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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Microwave-assisted, Copper-free Sonogashira Coupling Between Aryl Halides and Terminal Alkynes Using Recyclable Ionic Liquid and Catalyst

Author(s): Dau Xuan Duc* and Nguyen Van Quoc

Volume 19, Issue 1, 2022

Published on: 20 August, 2021

Page: [28 - 33] Pages: 6

DOI: 10.2174/1570178618666210820101129

Price: $65

Abstract

An efficient method for the Sonogashira coupling reaction between aryl halides and terminal alkynes has been developed. The reaction was performed in ionic liquid 1-butyl-3- methylimidazolium tetrafluoroborate ([Bmim][BF4]) under microwave irradiation. High yields of products were obtained in a very short reaction time. Moreover, the medium and catalyst could be recovered and reused three times without considerable decrease in reaction yields.

Keywords: Coupling reaction, terminal alkynes, ionic liquid, microwave, trimethylsillylacetylene, iodide.

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[1]
Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett., 1975, 16, 4467-4470.
[http://dx.doi.org/10.1016/S0040-4039(00)91094-3]
[2]
(a) Paterson, I.; Davies, R.D.M.; Marquez, R. Angew. Chem. Int. Ed., 2001, 40, 603-607.
[http://dx.doi.org/10.1002/1521-3773(20010202)40:3<603::AIDANIE603>3.0.CO;2-O]
(b) Toyota, M.; Komori, C.; Ihara, M. J. Org. Chem., 2000, 65(21), 7110-7113.
[http://dx.doi.org/10.1021/jo000816i] [PMID: 11031036]
(c) Yoshimura, F.; Kawata, S.; Hirama, M. Tetrahedron Lett., 1999, 40, 8281-8285.
[http://dx.doi.org/10.1016/S0040-4039(99)01744-X]
(d) Miller, M.W.; Johnson, C.R. J. Org. Chem., 1997, 62, 1582-1583.
[http://dx.doi.org/10.1021/jo962295y]
(e) Sakai, A.; Aoyama, T.; Shioiri, T. Tetrahedron Lett., 1999, 40, 4211-4214.
[http://dx.doi.org/10.1016/S0040-4039(99)00714-5]
(f) Graham, A.E.; McKerrecher, D.; Davies, D.H.; Taylor, R.J.K. Tetrahedron Lett., 1996, 37, 7445-7448.
[http://dx.doi.org/10.1016/0040-4039(96)01607-3]
(g) Bunz, U.H.F. Chem. Rev., 2000, 100(4), 1605-1644.
[http://dx.doi.org/10.1021/cr990257j] [PMID: 11749277]
(h) Tour, J.M. Acc. Chem. Res., 2000, 33(11), 791-804.
[http://dx.doi.org/10.1021/ar0000612] [PMID: 11087316]
(i)Chinchilla, R.; Nájera, C. Chem. Rev., 2007, 107(3), 874-922.
[http://dx.doi.org/10.1021/cr050992x] [PMID: 17305399]
(j)Chinchilla, R.; Nájera, C. Chem. Soc. Rev., 2011, 40(10), 5084-5121.
[http://dx.doi.org/10.1039/c1cs15071e] [PMID: 21655588]
[3]
(a) Brun, V.; Legraverend, M. Tetrahedron Lett., 2001, 42, 8169-8171.
[http://dx.doi.org/10.1016/S0040-4039(01)01753-1]
(b) Fairlamb, I.J.S.; Bäuerlein, P.S.; Marrison, L.R.; Dickinson, J.M. Chem. Commun. (Camb.), 2003, (5), 632-633.
[http://dx.doi.org/10.1039/b212430k] [PMID: 12669860]
(c) Hopkins, C.R.; Collar, N. Tetrahedron Lett., 2004, 43, 8087-8090.
[http://dx.doi.org/10.1016/j.tetlet.2004.08.155]
(d) Liang, B.; Dai, M.; Chen, J.; Yang, Z. J. Org. Chem, 2005, 70(1), 391-393.
[http://dx.doi.org/10.1021/jo048599z] [PMID: 15624959]
(e) Schilz, M.; Plenio, H. J. Org. Chem., 2012, 77(6), 2798-2807.
[http://dx.doi.org/10.1021/jo202644g] [PMID: 22390837]
[4]
(a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett., 2002, 4(10), 1691-1694.
[http://dx.doi.org/10.1021/ol0257732] [PMID: 12000275]
(b) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem., 2001, 624, 114-123.
[http://dx.doi.org/10.1016/S0022-328X(00)00909-8]
(c) Thorand, S.; Krause, N. J. Org. Chem., 1998, 63, 8551-8553.
[http://dx.doi.org/10.1021/jo9808021]
[5]
(a) Dai, W-M.; Guo, D-S.; Sun, L-P. Tetrahedron Lett., 2001, 42, 5275-5278.
[http://dx.doi.org/10.1016/S0040-4039(01)00965-0]
(b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett, 1999, 549- 550.
[http://dx.doi.org/10.1055/s-1999-2684]
(c) Crisp, G.T.; Turner, P.D.; Stephens, K.A. J. Organomet. Chem., 1998, 570, 219-224.
[http://dx.doi.org/10.1016/S0022-328X(98)00765-7]
[6]
(a) Chow, H-F.; Wan, C-W.; Low, K-H.; Yeung, Y-Y. J. Org. Chem., 2001, 66(5), 1910-1913.
[http://dx.doi.org/10.1021/jo001538q] [PMID: 11262146]
(b) Tzschucke, C.C.; Markert, C.; Glatz, H.; Bannwarth, W. Angew. Chem. Int. Ed., 2002, 41, 4500-4503.
[http://dx.doi.org/10.1002/1521-3773(20021202)41:23<4500::AIDANIE4500> 3.0.CO;2-N]
(c) Kabalka, G.W.; Wang, L.; Namboodiri, V.; Pagni, R.M. Tetrahedron Lett., 2000, 41, 5151-5154.
[http://dx.doi.org/10.1016/S0040-4039(00)00774-7]
[7]
Luque, R.; Macquarrie, D.J. Org. Biomol. Chem., 2009, 7(8), 1627-1632.
[http://dx.doi.org/10.1039/b821134p] [PMID: 19343249]
[8]
(a) Alonso, D.A.; Najera, C.; Pacheco, M.C. Tetrahedron Lett., 2002, 43, 9365-9368.
[http://dx.doi.org/10.1016/S0040-4039(02)02335-3]
(b) Fu, X.; Zhang, S.; Yin, J.; Schumacher, D.P. Tetrahedron Lett., 2002, 43, 6673-6676.
[http://dx.doi.org/10.1016/S0040-4039(02)01447-8]
(c) Wu, M-J.; Wei, L-M.; Lin, C-F.; Leou, S-P.; Wei, L-L. Tetrahedron, 2001, 57, 7839-7844.
[http://dx.doi.org/10.1016/S0040-4020(01)00758-X]
(d) Uozumi, Y.; Kobayashi, Y. Heterocycles, 2003, 59, 71-74.
[http://dx.doi.org/10.3987/COM-02-S21]
(e) Volker, P.W.B.; Herrmann, W.A. Eur. J. Org. Chem., 2000, 22, 3679-3681.
(f) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett., 1993, 34, 6403-6406.
[http://dx.doi.org/10.1016/0040-4039(93)85056-3]
[9]
(a) Kmentova, I.; Gotov, B.; Gajda, V. Monatsh. Chem., 2003, 134, 545-549.
(b) Hierso, J-C.; Picquet, M.; Cattey, H.; Meunier, P. Synlett, 2006, 18, 3005-3008.
[http://dx.doi.org/10.1055/s-2006-951503]
(c) Li, Y.; Zhang, J.; Wang, W.; Miao, Q.; She, X.; Pan, X. J. Org. Chem., 2005, 70(8), 3285-3287.
[http://dx.doi.org/10.1021/jo047836v] [PMID: 15822996]
(d) Park, S.B.; Alper, H. Chem. Commun. (Camb.), 2004, (11), 1306-1307.
[http://dx.doi.org/10.1039/b402477j] [PMID: 15154049]
[10]
(a) Erdélyi, M.; Gogoll, A. J. Org. Chem., 2001, 66(12), 4165-4169.
[http://dx.doi.org/10.1021/jo0057250] [PMID: 11397149]
(b) Leadbeater, N.E.; Marco, M.; Tominack, B.J. Org. Lett., 2003, 5(21), 3919-3922.
[http://dx.doi.org/10.1021/ol035485l] [PMID: 14535743]
(c) Chen, G.; Zhu, X.; Cai, J.; Wan, Y. Synth. Commun., 2007, 37, 1355-1361.
[http://dx.doi.org/10.1080/00397910701227416]
(d) Colacino, E.; Daïch, L.; Martinez, J.; Lamaty, F. Synlett, 2007, 8, 1279-1283.
[11]
Uhl, W.; Kovert, D.; Zemke, S.; Hepp, A. Organometallics, 2011, 30, 4736-4741.
[http://dx.doi.org/10.1021/om200573g]
[12]
Fabrizi, G.; Goggiamani, A.; Sferrazza, A.; Cacchi, S. Angew. Chem. Int. Ed., 2010, 49, 4067-4070.
[http://dx.doi.org/10.1002/anie.201000472]
[13]
Ladouceur, S.; Soliman, A.M.; Zysman-Colman, E. Synthesis, 2011, 22, 3604-3611.
[14]
Xu, C.; Du, W.; Zeng, Y.; Dai, B.; Guo, H. Org. Lett., 2014, 16(3), 948-951.
[http://dx.doi.org/10.1021/ol403684a] [PMID: 24467594]
[15]
Spencer, J.; Rathnam, R.P.; Patel, H.; Anjum, N. Tetrahedron, 2008, 64, 10195-10200.
[http://dx.doi.org/10.1016/j.tet.2008.08.036]
[16]
Sakai, N.; Annaka, K.; Fujita, A.; Sato, A.; Konakahara, T. J. Org. Chem., 2008, 73(11), 4160-4165.
[http://dx.doi.org/10.1021/jo800464u] [PMID: 18442294]
[17]
Koumbis, A.E.; Kyzas, C.M.; Savva, A.; Varvoglis, A. Molecules, 2005, 10(10), 1340-1350.
[http://dx.doi.org/10.3390/10101340] [PMID: 18007528]
[18]
Niamnont, N.; Siripornnoppakhun, W.; Rashatasakhon, P.; Sukwattanasinitt, M. Org. Lett., 2009, 11(13), 2768-2771.
[http://dx.doi.org/10.1021/ol900929g] [PMID: 19496606]
[19]
Fortin, S.; Moreau, E.; Patenaude, A.; Desjardins, M.; Lacroix, J.; Rousseau, J.L.C. Bioorg. Med. Chem., 2007, 15, 1430-1438.
[http://dx.doi.org/10.1016/j.bmc.2006.11.005] [PMID: 17118664]

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