Abstract
A novel methodology for the one-pot synthesis of unsymmetrical 1,3-butadiynes directly by the reaction of calcium carbide with aryl iodides is reported. This reaction system uses a safe, inexpensive, and easily handled acetylene source, and is easy to manipulate. This protocol is not only highly productive and selective, but also tolerates a wide range of functional groups.
REFERENCES
Tang, J.L. and Zhao, X.M., RSC Adv., 2012, vol. 2, p. 5488. https://doi.org/10.1039/c2ra20326j
Zhang, G.T., Yi, H., Chen, H., Bian, C.L., Liu, C., and Lei, A.W., Org. Lett., 2014, vol. 16, p. 6156. https://doi.org/10.1021/ol503015b
Jiang, H.F., Zeng, W., Li, Y.B., Wu, W.Q., Huang, L.B., and Wei, F., J. Org. Chem., 2012, vol. 77, p. 5179. https://doi.org/10.1021/jo300692d
Kramer, S., Madsen, J.L.H., Rottlander, M., and Skrydstrup, T., Org. Lett., 2010, vol. 12, p. 2758. https://doi.org/10.1021/ol1008685
Zheng, Q., Hua, R., Jiang, J., and Zhang, L., Tetrahedron, 2014, vol. 70, no. 44, p. 8252. https://doi.org/10.1016/j.tet.2014.09.025
Matsuda, T., Kadowaki, S., and Murakami, T., Chem. Commun., 2007, vol. 25, p. 2627. https://doi.org/10.1039/b703397d
Carmichael, D., Ricard, L., and Mathey, F., J. Chem. Soc., 1994, vol. 10, p. 1167. https://doi.org/10.1039/C39940001167
Ewa, P.D., Ludmiła, S., and Lechosław, L.G., Chem. Eur. J., 2011, vol. 17, p. 3500. https://doi.org/10.1002/chem.201002765
Ahmad, S., Yadav, K.K., Bhattacharya, S., Chauhan, P., and Chauhan, S.M.S., J. Org. Chem., 2015, vol. 80, p. 3880. https://doi.org/10.1021/acs.joc.5b00007
Alves, D., Luchese, C., Nogueira, C.W., and Zeni, G., J. Org. Chem., 2007, vol. 72, p. 6726. https://doi.org/10.1021/jo070835t
Lerch, M.L., Harper, M.K., and Faulkner, D.J., J. Nat. Prod., 2003, vol. 66, p. 667. https://doi.org/10.1021/np020544%2B
Zhou, Y.Z., Ma, H.Y., Chen, H., Qiao, L., Yao, Y., Cao, J.Q., and Pei, Y.H., Chem. Pharm. Bull., 2006, vol. 54, p. 1455. https://doi.org/10.1248/cpb.54.1455
Mayer, S.F., Steinreiber, A., Orru, R.V.A., and Faber, K., J. Org. Chem., 2002, vol. 67, p. 9115. https://doi.org/10.1021/jo020073w
Zeni, G., Panatieri, R.B., Lissner, E., Menezes, P.H., Braga, A.L., and Stefani, H.A., Org. Lett., 2001, vol. 3, p. 819. https://doi.org/10.1021/ol006946v
Hay, A.S., J. Org. Chem., 1962, vol. 27, p. 3320. https://doi.org/10.1021/jo01056a511
Hay, A.S., J. Org. Chem., 1960, vol. 25, p. 1275. https://doi.org/10.1021/jo01077a633
Chemistry of Acetylenes, Cadiot, P., Chodkiewicz, W., and Viehe, H.G., Eds. New York: Marcel Dekker, 1969, p. 597.
Nishihara, Y., Ikegashira, K., Mori, A., and Hiyama, T., Tetrahedron Lett., 1998, vol. 39, p. 4075. https://doi.org/10.1016/S0040-4039(98)00662-5
Kang, S.K., Baik, T.G., Jiao, X.H., and Lee, Y.T., Tetrahedron Lett., 1999, vol. 40, p. 2383. https://doi.org/10.1016/S0040-4039(99)00194-X
Dermenci, A., Whittaker, R.E., and Dong, G., Org. Lett., 2013, vol. 15, p. 2242. https://doi.org/10.1021/ol400815y
Rao, M.L.N., Islam, S.S., and Dasgupta, P., RSC Adv., 2015, vol. 5, p. 78090. https://doi.org/10.1039/C5RA15705F
Rao, M.L.N., Dasgupta, P., Ramakrishna, B.S., and Murty, V.N., Tetrahedron Lett., 2014, vol. 55, p. 3529. https://doi.org/10.1016/j.tetlet.2014.04.092
Andrade, C.B., Carvalho, D.B., Trefzger, O.S., Kassab, N.M., Guerrero, P.G.J., Barbosa, S.L., Shiguemoto, C.Y.K., and Baroni, A., Eur. J. Med. Chem., 2019, vol. 2019, p. 696. https://doi.org/10.1002/ejoc.201801242
Liu, Z.R. and Li, Z., Eur. J. Org. Chem., 2021, vol. 2021, p. 302. https://doi.org/10.1002/ejoc.202001324
Lin, Z., Yu, D., Sum, Y.N., and Zhang, Y., ChemSusChem., 2012, vol. 5, p. 625. https://doi.org/10.1002/cssc.201100649
Havashi, T., Kubo, A., and Ozawa, F., Pure Appl. Chem., 1992, vol. 64, p. 421. https://doi.org/10.1351/pac199264030421
Polynski, M.V., Sapova, M.D., and Ananikov, V.P., Chem. Sci., 2020, vol. 11, p. 13102. https://doi.org/10.1039/d0sc04752j
Hosseini, A., Pilevar, A., Hogan, E., Mogwitz, B., Schulze, A.S., and Schreiner, P.R., Org. Biomol. Chem., 2017, vol. 15, p. 6800. https://doi.org/10.1039/C7OB01334E
Lu, H. and Li, Z., Adv. Synth. Catal., 2019, vol. 361, p. 4474. https://doi.org/10.1002/adsc.201900733
Vilhelmsen, M.H., Jensen, J., Tortzen, C.G., and Nielsen, M.B., Eur. J. Org. Chem., 2013, vol. 3013, p. 701. https://doi.org/10.1002/ejoc.201201159
Seavill, P.W., Holt, K.B., and Wilden, J.D., Faraday Discuss., 2019, vol. 220, p. 269. https://doi.org/10.1039/c9fd00031c
Akhtar, R. and Zahoor, A.F., Synth. Commun., 2020, vol. 50, p. 3337. https://doi.org/10.1080/00397911.2020.1802757
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The author gratefully acknowledges financial support from the Hebei Chemical & Pharmaceutical College.
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Zhao, Z. Direct Synthesis of Unsymmetrical 1,3-Butadiynes from Calcium Carbide and Aryl Iodides. Russ J Org Chem 59, 1436–1444 (2023). https://doi.org/10.1134/S1070428023080183
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DOI: https://doi.org/10.1134/S1070428023080183