Science Journal of Chemistry
Volume 5, Issue 4, August 2017, Pages: 58-61
Received: Jul. 2, 2017;
Accepted: Jul. 12, 2017;
Published: Aug. 30, 2017
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Saleem Farooq, Department of Chemistry, Govt. Degree College (Boys), Baramulla, India
Bashir Ahmad Dar, Department of Chemistry, Govt. Degree College (Boys), Sopore, India
Mushtaq Ahmad Tantaray, Department of Chemistry, Govt. Degree College (Boys), Baramulla, India
Mushtaq Ahmad Lone, Department of Chemistry, Govt. Degree College (Boys), Baramulla, India
Nuzhat Rehman, Department of Chemistry, Govt. Degree College (Boys), Baramulla, India
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.
Bashir Ahmad Dar,
Mushtaq Ahmad Tantaray,
Mushtaq Ahmad Lone,
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.
Vol. 5, No. 4,
2017, pp. 58-61.
Corey, E. J; Cheng, X. M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989.
(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.
(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.
Zeni, G; Panatieri, R. B; Lissner, E; Menezes, P. H; Braga, A. L; Stefani, H. A. Org. Lett. 2001, 3, 819.
Stutz, A. Angew. Chem., Int. Ed. 1987, 26, 320.
Paixao, M. W; Weber, M; Braga, A. L; Azeredo, J. B; Deobald, A. M; Stefani, H. A. Tetrahedron Lett. 2008, 49, 2366.
(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.
Siemsen, P; Livingston, R. C; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
Inouchi, K; Kabashi, S; Takimiya, K; Aso, Y; Otsubo, T. Org. Lett. 2002, 4, 2533.
(a) Hay, A. J. Org. Chem. 1960, 25, 1275; (b) Hay, A. S. J. Org. Chem. 1962, 27, 3320.
(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.
(a) Liu, Q; Burton, D. J. Tetrahedron Lett. 1997, 38, 4371; (b) Lei, A; Srivastava, M; Zhang, X. J. Org. Chem. 2002, 67, 1969.
D. Li; K. Yin; J. Li; X. S. Jia; Tetrahedron Lett. 2008, 49, 5918.
(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.
X. Niu; C. Li; J. Li; X. Jia; Tetrahedron Lett. 2012, 53, 5559.
(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.
(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.
(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.
Hopkinson, M. N; Antony, D. Gee; Gouverneur, V; Chem. Eur. J. 2011, 17, 8248-8262.
Gonzalez-Arellano, C; Abad, A; Corma, A; Garcia, H; Iglesias, M; Sanchez, F. Angew. Chem. Int. Ed. 2007, 46, 1536.
Mei, Zhu; Ma, Ning; Weijun, Fu; Chen, Xu; Guanglong, Zou. Bull. Korean Chem. Soc. 2012, 33, 1325.
Shi, W; Lei, A; Tetrahedron Lett. 2014, 55, 2763-2772.
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.
(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.
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.