Homocoupling of terminal alkynes to 1, 3-diynes has been investigated, using AuCl3 as catalyst under mild and operationally simple conditions. Effect of different organic and inorganic bases on the product yield and the reaction time were also studied. The catalyst is efficient, furnishes good to excellent yield of the desired products with organic bases and Sodium acetate was found to be the most effective base under solvent free conditions at room temperature.
| Published in | Science Journal of Chemistry (Volume 5, Issue 4) |
| DOI | 10.11648/j.sjc.20170504.13 |
| Page(s) | 58-61 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2017. Published by Science Publishing Group |
Gold Trichloride, Homocoupling, Terminal Alkyne, Diyne
| [1] | Corey, E. J; Cheng, X. M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989. |
| [2] | (a) Nicolaou, K. C; Petasis, N. A; Zipkin, R. E; Uenishi, J. J. Am. Chem. Soc. 1982, 104, 5555; (b) Shi Shun, A. L. K; Tykwinski, R. R. Angew. Chem., Int. Ed. 2006, 45, 1034. |
| [3] | (a) Mayer, S. F; Steinreiber, A; Orru, R. V. A; Faber, K. J. Org. Chem. 2002, 67, 9115; (b) Ratnayake, A. S; Hemscheidt, T. Org. Lett. 2002, 4, 4667; (c) Yun, H. Danishefsky, S. J. J. Org. Chem. 2003, 68, 4519. |
| [4] | Zeni, G; Panatieri, R. B; Lissner, E; Menezes, P. H; Braga, A. L; Stefani, H. A. Org. Lett. 2001, 3, 819. |
| [5] | Stutz, A. Angew. Chem., Int. Ed. 1987, 26, 320. |
| [6] | Paixao, M. W; Weber, M; Braga, A. L; Azeredo, J. B; Deobald, A. M; Stefani, H. A. Tetrahedron Lett. 2008, 49, 2366. |
| [7] | (a) A. Domenech; A. Leyva-Perez, S. I; Al-Resayes, A. Corma, Electrochem. Commun. 2012, 19, 145; (b) Y. N. Li; J. L. Wang; L. N. He; Tetrahedron Lett. 2011, 52, 3485; (c) H. A. Stefani; A. S. Guarezemini; R. Cella. Tetrahedron, 2010, 66, 7871. |
| [8] | Siemsen, P; Livingston, R. C; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632. |
| [9] | Inouchi, K; Kabashi, S; Takimiya, K; Aso, Y; Otsubo, T. Org. Lett. 2002, 4, 2533. |
| [10] | (a) Hay, A. J. Org. Chem. 1960, 25, 1275; (b) Hay, A. S. J. Org. Chem. 1962, 27, 3320. |
| [11] | (a) Jiang, H. F; Tang, J. Y; Wang, A. Z; Deng, G. H; Yang, S. R. Synthesis, 2006, 1155; (b) Kamata, K; Yamaguchi, S; Kotani, M; Yamaguchi, K; Mizuno, N. Angew. Chem., Int. Ed. 2008, 47, 2407; (c) Adimurthy, S; Malakar, C. C; Beifuss, U. J. Org. Chem. 2009, 74, 5648; (d) Yin, W; He, C; Chen, M; Zhang, H; Lei, A. Org. Lett. 2009, 11, 709; (e) Chen, Z; Jiang, H; Wang, A; Yang, S. J. Org. Chem. 2010, 75, 6700; (f) Yadav, J. S; Reddy, B. V. S; R. Bhaskar, R, K; Uma Gayathri, K; Prasad, A. R. Tetrahedron Lett. 2003, 44, 6493; (g) Li, L; Wang, J; Zhang, G; Liu, Q. Tetrahedron Lett. 2009, 50, 4033. |
| [12] | (a) Liu, Q; Burton, D. J. Tetrahedron Lett. 1997, 38, 4371; (b) Lei, A; Srivastava, M; Zhang, X. J. Org. Chem. 2002, 67, 1969. |
| [13] | D. Li; K. Yin; J. Li; X. S. Jia; Tetrahedron Lett. 2008, 49, 5918. |
| [14] | (a) X. Jia; K. Yin; C. Li; J. Li; H. B; Green Chem. 2011, 13, 2175;(b) K. Yin; C. Li; J. Li; X. Jia; Green Chem. 2011, 13, 591-593. |
| [15] | X. Niu; C. Li; J. Li; X. Jia; Tetrahedron Lett. 2012, 53, 5559. |
| [16] | (a) Cahiez, G; Moyeux, A; Buendia, J; Duplais, C. J. Am. Chem. Soc. 2007, 129, 13788; (b) Bharathi, P; Periasamy, M. Organometallics, 2000, 19, 5511. |
| [17] | (a) Hashmi, A. S. K; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896; (b) Zhang, L; Sun, J; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271. (c) Furstner, A; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410; (d) Jimenez-Nunez, E; Echavarren, A. M. Chem. Commun. 2007, 333; (e) Gorin, D. J; Toste, F. D. Nature 2007, 446, 395; (f) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180; (g) Marion, N; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750; (h) Hashmi, A. S. K. Nature, 2007, 449, 292. |
| [18] | (a) Shapiro, N. D; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244; (b) Barluenga, J; Dieguez, A; Fernandez, A; Rodriguez, F; Fananas, F. J. Angew. Chem., Int. Ed. 2006, 45, 2091; (c) Buzas, A; Gagosz, F. Synlett 2006, 2727. (d) Hashmi, A. S. K; Salathe, R; Frey, W. Synlett, 2007, 1763. |
| [19] | Hopkinson, M. N; Antony, D. Gee; Gouverneur, V; Chem. Eur. J. 2011, 17, 8248-8262. |
| [20] | Gonzalez-Arellano, C; Abad, A; Corma, A; Garcia, H; Iglesias, M; Sanchez, F. Angew. Chem. Int. Ed. 2007, 46, 1536. |
| [21] | Mei, Zhu; Ma, Ning; Weijun, Fu; Chen, Xu; Guanglong, Zou. Bull. Korean Chem. Soc. 2012, 33, 1325. |
| [22] | Shi, W; Lei, A; Tetrahedron Lett. 2014, 55, 2763-2772. |
| [23] | Dar, B. A; D. Vyas; V. Shrivastava; S. Farooq; A. Sharma; S. Sharma; P. R. Sharma; M. Sharma; B. Singh; C. R. Chimie, 2014, 17, 316. |
| [24] | (a) Dar, B. A; Singh, S; Pandey, N; Singh, A. P; Sharma, P; Lazar, A; Sharma, M; Vishwakarma, R. A; Singh B. Appl. Catal. A: Gen., 2014, 470, 232; (b) Dar, B. A; Syed, N. A; Wagay, M. A; Hussain A; Ahmad, N; Bhat, K. A; Khuroo, M. A; Sharma, M; Singh, B. Tetrahedron Lett. 2013, 54, 4880; (c) Dar, B. A; Singh, A; Sahu, A; Patidar, P; Chakraborty, A; Sharma, M; Singh, B. Tetrahedron Lett. 2012, 53, 5497. |
| [25] | General Procedure: To 4-tolylacetylene 1(1eq.), Sodium acetate (1.2 equiv) using as base, was added and the contents were stirred for 5 minutes, followed by the addition of AuCl3 (5 mol %) as the catalyst in solvent free conditions afforded the desired product. The reaction mixture was then allowed to stirr at room temperature for 30 minutes. On completion of the reaction (monitored by TLC). The reaction was worked up by dilution with water followed by solvent ethyl acetate. The contents of the reaction mixture were extracted with ethyl acetate (3×50ml), the organic layer washed with water (3×20ml) and dried over anhydrous sodium sulphate and concentrated on rot-vapor to give crude product, which on column chromatography over silica gel (mesh 60–120) using hexane and ethyl acetate (19:1) as eluent to obtain product. |
APA Style
Saleem Farooq, Bashir Ahmad Dar, Mushtaq Ahmad Tantaray, Mushtaq Ahmad Lone, Nuzhat Rehman. (2017). Gold Chloride (AuCl3) Catalyzed Expeditious Homocoupling of Terminal Alkynes at Ambient and Solvent Free Conditions: Impact of Sodium Acetate on the Reaction Yield. Science Journal of Chemistry, 5(4), 58-61. https://doi.org/10.11648/j.sjc.20170504.13
ACS Style
Saleem Farooq; Bashir Ahmad Dar; Mushtaq Ahmad Tantaray; Mushtaq Ahmad Lone; Nuzhat Rehman. Gold Chloride (AuCl3) Catalyzed Expeditious Homocoupling of Terminal Alkynes at Ambient and Solvent Free Conditions: Impact of Sodium Acetate on the Reaction Yield. Sci. J. Chem. 2017, 5(4), 58-61. doi: 10.11648/j.sjc.20170504.13
AMA Style
Saleem Farooq, Bashir Ahmad Dar, Mushtaq Ahmad Tantaray, Mushtaq Ahmad Lone, Nuzhat Rehman. Gold Chloride (AuCl3) Catalyzed Expeditious Homocoupling of Terminal Alkynes at Ambient and Solvent Free Conditions: Impact of Sodium Acetate on the Reaction Yield. Sci J Chem. 2017;5(4):58-61. doi: 10.11648/j.sjc.20170504.13
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Download@article{10.11648/j.sjc.20170504.13,
author = {Saleem Farooq and Bashir Ahmad Dar and Mushtaq Ahmad Tantaray and Mushtaq Ahmad Lone and Nuzhat Rehman},
title = {Gold Chloride (AuCl3) Catalyzed Expeditious Homocoupling of Terminal Alkynes at Ambient and Solvent Free Conditions: Impact of Sodium Acetate on the Reaction Yield},
journal = {Science Journal of Chemistry},
volume = {5},
number = {4},
pages = {58-61},
doi = {10.11648/j.sjc.20170504.13},
url = {https://doi.org/10.11648/j.sjc.20170504.13},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20170504.13},
abstract = {Homocoupling of terminal alkynes to 1, 3-diynes has been investigated, using AuCl3 as catalyst under mild and operationally simple conditions. Effect of different organic and inorganic bases on the product yield and the reaction time were also studied. The catalyst is efficient, furnishes good to excellent yield of the desired products with organic bases and Sodium acetate was found to be the most effective base under solvent free conditions at room temperature.},
year = {2017}
}
TY - JOUR T1 - Gold Chloride (AuCl3) Catalyzed Expeditious Homocoupling of Terminal Alkynes at Ambient and Solvent Free Conditions: Impact of Sodium Acetate on the Reaction Yield AU - Saleem Farooq AU - Bashir Ahmad Dar AU - Mushtaq Ahmad Tantaray AU - Mushtaq Ahmad Lone AU - Nuzhat Rehman Y1 - 2017/08/30 PY - 2017 N1 - https://doi.org/10.11648/j.sjc.20170504.13 DO - 10.11648/j.sjc.20170504.13 T2 - Science Journal of Chemistry JF - Science Journal of Chemistry JO - Science Journal of Chemistry SP - 58 EP - 61 PB - Science Publishing Group SN - 2330-099X UR - https://doi.org/10.11648/j.sjc.20170504.13 AB - Homocoupling of terminal alkynes to 1, 3-diynes has been investigated, using AuCl3 as catalyst under mild and operationally simple conditions. Effect of different organic and inorganic bases on the product yield and the reaction time were also studied. The catalyst is efficient, furnishes good to excellent yield of the desired products with organic bases and Sodium acetate was found to be the most effective base under solvent free conditions at room temperature. VL - 5 IS - 4 ER -
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