2,3-Triazoles General procedure: A mixture of organic halide or epoxide (1.0 mmol), sodium azide(1.2 mmol), and alkyne (1.0 mmol) was stirred in water (3.0 mL) assolvent. Then, Cu(Bb)(PCy3) (5 mg) was added to the reaction mixtureand it was further stirred at 60 °C for a period of time. After completionof the reaction (monitored by TLC), the reaction mixture was extractedby ethyl acetate (5 mL, 3 times) and dried over anhydrous Na2SO4 andthe procedure was followed by concentration under reduced pressure.The crude products were purified by column chromatography on silicagel (silica gel, n-hexane-EtOAc) to give the pure products.

Reference： [1]Khalili, Dariush; Evazi, Roya; Neshat, Abdollah; Aboonajmi, Jasem; Osanlou, Farzane [Inorganica Chimica Acta, 2020, vol. 506]

68
[ 18542-45-5 ]
[ 874-86-2 ]
4-((4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium azide; C₃₂H₄₅BCuN₄PS₂ In water at 60℃; for 1.16667h; Green chemistry;	2.2. General procedure for the “Click” synthesis of 1,4-Disubstitude 1,2,3-Triazoles General procedure: A mixture of organic halide or epoxide (1.0 mmol), sodium azide(1.2 mmol), and alkyne (1.0 mmol) was stirred in water (3.0 mL) assolvent. Then, Cu(Bb)(PCy3) (5 mg) was added to the reaction mixtureand it was further stirred at 60 °C for a period of time. After completionof the reaction (monitored by TLC), the reaction mixture was extractedby ethyl acetate (5 mL, 3 times) and dried over anhydrous Na2SO4 andthe procedure was followed by concentration under reduced pressure.The crude products were purified by column chromatography on silicagel (silica gel, n-hexane-EtOAc) to give the pure products.

Reference： [1]Khalili, Dariush; Evazi, Roya; Neshat, Abdollah; Aboonajmi, Jasem; Osanlou, Farzane [Inorganica Chimica Acta, 2020, vol. 506]

69
[ 18542-45-5 ]
[ 456-41-7 ]
1-(3-fluorobenzyl)-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium azide In water at 90℃; for 2h;	General procedure for the synthesis of 1,2,3-triazoles from halides in thepresence of a catalytic amount of the spinel CuAl2O4 NPs General procedure: Alkyl and benzyl halide (1 mmol), terminal alkyne (1.1 mmol) and sodium azide (1.2 mmol)were mixed and stirred in water (3 mL) in the presence of the CuAl2O4 catalyst (0.005g) at 90°C in a 10 mL round-bottom flask. After completion of the reaction (as monitored by TLC usingn-hexane/ethyl acetate), the catalyst was separated by simple filtration. The filtrate was dilutedwith H2O (5 mL) and extracted with EtOAc (3×10 mL). The combined organic phases werewashed with brine and dried over anhydrous Na2SO4, and the volatiles were removed underreduced pressure. The resulting residue was purified by column chromatography using nhexane-ethyl acetate (10:1 to 10:6) as the eluent, to provide pure 1,4-disubstituted-1,2,3-triazolederivatives.
85%	With sodium azide; C₃₂H₄₅BCuN₄PS₂ In water at 60℃; for 1.33333h; Green chemistry;	2.2. General procedure for the “Click” synthesis of 1,4-Disubstitude 1,2,3-Triazoles General procedure: A mixture of organic halide or epoxide (1.0 mmol), sodium azide(1.2 mmol), and alkyne (1.0 mmol) was stirred in water (3.0 mL) assolvent. Then, Cu(Bb)(PCy3) (5 mg) was added to the reaction mixtureand it was further stirred at 60 °C for a period of time. After completionof the reaction (monitored by TLC), the reaction mixture was extractedby ethyl acetate (5 mL, 3 times) and dried over anhydrous Na2SO4 andthe procedure was followed by concentration under reduced pressure.The crude products were purified by column chromatography on silicagel (silica gel, n-hexane-EtOAc) to give the pure products.

Reference： [1]Kavoosi, Leila; Khalafi-Nezhad, Ali; Khalili, Dariush [Synlett, 2019, vol. 30, # 19, p. 2136 - 2142]
[2]Khalili, Dariush; Evazi, Roya; Neshat, Abdollah; Aboonajmi, Jasem; Osanlou, Farzane [Inorganica Chimica Acta, 2020, vol. 506]

70
[ 18542-45-5 ]
[ 106-95-6 ]
1-allyl-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium azide; C₃₂H₄₅BCuN₄PS₂ In water at 60℃; for 0.833333h; Green chemistry;	2.2. General procedure for the “Click” synthesis of 1,4-Disubstitude 1,2,3-Triazoles General procedure: A mixture of organic halide or epoxide (1.0 mmol), sodium azide(1.2 mmol), and alkyne (1.0 mmol) was stirred in water (3.0 mL) assolvent. Then, Cu(Bb)(PCy3) (5 mg) was added to the reaction mixtureand it was further stirred at 60 °C for a period of time. After completionof the reaction (monitored by TLC), the reaction mixture was extractedby ethyl acetate (5 mL, 3 times) and dried over anhydrous Na2SO4 andthe procedure was followed by concentration under reduced pressure.The crude products were purified by column chromatography on silicagel (silica gel, n-hexane-EtOAc) to give the pure products.
88%	With sodium azide In water at 90℃; for 1.5h;	General procedure for the synthesis of 1,2,3-triazoles from halides in thepresence of a catalytic amount of the spinel CuAl2O4 NPs General procedure: Alkyl and benzyl halide (1 mmol), terminal alkyne (1.1 mmol) and sodium azide (1.2 mmol)were mixed and stirred in water (3 mL) in the presence of the CuAl2O4 catalyst (0.005g) at 90°C in a 10 mL round-bottom flask. After completion of the reaction (as monitored by TLC usingn-hexane/ethyl acetate), the catalyst was separated by simple filtration. The filtrate was dilutedwith H2O (5 mL) and extracted with EtOAc (3×10 mL). The combined organic phases werewashed with brine and dried over anhydrous Na2SO4, and the volatiles were removed underreduced pressure. The resulting residue was purified by column chromatography using nhexane-ethyl acetate (10:1 to 10:6) as the eluent, to provide pure 1,4-disubstituted-1,2,3-triazolederivatives.

Reference： [1]Khalili, Dariush; Evazi, Roya; Neshat, Abdollah; Aboonajmi, Jasem; Osanlou, Farzane [Inorganica Chimica Acta, 2020, vol. 506]
[2]Kavoosi, Leila; Khalafi-Nezhad, Ali; Khalili, Dariush [Synlett, 2019, vol. 30, # 19, p. 2136 - 2142]

71
[ 96-09-3 ]
[ 18542-45-5 ]
2-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-2-phenylethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium azide; C₃₂H₄₅BCuN₄PS₂ In water at 60℃; for 1.16667h; Green chemistry;	2.2. General procedure for the “Click” synthesis of 1,4-Disubstitude 1,2,3-Triazoles General procedure: A mixture of organic halide or epoxide (1.0 mmol), sodium azide(1.2 mmol), and alkyne (1.0 mmol) was stirred in water (3.0 mL) assolvent. Then, Cu(Bb)(PCy3) (5 mg) was added to the reaction mixtureand it was further stirred at 60 °C for a period of time. After completionof the reaction (monitored by TLC), the reaction mixture was extractedby ethyl acetate (5 mL, 3 times) and dried over anhydrous Na2SO4 andthe procedure was followed by concentration under reduced pressure.The crude products were purified by column chromatography on silicagel (silica gel, n-hexane-EtOAc) to give the pure products.

Reference： [1]Khalili, Dariush; Evazi, Roya; Neshat, Abdollah; Aboonajmi, Jasem; Osanlou, Farzane [Inorganica Chimica Acta, 2020, vol. 506]

72
[ 18542-45-5 ]
[ 100-39-0 ]
1-benzyl-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium azide In water at 90℃; for 2h;	General procedure for the synthesis of 1,2,3-triazoles from halides in thepresence of a catalytic amount of the spinel CuAl2O4 NPs General procedure: Alkyl and benzyl halide (1 mmol), terminal alkyne (1.1 mmol) and sodium azide (1.2 mmol)were mixed and stirred in water (3 mL) in the presence of the CuAl2O4 catalyst (0.005g) at 90°C in a 10 mL round-bottom flask. After completion of the reaction (as monitored by TLC usingn-hexane/ethyl acetate), the catalyst was separated by simple filtration. The filtrate was dilutedwith H2O (5 mL) and extracted with EtOAc (3×10 mL). The combined organic phases werewashed with brine and dried over anhydrous Na2SO4, and the volatiles were removed underreduced pressure. The resulting residue was purified by column chromatography using nhexane-ethyl acetate (10:1 to 10:6) as the eluent, to provide pure 1,4-disubstituted-1,2,3-triazolederivatives.
93%	With sodium azide; C₃₂H₄₅BCuN₄PS₂ In water at 60℃; for 0.75h; Green chemistry;	2.2. General procedure for the “Click” synthesis of 1,4-Disubstitude 1,2,3-Triazoles General procedure: A mixture of organic halide or epoxide (1.0 mmol), sodium azide(1.2 mmol), and alkyne (1.0 mmol) was stirred in water (3.0 mL) assolvent. Then, Cu(Bb)(PCy3) (5 mg) was added to the reaction mixtureand it was further stirred at 60 °C for a period of time. After completionof the reaction (monitored by TLC), the reaction mixture was extractedby ethyl acetate (5 mL, 3 times) and dried over anhydrous Na2SO4 andthe procedure was followed by concentration under reduced pressure.The crude products were purified by column chromatography on silicagel (silica gel, n-hexane-EtOAc) to give the pure products.

Reference： [1]Kavoosi, Leila; Khalafi-Nezhad, Ali; Khalili, Dariush [Synlett, 2019, vol. 30, # 19, p. 2136 - 2142]
[2]Khalili, Dariush; Evazi, Roya; Neshat, Abdollah; Aboonajmi, Jasem; Osanlou, Farzane [Inorganica Chimica Acta, 2020, vol. 506]

73
[ 18542-45-5 ]
[ 93246-53-8 ]
4-(2-fluoro-4-(4-([naphthalen-1-yloxy]methyl)-1H-1,2,3-triazol-1-yl)phenyl)morpholine [ No CAS ]