Name: 18750-95-3|9,10-Bis((trimethylsilyl)ethynyl)anthracene|95%
Brand: Ambeed
SKU: A2272695
Rating: 95 (32 reviews)

1
[ 75-77-4 ]
C₁₈H₈Br₂Mg₂ [ No CAS ]
[ 18750-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at 20 - 50℃;

Reference： [1]Le Quan Minh et al. [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1960, vol. 251, p. 730 - 732]

2
[ 18750-95-3 ]
[ 189034-90-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride In acetic acid at 80℃; for 3h;

Reference： [1]Scott, Lawrence T.; Necula, Atena [Tetrahedron Letters, 1997, vol. 38, # 11, p. 1877 - 1880]

3
[ 523-27-3 ]
[ 1066-54-2 ]
[ 18750-95-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With copper (I) iodide; cis-dichlorobis(triphenylphosphine) palladium(II); N,N-diisopropylamine In tetrahydrofuran for 8h; Reflux;
97%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine In tetrahydrofuran for 8h; Reflux;
95%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N-ethylethanamine at 70℃; for 22h; Inert atmosphere; Reflux;

95%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N-ethylethanamine for 20h; Inert atmosphere;
88%	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In toluene for 48h; Reflux; Inert atmosphere;	9,10-dibromoanthracene (1.00 g, 2.98 mmol) and trimethylsilyl-acetylene (1.17 g, 11.92 mmol) were added to toluene (110 mL). Triethylamine (25 mL) was added and then tetrakis(triphenyl-phosphine)palladium (0) (70 mg, 0.06 mmol) and copper iodide (23 mg, 0.12 mmol) were added. The mixture was degassed and then heated at reflux for 48 hours with vigorous stirring under nitrogen. The solvent was removed in a rotary evaporator and the resulting mixture was poured into water and extracted with dichloromethane, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated to dryness. The crude product was purified by column chromatography (silica gel) using petroleum ether as eluent to yield ared solid (0.97 g, 88%). 1H NMR (300 MHz, CDCl3, δ, ppm): 8.57 (dd, J=6.6 and 3.0 Hz, 4H, Ar), 7.59 (dd, J=6.6 and 3.3 Hz, 4H, Ar), 0.43 (s,18H, SiCH3).
87%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine In tetrahydrofuran at 60℃;
85%	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In tetrahydrofuran at 60℃; for 20h; Inert atmosphere;
85%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine In tetrahydrofuran for 8h; Inert atmosphere; Reflux;
85%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine In tetrahydrofuran for 8h; Inert atmosphere; Reflux;
84%	Stage #1: 9,10-Dibromoanthracene With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In tetrahydrofuran for 0.333333h; Inert atmosphere; Stage #2: trimethylsilylacetylene In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;
81%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine In tetrahydrofuran at 80℃; for 16h; Inert atmosphere;
63%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine; triphenylphosphine In toluene at 85℃; for 16h; Inert atmosphere;	Synthesis of compound 3 CuI (0.15 g, 0.79 mmol), Pd(PPh3)2Cl2 (0.23 g, 0.33 mmol), PPh3 (0.1 g, 0.38 mmol),9,10-dibromoanthracene (2.02 g, 6.01 mmol), and TMSA (1.9 g, 19.34 mmol) were dissolved ina mixture of toluene (20 mL) and diisopropylamine (8 mL) in a 100 mL three-necked flaskunder N2 atmosphere. After stirring for 16 h at 85 , the resulting mixture was extracted withdiethyl ether. The organic layer was collected and washed with saturated NaHCO3 solution,then dried over anhydrous MgSO4. Column chromatography was applied with the hexane aseluent to purify the product (1.31 g, 63%, yellow powder). 1H NMR (400 MHz, CDCl3, 298 K),δ (ppm): 8.581 (d, 4H), 7.614 (d, 4H), 0.422 (s, 18H). 13C NMR (100 MHz, CDCl3, 298 K): δ(ppm) 132.044, 126.996, 125.652, 118.239, 107.970, 101.281, 77.128, 77.015, 76.810, 76.493.
60%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; triphenylphosphine for 12h; Reflux; Inert atmosphere;
50%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide In tetrahydrofuran at 70℃; for 24h; Inert atmosphere;
48%	With triethylamine; triphenylphosphine
45%	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine for 3h; Inert atmosphere; Reflux;
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N-ethylethanamine
	With copper (I) iodide
	With copper (I) iodide; cis-dichlorobis(triphenylphosphine) palladium(II); triethylamine; triphenylphosphine
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine for 72h; Reflux;
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran Inert atmosphere;
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux;
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 60℃; for 3h; Inert atmosphere;

Reference： [1]Fudickar, Werner; Linker, Torsten [Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13661 - 13664]
[2]Fudickar, Werner; Linker, Torsten [Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 15071 - 15082]
[3]Kaleta, Jiří; Dron, Paul I.; Zhao, Ke; Shen, Yongqiang; Císařová, Ivana; Rogers, Charles T.; Michl, Josef [Journal of Organic Chemistry, 2015, vol. 80, # 12, p. 6173 - 6192]
[4]Kaleta, Jiří; Kaletová, Eva; Císařová, Ivana; Teat, Simon J.; Michl, Josef [Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10134 - 10150]
[5]Zhu, Jikai; Zhong, Keli; Liang, Yongri; Wang, Zhuoshi; Chen, Tie; Jin, Long Yi [Tetrahedron, 2014, vol. 70, # 6, p. 1230 - 1235]
[6]Göstl; Sijbesma [Chemical Science, 2016, vol. 7, # 1, p. 370 - 375]
[7]Location in patent: experimental part Ou, Ya-Ping; Jiang, Chuanyin; Wu; Xia, Jianlong; Yin, Jun; Jin, Shan; Yu, Guang-Ao; Liu, Sheng Hua [Organometallics, 2011, vol. 30, # 21, p. 5763 - 5770]
[8]Nonomura, Kohei; Yuasa, Junpei [Inorganic Chemistry, 2019, vol. 58, # 9, p. 6474 - 6484]
[9]Iseki, Shuta; Kishida, Sakura; Nonomura, Kohei; Ogata, Daiji; Yuasa, Junpei [Journal of the American Chemical Society, 2020, vol. 142, # 37, p. 15842 - 15851]
[10]Slodek, Aneta; Filapek, Michal; Schab-Balcerzak, Ewa; Grucela, Marzena; Kotowicz, Sonia; Janeczek, Henryk; Smolarek, Karolina; Mackowski, Sebastian; Malecki, Jan Grzegorz; Jedrzejowska, Agnieszka; Szafraniec-Gorol, Grazyna; Chrobok, Anna; Marcol, Beata; Krompiec, Stanislaw; Matussek, Marek [European Journal of Organic Chemistry, 2016, vol. 2016, # 23, p. 4020 - 4031]
[11]Gao, Hong-Ying; Held, Philipp Alexander; Amirjalayer, Saeed; Liu, Lacheng; Timmer, Alexander; Schirmer, Birgitta; Díaz Arado, Oscar; Mönig, Harry; Mück-Lichtenfeld, Christian; Neugebauer, Johannes; Studer, Armido; Fuchs, Harald [Journal of the American Chemical Society, 2017, vol. 139, # 20, p. 7012 - 7019]
[12]Wang, Dinghui; Wang, Jun; Wang, Yan; Yang, Yingwei [Molecules, 2022, vol. 27, # 10]
[13]Location in patent: experimental part Shanmugaraju, Sankarasekaran; Joshi, Sachin A.; Mukherjee, Partha Sarathi [Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9130 - 9138]
[14]Goudappagouda; Wakchaure, Vivek Chandrakant; Ranjeesh, Kayaramkodath Chandran; Abhai, Chalona Antony Ralph; Babu, Sukumaran Santhosh [Chemical Communications, 2017, vol. 53, # 52, p. 7072 - 7075]
[15]Scott, Lawrence T.; Necula, Atena [Tetrahedron Letters, 1997, vol. 38, # 11, p. 1877 - 1880]
[16]Colella, Silvia; Mazzeo, Marco; Grisorio, Roberto; Fabiano, Eduardo; Melcarne, Giovanna; Carallo, Sonia; Angione, M. Daniela; Torsi, Luisa; Suranna, Gian Paolo; Della Sala, Fabio; Mastrorilli, Piero; Gigli, Giuseppe [Chemical Communications, 2010, vol. 46, # 34, p. 6273 - 6275]
[17]Matsumi; Naka; Chujo [Journal of the American Chemical Society, 1998, vol. 120, # 20, p. 5112 - 5113]
[18]Caskey, Douglas C.; Wang, Bing; Zheng, Xiaolai; Michl, Josef [Collection of Czechoslovak Chemical Communications, 2005, vol. 70, # 11, p. 1970 - 1985]
[19]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - EP1170273, 2002, A1 Location in patent: Page 11
[20]Gole, Bappaditya; Shanmugaraju, Sankarasekaran; Bar, Arun Kumar; Mukherjee, Partha Sarathi [Chemical Communications, 2011, vol. 47, # 36, p. 10046 - 10048]
[21]Lamm, Jan-Hendrik; Glatthor, Johanna; Weddeling, Jan-Henrik; Mix, Andreas; Chmiel, Jasmin; Neumann, Beate; Stammler, Hans-Georg; Mitzel, Norbert W. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7355 - 7365]
[22]Mishra, Veenu; Raghuvanshi, Abhinav; Saini, Anoop Kumar; Mobin, Shaikh M. [Journal of Organometallic Chemistry, 2016, vol. 813, p. 103 - 109]
[23]Wang, Guangxia; Xiao, Hongmei; He, Jiaojiao; Xiang, Junfeng; Wang, Ying; Chen, Xuebo; Che, Yanke; Jiang, Hua [Journal of Organic Chemistry, 2016, vol. 81, # 8, p. 3364 - 3371]
[24]Tarkuç, Simge; Eelkema, Rienk; Grozema, Ferdinand C. [Tetrahedron, 2017, vol. 73, # 33, p. 4994 - 5004]

4
[ 18750-95-3 ]
[ 18512-55-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With lithium hydroxide monohydrate; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h;	Compound 5 (1.00 mg, 2.98 mmol) was dissolved in a mixture of methanol (80 mL) and tetrahydrofuran (40 mL) and then potassium hydroxide (10%, 15 mL) was added to the solution. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed in a rotary evaporator and there sulting mixture was poured into water and extracted with ether, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated to dryness. The crude product was purified by column chromatography (silica gel) using petroleum ether as eluent to yield a yellow grey cotton-shaped solid (0.75 g, 90%). 1H NMR (300 MHz, CDCl3, δ, ppm): 8.61 (dd, J=6.6 and 3.0 Hz, 4H, Ar), 7.62 (dd, J=6.6 and 3.3 Hz, 4H, Ar), 4.07 (s, 2H, C≡C-H).
88%	With sodium hydroxide In methanol; diethyl ether; lithium hydroxide monohydrate at 20℃; for 4h; Inert atmosphere;	Synthesis of 9,10-diethynylanthracene [S2] Compound 3 (2.0 g, 5.40 mmol), 300 mL fresh diethyl ether, 200 mL methanol, and 100mL NaOH (1 M) aqueous solution were charged sequentially into a 1000 mL three-neckedflask under an N2 atmosphere. The reaction mixture was stirred for 4 h at room temperature.The resulting mixture was extracted with diethyl ether. The obtained organic solution wasdried over anhydrous MgSO4. After evaporation, the product was recrystallized from hexane.(1.08 g, 88%, yellow crystal). 1H NMR (400 MHz, CDCl3, 298 K), δ (ppm): 8.621 (d, 4H), 7.631(d, 4H), 4.070 (s, 2H).
76%	With potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h;

72%	With potassium fluoride
66%	With methanol; potassium hydroxide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
40%	With potassium fluoride In methanol; dichloromethane for 12h; Inert atmosphere; Reflux;
25%	With methanol; potassium carbonate at 20℃;
	With methanol; potassium hydroxide In tetrahydrofuran
	With methanol; potassium hydroxide In tetrahydrofuran Inert atmosphere;
	With potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h; Inert atmosphere;
	With potassium hydroxide In tetrahydrofuran; methanol at 25℃;
	With potassium fluoride In tetrahydrofuran; methanol at 60℃; for 3h; Inert atmosphere; Schlenk technique;	Synthesis of S,S′-((anthracene-9,10-diylbis (ethyne-2,1-diyl))bis(4,1-phenylene)) diethanethioate, 7a A solution of 9,10-bis((trimethylsilyl)ethynyl)anthracene (100 mg, 0.269 mmol) and KF (40 mg, 0.673 mmol) in a solution of dry, degassed MeOH (10 mL) and THF (5 mL), was stirred at 60°C temperature for 3 h. After this time the reaction mixture was allowed to cool, and the solvent was removed under reduced pressure. The residue was treated with dry, degassed NEt3 (10 mL) and THF (2 mL), S-(4-iodophenyl) ethanethioate (157 mg, 0.565 mmol), [PdCl2(PPh3)2] (10 mg, 0.013 mmol) and CuI (3 mg, 0.013 mmol), and the mixture allowed to stirred at room temperature for further 2 h. After this time, the solvent removed in vacuo, and the residue purified by column chromatography on silica eluting with CH2Cl2:hexane (1:8) followed by CH2Cl2:hexane (1:3) to give the product as a yellow solid. Yield was 0.85 g (60%). IR (solid state, ATR)/cm-1: ν(C≡C) 2113. 1H NMR (CDCl3, 500 MHz, δ/ppm): 8.67 (dd, J = 6.6, 3.3 Hz, 4H, H11), 7.81 (d, J = 8.4 Hz, 4H, H5), 7.66 (dd, J = 6.6, 3.3 Hz, 4H, H12), 7.51 (d, J = 8.4 Hz, 4H, H4), 2.48 (s, 6H, H1). 13C{1H} NMR (CDCl3, 126 MHz, δ/ppm): 193.54 (C2), 134.60 (C3), 132.38 (C5), 132.31 (C10), 128.77 (C6), 127.33 (C11), 127.19 (C12), 124.70 (C4), 118.54 (C9), 101.86 (C7), 88.27 (C8), 30.50 (C1). Acc-MS(ESI+): m/z 526.1069 [M]+ calculated for C34H22O2S2 526.1061

Reference： [1]Zhu, Jikai; Zhong, Keli; Liang, Yongri; Wang, Zhuoshi; Chen, Tie; Jin, Long Yi [Tetrahedron, 2014, vol. 70, # 6, p. 1230 - 1235]
[2]Wang, Dinghui; Wang, Jun; Wang, Yan; Yang, Yingwei [Molecules, 2022, vol. 27, # 10]
[3]Khan, Muhammad S.; Al-Mandhary, Muna R. A.; Al-Suti, Mohammed K.; Al-Battashi, Fathiya R.; Al-Saadi, Sultan; Ahrens, Birte; Bjernemose, Jens K.; Mahon, Mary F.; Raithby, Paul R.; Younus, Muhammad; Chawdhury, Nazia; Koehler, Anna; Marseglia, Elizabeth A.; Tedesco, Emilio; Feeder, Neil; Teat, Simon J. [Dalton Transactions, 2004, # 15, p. 2377 - 2385]
[4]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - EP1170273, 2002, A1 Location in patent: Page 11
[5]Location in patent: experimental part Ou, Ya-Ping; Jiang, Chuanyin; Wu; Xia, Jianlong; Yin, Jun; Jin, Shan; Yu, Guang-Ao; Liu, Sheng Hua [Organometallics, 2011, vol. 30, # 21, p. 5763 - 5770]
[6]Colella, Silvia; Mazzeo, Marco; Grisorio, Roberto; Fabiano, Eduardo; Melcarne, Giovanna; Carallo, Sonia; Angione, M. Daniela; Torsi, Luisa; Suranna, Gian Paolo; Della Sala, Fabio; Mastrorilli, Piero; Gigli, Giuseppe [Chemical Communications, 2010, vol. 46, # 34, p. 6273 - 6275]
[7]Lamm, Jan-Hendrik; Glatthor, Johanna; Weddeling, Jan-Henrik; Mix, Andreas; Chmiel, Jasmin; Neumann, Beate; Stammler, Hans-Georg; Mitzel, Norbert W. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7355 - 7365]
[8]Gole, Bappaditya; Shanmugaraju, Sankarasekaran; Bar, Arun Kumar; Mukherjee, Partha Sarathi [Chemical Communications, 2011, vol. 47, # 36, p. 10046 - 10048]
[9]Mishra, Veenu; Raghuvanshi, Abhinav; Saini, Anoop Kumar; Mobin, Shaikh M. [Journal of Organometallic Chemistry, 2016, vol. 813, p. 103 - 109]
[10]Goudappagouda; Wakchaure, Vivek Chandrakant; Ranjeesh, Kayaramkodath Chandran; Abhai, Chalona Antony Ralph; Babu, Sukumaran Santhosh [Chemical Communications, 2017, vol. 53, # 52, p. 7072 - 7075]
[11]Tarkuç, Simge; Eelkema, Rienk; Grozema, Ferdinand C. [Tetrahedron, 2017, vol. 73, # 33, p. 4994 - 5004]
[12]Becker, Thomas; Gorenskaia, Elena; Lambert, Colin J.; Low, Paul J.; Moggach, Stephen A.; Naher, Masnun; Nichols, Richard J. [Australian Journal of Chemistry, 2022]

5
[ 113705-11-6 ]
[ 1066-54-2 ]
[ 18750-95-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 9,10-diiodoanthracene With copper(l) iodide; isopropylamine; triphenylphosphine In tetrahydrofuran Stage #2: trimethylsilylacetylene In tetrahydrofuran Further stages.;

Reference： [1]Khan, Muhammad S.; Al-Mandhary, Muna R. A.; Al-Suti, Mohammed K.; Al-Battashi, Fathiya R.; Al-Saadi, Sultan; Ahrens, Birte; Bjernemose, Jens K.; Mahon, Mary F.; Raithby, Paul R.; Younus, Muhammad; Chawdhury, Nazia; Koehler, Anna; Marseglia, Elizabeth A.; Tedesco, Emilio; Feeder, Neil; Teat, Simon J. [Dalton Transactions, 2004, # 15, p. 2377 - 2385]

6
9,10-dihydro-9,10-bis[(trimethylsilyl)ethynyl]-9,10-anthracenediol [ No CAS ]
[ 18750-95-3 ]

Yield	Reaction Conditions	Operation in experiment
39%	With tin(ll) chloride In ethanol; water; acetic acid at 60℃;

Reference： [1]Lydon, Donocadh P.; Porres, Laurent; Beeby, Andrew; Marder, Todd B.; Low, Paul J. [New Journal of Chemistry, 2005, vol. 29, # 7, p. 972 - 976]

7
[ 18750-95-3 ]
[ 118-92-3 ]
9,10-bis[(trimethylsilyl)ethynyl]triptycene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	Stage #1: anthranilic acid With isopentyl nitrite In 1,2-dimethoxyethane Heating; Stage #2: 9,10-bis(trimethylsilyl)ethynylanthracene In 1,2-dimethoxyethane Heating;
23%	With isopentyl nitrite In 1,2-dimethoxyethane at 100℃; for 26h; Inert atmosphere;
23%	With isopentyl nitrite In 1,2-dimethoxyethane at 100℃; for 22h; Inert atmosphere;

Reference： [1]Caskey, Douglas C.; Wang, Bing; Zheng, Xiaolai; Michl, Josef [Collection of Czechoslovak Chemical Communications, 2005, vol. 70, # 11, p. 1970 - 1985]
[2]Kaleta, Jiří; Dron, Paul I.; Zhao, Ke; Shen, Yongqiang; Císařová, Ivana; Rogers, Charles T.; Michl, Josef [Journal of Organic Chemistry, 2015, vol. 80, # 12, p. 6173 - 6192]
[3]Kaleta, Jiří; Kaletová, Eva; Císařová, Ivana; Teat, Simon J.; Michl, Josef [Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10134 - 10150]

8
[ 523-27-3 ]
[ 18750-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; diethyl ether / 0.67 h 1.2: 50 percent / iodine / hexane; diethyl ether / 0.33 h 2.1: ⁱPrNH₂; CuI; PPh₃ / Pd(OAc)2 / tetrahydrofuran 2.2: 78 percent / tetrahydrofuran

Reference： [1]Khan, Muhammad S.; Al-Mandhary, Muna R. A.; Al-Suti, Mohammed K.; Al-Battashi, Fathiya R.; Al-Saadi, Sultan; Ahrens, Birte; Bjernemose, Jens K.; Mahon, Mary F.; Raithby, Paul R.; Younus, Muhammad; Chawdhury, Nazia; Koehler, Anna; Marseglia, Elizabeth A.; Tedesco, Emilio; Feeder, Neil; Teat, Simon J. [Dalton Transactions, 2004, # 15, p. 2377 - 2385]

9
[ 18750-95-3 ]
[ 131581-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 86 percent / conc. HCl / acetic acid / 3 h / 80 °C 2: 900 °C / 1 Torr

Reference： [1]Scott, Lawrence T.; Necula, Atena [Tetrahedron Letters, 1997, vol. 38, # 11, p. 1877 - 1880]

10
[ 18750-95-3 ]
Cyclopent[h,i]acephananthrylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 86 percent / conc. HCl / acetic acid / 3 h / 80 °C 2: 900 °C / 1 Torr 3: 1100 °C / 1 Torr

Reference： [1]Scott, Lawrence T.; Necula, Atena [Tetrahedron Letters, 1997, vol. 38, # 11, p. 1877 - 1880]

11
ammonium hexafluorophosphate [ No CAS ]
[ 204995-23-3 ]
[ 18750-95-3 ]
[(Ru(2,2'-bipyridine)2(C₆H₃C₅H₄NCC))2C₁₄H₈][PF₆]2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With Pd(P(C₆H₅)3)4; CuI; NaOH In N,N-dimethyl-formamide soln. of Ru complex, Pd(PPh3)4/CuI as catalyst and bis-trimethylsilylethynylarene in DMF heated under Ar for 15 h with 1 pellet of NaOH; sepd. by chromy. on silica gel (MeCN/toluene, 1:1); solvent removed (vac.); NH4PF6 and MeCN added; soln. stirred; soln. evapd. to dryness; dissolved (CH2Cl2); PF6 salt deposited on preparative TLC plate; eluted (MeCN/toluene, 4:6); complex desorbed from silica by soaking in concd. soln. of NH4PF6 in MeCN; solvent removed; dissolved in CH2Cl2; concd.; Et2O added;

Reference： [1]Fraysse, Sandrine; Coudret, Christophe; Launay, Jean-Pierre [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5880 - 5888]

12
ammonium hexafluorophosphate [ No CAS ]
[ 541548-63-4 ]
[ 18750-95-3 ]
[(Ru(4,4'-di-tert-butyl-2,2'-bipyridine)2(C₆H₃C₅H₄NCC))2C₁₄H₈][PF₆]2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With Pd(P(C₆H₅)3)4; CuI; NaOH In N,N-dimethyl-formamide soln. of Ru complex, Pd(PPh3)4/CuI as catalyst and bis-trimethylsilylethynylarene in DMF heated under Ar for 15 h with 1 pellet of NaOH; sepd. by chromy. on silica gel (MeCN/toluene, 1:1); solvent removed (vac.); NH4PF6 and MeCN added; soln. stirred; soln. evapd. to dryness; dissolved (CH2Cl2); PF6 salt deposited on preparative TLC plate; eluted (CH2Cl2, CH2Cl2/MeOH); complex desorbed from silica by soaking in concd. soln. of NH4PF6 in MeCN; solvent removed; dissolved in CH2Cl2; concd.; Et2O added;

Reference： [1]Fraysse, Sandrine; Coudret, Christophe; Launay, Jean-Pierre [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5880 - 5888]

13
chloro(η5-cyclopentadienyl)(1,1'-bis(diphenylphosphino)ferrocene)ruthenium(II) [ No CAS ]
[ 18750-95-3 ]
[((C₅H₅)(1,1'-bis(diphenylphosphino)ferrocene)Ru)2(1,4-anthracenediyl)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	In tetrahydrofuran; methanol (Ar); std. Schlenk technique; diyne and KF were added to MeOH/THF (5/1);Ru complex was added; soln. was stirred under reflux for 1 d; solvent evapd. (vac.); chromd. (alumina, CH2Cl2); petroleum ether layered into CH2Cl2 soln.; elem. anal.;

Reference： [1]Gao, Li-Bin; Zhang, Li-Yi; Shi, Lin-Xi; Chen, Zhong-Ning [Organometallics, 2005, vol. 24, # 7, p. 1678 - 1684]

14
(1,2,3,4,5-pentamethylcyclopentadienyl)(1,2-bis(diphenylphosphino)ethane)iron(II)Cl [ No CAS ]
[ 75-09-2 ]
[ 18750-95-3 ]
[((C₅Me₅)Fe(1,2-bis(diphenylphosphino)ethane))2(9,10-bis(ethynyl)anthracene)]*CH₂Cl₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With K₂CO₃; NaBPh₄; t-BuOK In methanol (Ar); Schlenk technique; soln. of C14H8(CCSiMe3)2 in methanol was stirred in presence of K2CO3 (2.2 equiv.) for 10 h; Fe complex (2.2 equiv.) and NaBPh4 (2.2 equiv.) were added; stirred for 16 h; BuOK (2.2 equiv.) was added; stirred for 4 h; solvent removed; extd. (toluene); concd.; pentane added; ppt. washed (pentane); dried; elem. anal.;

Reference： [1]De Montigny, Frederic; Argouarch, Gilles; Costuas, Karine; Halet, Jean-Francois; Roisnel, Thierry; Toupet, Loic; Lapinte, Claude [Organometallics, 2005, vol. 24, # 19, p. 4558 - 4572]

15
pentamethylcyclopentadienyl(1,2-bis(diphenylphosphino)ethane)chlororuthenium(II) [ No CAS ]
[ 18750-95-3 ]
[(Ru(dppe)Cp*)2(μ-9,10-diethynylanthracene)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With KF In methanol (N2); refluxing a mixt. of Ru complex, alkyne, KF in methanol for 40 h; filtration, washing ppt. with methanol, hexane, drying;

Reference： [1]Fox, Mark A.; Le Guennic, Boris; Roberts, Rachel L.; Brue, Daniel A.; Yufit, Dmitry S.; Howard, Judith A. K.; Manca, Gabriele; Halet, Jean-Francois; Hartl, Frantisek; Low, Paul J. [Journal of the American Chemical Society, 2011, vol. 133, # 45, p. 18433 - 18446]

16
[ 623-00-7 ]
[ 18750-95-3 ]
[ 136809-42-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; potassium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 5h;
54%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide for 5h;

Reference： [1]Fudickar, Werner; Linker, Torsten [Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13661 - 13664]
[2]Fudickar, Werner; Linker, Torsten [Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 15071 - 15082]

17
[ 619-42-1 ]
[ 18750-95-3 ]
9,10-bis(4-methoxycarbonylphenylethynyl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; potassium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 5h;
61%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide for 5h;

Reference： [1]Fudickar, Werner; Linker, Torsten [Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13661 - 13664]
[2]Fudickar, Werner; Linker, Torsten [Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 15071 - 15082]

18
[ 18750-95-3 ]
[ 1122-91-4 ]
[ 1361119-48-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; potassium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide at 80℃; for 5h;
55%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide for 5h;

Reference： [1]Fudickar, Werner; Linker, Torsten [Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13661 - 13664]
[2]Fudickar, Werner; Linker, Torsten [Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 15071 - 15082]

19
[ 18750-95-3 ]
9,10-bis(4-trimethylsilylphenyethynyl)-9,10-dihydro-9,10-epidioxyanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With oxygen; methylene blue In chloroform at -20℃; for 24h; Irradiation;

Reference： [1]Fudickar, Werner; Linker, Torsten [Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 15071 - 15082]

20
[ 104-92-7 ]
[ 18750-95-3 ]
[ 80034-27-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide

Reference： [1]Fudickar, Werner; Linker, Torsten [Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 15071 - 15082]

21
[ 3972-65-4 ]
[ 18750-95-3 ]
[ 1268850-46-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide

Reference： [1]Fudickar, Werner; Linker, Torsten [Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 15071 - 15082]

22
[ 18750-95-3 ]
C₆₄H₇₀O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide; water / methanol; tetrahydrofuran / 2 h / 20 °C 2: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / tetrahydrofuran / 48 h / Reflux; Inert atmosphere

Reference： [1]Zhu, Jikai; Zhong, Keli; Liang, Yongri; Wang, Zhuoshi; Chen, Tie; Jin, Long Yi [Tetrahedron, 2014, vol. 70, # 6, p. 1230 - 1235]

23
[ 18750-95-3 ]
[ 1586804-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide; water / methanol; tetrahydrofuran / 2 h / 20 °C 2: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / tetrahydrofuran / 48 h / Reflux; Inert atmosphere

Reference： [1]Zhu, Jikai; Zhong, Keli; Liang, Yongri; Wang, Zhuoshi; Chen, Tie; Jin, Long Yi [Tetrahedron, 2014, vol. 70, # 6, p. 1230 - 1235]

24
[ 18750-95-3 ]
C₄₈H₅₂Si₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform-d1 UV-irradiation;

Reference： [1]Lamm, Jan-Hendrik; Glatthor, Johanna; Weddeling, Jan-Henrik; Mix, Andreas; Chmiel, Jasmin; Neumann, Beate; Stammler, Hans-Georg; Mitzel, Norbert W. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7355 - 7365]

25
[ 1585-90-6 ]
[ 18750-95-3 ]
C₃₀H₃₃NO₃Si₂ [ No CAS ]

Reference： [1]Chemical Science,2016,vol. 7,p. 370 - 375

26
[ 18750-95-3 ]
C₃₆H₂₅NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: m-xylene / 72 h / 150 °C 2: potassium carbonate / tetrahydrofuran; methanol / 2 h / 20 °C 3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / tetrahydrofuran / 24 h / 20 °C

Reference： [1]Göstl; Sijbesma [Chemical Science, 2016, vol. 7, # 1, p. 370 - 375]

27
[ 18750-95-3 ]
C₄₄H₃₅Br₂NO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: m-xylene / 72 h / 150 °C 2: potassium carbonate / tetrahydrofuran; methanol / 2 h / 20 °C 3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / tetrahydrofuran / 24 h / 20 °C 4: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C

Reference： [1]Göstl; Sijbesma [Chemical Science, 2016, vol. 7, # 1, p. 370 - 375]

28
[ 18750-95-3 ]
C₂₄H₁₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: m-xylene / 72 h / 150 °C 2: potassium carbonate / tetrahydrofuran; methanol / 2 h / 20 °C

Reference： [1]Göstl; Sijbesma [Chemical Science, 2016, vol. 7, # 1, p. 370 - 375]

29
[ 18750-95-3 ]
(Ph3PAuI)2-9,10-anthracenyldiacetylide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: methanol; potassium hydroxide / tetrahydrofuran / Inert atmosphere 2: sodium ethanolate / ethanol / 1 h / Reflux; Inert atmosphere

Reference： [1]Mishra, Veenu; Raghuvanshi, Abhinav; Saini, Anoop Kumar; Mobin, Shaikh M. [Journal of Organometallic Chemistry, 2016, vol. 813, p. 103 - 109]

30
[ 18750-95-3 ]
[ 4661-46-5 ]
9,10-bis[(trimethylsilyl)ethynyl]triptycene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With methyloxirane In 1,2-dichloro-ethane for 24h; Reflux;

Reference： [1]Wang, Guangxia; Xiao, Hongmei; He, Jiaojiao; Xiang, Junfeng; Wang, Ying; Chen, Xuebo; Che, Yanke; Jiang, Hua [Journal of Organic Chemistry, 2016, vol. 81, # 8, p. 3364 - 3371]

31
[ 18750-95-3 ]
C₉H₉N₂O₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]
2,3-dimethyl-9,10-bis((trimethylsilyl)ethynyl)triptycene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With methyloxirane In 1,2-dichloro-ethane for 24h; Reflux;

Reference： [1]Wang, Guangxia; Xiao, Hongmei; He, Jiaojiao; Xiang, Junfeng; Wang, Ying; Chen, Xuebo; Che, Yanke; Jiang, Hua [Journal of Organic Chemistry, 2016, vol. 81, # 8, p. 3364 - 3371]

32
[Ag₂(μ-bis(diphenylphosphino)methane)₂(MeCN)₂](BF₄)₂ [ No CAS ]
[ 18750-95-3 ]
C₁₆₈H₁₄₀Ag₆P₁₂⁽⁴⁺⁾*4BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium fluoride In tetrahydrofuran; methanol at 20℃; for 24h; Inert atmosphere; Schlenk technique;	[{Ag3(μ-dppm)3(μ3-η1-C≡C)}2An-9,10](BF4)4 General procedure: A mixture of [Ag2(μ-dppm)2(MeCN)2](BF4)2 (100 mg,0.08 mmol) and 9,10-bis(trimethylsilylethynyl)anthracene (9.9 mg,0.026 mmol) in the presence of an excess of potassium fluoride(7 mg, 0.12 mmol) in tetrahydrofuran/methanol (20:1 v/v, 21 mL)was stirred at room temperature for 24 h. After evaporation todryness, the solid residue was extracted with dichloromethane.Recrystallization from layering of n-hexane onto a concentrateddichloromethane solution of the crude products afforded 1 as anorange solid. Yield: 70 mg, 74%. 1H NMR (400 MHz, acetone-d6,298 K, relative to SiMe4)/ppm: δ 3.49-3.51 (m, 6H, CH2),3.88-3.90 (m, 6H, CH2), 6.63-7.40 (m, 120H, C6H5), 7.62-7.65(m, 4H, An), 8.65-8.69 (m, 4H, An). 31P{1H} NMR (162 MHz,acetone-d6, 298 K, relative to 85% H3PO4)/ppm: δ 0.72, 2.95 (d,JAgP 361 Hz). Positive ESI-MS:m/z 1674 [M-2BF4]2+. IR (KBr disc,ν/cm-1): 2168 (m), ν(C≡C). Elemental analyses. Found (%): C 57.18,H 4.06. Calcd for 1: C 57.24, H, 4.00.

Reference： [1]Lo, Hiu-Suet; Chung-Chin Cheng, Eddie; Xu, Hong-Liang; Lam, Wai Han; Zhu, Nianyong; Ka-Man Au, Vonika; Yam, Vivian Wing-Wah [Journal of Organometallic Chemistry, 2016, vol. 812, p. 43 - 50]

33
[ 120-12-7 ]
[ 18750-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: bromine / chloroform / 4 h / 20 °C 2.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.33 h / Inert atmosphere 2.2: 24 h / 60 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: bromine; acetic acid 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 3 h / 60 °C / Inert atmosphere

Reference： [1]Slodek, Aneta; Filapek, Michal; Schab-Balcerzak, Ewa; Grucela, Marzena; Kotowicz, Sonia; Janeczek, Henryk; Smolarek, Karolina; Mackowski, Sebastian; Malecki, Jan Grzegorz; Jedrzejowska, Agnieszka; Szafraniec-Gorol, Grazyna; Chrobok, Anna; Marcol, Beata; Krompiec, Stanislaw; Matussek, Marek [European Journal of Organic Chemistry, 2016, vol. 2016, # 23, p. 4020 - 4031]
[2]Tarkuç, Simge; Eelkema, Rienk; Grozema, Ferdinand C. [Tetrahedron, 2017, vol. 73, # 33, p. 4994 - 5004]

34
[ 18750-95-3 ]
2-iodo-7-(9H-carbazol-9-yl)-9,9-dibutylfluorene [ No CAS ]
9,10--(9H-carbazol-9-yl)-9,9-dibutylfluoren-2-yl]ethynyl}-anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;

Reference： [1]Slodek, Aneta; Filapek, Michal; Schab-Balcerzak, Ewa; Grucela, Marzena; Kotowicz, Sonia; Janeczek, Henryk; Smolarek, Karolina; Mackowski, Sebastian; Malecki, Jan Grzegorz; Jedrzejowska, Agnieszka; Szafraniec-Gorol, Grazyna; Chrobok, Anna; Marcol, Beata; Krompiec, Stanislaw; Matussek, Marek [European Journal of Organic Chemistry, 2016, vol. 2016, # 23, p. 4020 - 4031]

35
[ 18750-95-3 ]
9,9-dibutyl-N,N-diphenyl-7-iodo-9H-fluoren-2-amine [ No CAS ]
9,10--(N,N-diphenylamino)-9,9-dibutylfluoren-2-yl]-ethynyl}anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;

Reference： [1]Slodek, Aneta; Filapek, Michal; Schab-Balcerzak, Ewa; Grucela, Marzena; Kotowicz, Sonia; Janeczek, Henryk; Smolarek, Karolina; Mackowski, Sebastian; Malecki, Jan Grzegorz; Jedrzejowska, Agnieszka; Szafraniec-Gorol, Grazyna; Chrobok, Anna; Marcol, Beata; Krompiec, Stanislaw; Matussek, Marek [European Journal of Organic Chemistry, 2016, vol. 2016, # 23, p. 4020 - 4031]

36
[ 1403934-60-0 ]
[ 18750-95-3 ]
9,10--(9H-carbazol-9-yl)-9-butylcarbazol-3-yl]ethynyl}-anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;

Reference： [1]Slodek, Aneta; Filapek, Michal; Schab-Balcerzak, Ewa; Grucela, Marzena; Kotowicz, Sonia; Janeczek, Henryk; Smolarek, Karolina; Mackowski, Sebastian; Malecki, Jan Grzegorz; Jedrzejowska, Agnieszka; Szafraniec-Gorol, Grazyna; Chrobok, Anna; Marcol, Beata; Krompiec, Stanislaw; Matussek, Marek [European Journal of Organic Chemistry, 2016, vol. 2016, # 23, p. 4020 - 4031]

37
[ 18750-95-3 ]
[ 1361119-48-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide / tetrahydrofuran; methanol / 25 °C 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / Inert atmosphere