Catalytic activity assessment of [RuCl2 (p-cymene) (PTA)] in the synthesis of enol esters
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- 作者：Eric Musengimana ; Claver Fatakanwa
- 关键词：[RuCl2 (p ; cymene) (PTA)] ; 1 ; Hexyne ; Carboxylic acids ; Enol esters ; Catalyst loading ; Microwave chemistry
- 刊名：Journal of the Iranian Chemical Society
- 出版年：2016
- 出版时间：February 2016
- 年：2016
- 卷：13
- 期：2
- 页码：253-259
- 全文大小：819 KB
- 参考文献：1.L. Perrin, E. Clot, O. Eisenstein, J. Loch, R.H. Crabtree, Inorg. Chem. 40, 5806 (2001)CrossRef
2.D.J.M. Snelders, G. van Koten, R.J.M. Klein, Gebbink. Chem. Eur. J. 17, 42 (2011)CrossRef
3.C.S. Allardyce, P. J. Dyson, D. J. Ellis, S. L. Heath, Chem. Commun. 1396 (2001)
4.A.D. Phillips, L. Gonsalvi, A. Romerosa, F. Vizza, M. Peruzzini, Coord. Chem. Rev. 248, 955 (2004)CrossRef
5.C.S. Allardyce, P.J. Dyson, D.J. Ellis, P.A. Salter, R. Scopelliti, J. Organomet. Chem. 668, 35 (2003)CrossRef
6.W.H. Ang, Chimia 61, 140 (2007)CrossRef
7.A. Bergamo, C. Gaiddon, J.H.M. Schellens, J.H. Beijnen, G. Sava, J. Inorg. Biochem. 106, 90 (2012)CrossRef
8.J. Bravo, S. Bolano, L. Gonsalvi, M. Peruzzini, Coord. Chem. Rev. 254, 555 (2010)CrossRef
9.W.H. Ang, A. Casini, G. Sava, P.J. Dyson, J. Organomet. Chem. 696, 989 (2011)CrossRef
10.A.E. Diaz-Alvarez, P. Crochet, V. Cadierno, Catal. Commun. 13, 91 (2011)CrossRef
11.V. Cadierno, J. Diez, J. François, J. Gimeno, Chem. Eur. J. 16, 9808 (2010)CrossRef
12.S. Tat Tan, W. Y. Fan, Eur. J. Inorg. Chem. 4631 (2010)
13.H. Nakagawa, Y. Okimoto, S. Sakagushi, Y. Ishii, Tetrahedron Lett. 44, 103 (2003)CrossRef
14.W. Kitching, Z. Rapport, S. Winstein, W.G. Young, J. Am. Chem. Soc. 88, 2054 (1966)CrossRef
15.H. Kawano, Y. Masaki, T. Matsunaga, K. Hiraki, M. Onishi, T. Tsubomura, J. Organomet. Chem. 601, 69 (2000)CrossRef
16.P.F. Hudrlik, A.M. Hudrlik, J. Org. Chem. 38, 4254 (1973)CrossRef
17.E. Rothman, S. Hecht, P. Pfeffer, L. Silbert, J. Org. Chem. 37, 3551 (1972)CrossRef
18.X. Lu, G. Zhu, S. Ma, Tetrahedron Lett. 33, 7205 (1992)CrossRef
19.C. Bianchini, A. Meli, M. Peruzzini, F. Zanobini, C. Bruneau, P. Dixneuf, Organometallics 9, 1155 (1990)CrossRef
20.K. Melis, T. Opstal, F. Verpoort, Eur. J. Org. Chem. 3779 (2002)
21.Q. Willem, F. Nicks, X. Sauvage, L. Delaude, A. Demonceau, J. Organomet. Chem. 694, 4049 (2009)CrossRef
22.F. Nicks, R. Aznar, D. Sainz, G. Muller, A. Demonceau, Eur. J. Org. Chem. 5020 (2009)
23.F. Nicks, L. Libert, L. Delaude, A. Demonceau, Aust. J. Chem. 62, 227 (2009)CrossRef
24.V. Cadierno, J. Diez, J. Francos, J. Gimeno, Organometallics 30, 852 (2011)CrossRef
25.S. Warratz, C. Kornhaaß, A. Cajaraville, B. Niepötter, D. Stalke, L. Ackermann, Angew. Chem. Int. Ed. 54, 5513 (2015)CrossRef
26.M. Rotem, Y. Shvo, J. Organomet. Chem. 448, 189 (1993)CrossRef
27.H. Doucet, B. Martin-Vaca, C. Bruneau, P.H. Dixneuf, J. Org. Chem. 60, 7247 (1995)CrossRef
28.C. Bruneau, M. Neveux, Z. Kabouche, C. Ruppin, P. H. Dixneuf, Synlett, 755 (1991)
29.S. Costin, N.P. Rath, E.B. Bauer, Adv. Synth. Cat. 350, 2414 (2008)CrossRef
30.M. Jiménez-Tenorio, M. C. Puerta, P. Valerga, F. J.Moreno-Dorado, F. M. Guerra, G. M. Massanet, Chem. Commun. 2324 (2001)
31.C. Ruppin, P.H. Dixneuf, Tetrahedron Lett. 27, 6323 (1986)CrossRef
32.K. Philippot, D. Devanne, P. H. Dixneuf, J. Chem. Soc. Chem. Commun. 1199 (1990)
33.M. Neveux, C. Bruneau, P.H. Dixneuf, J. Chem. Soc., Perkin Trans. 1, 1197 (1991)CrossRef
34.Y. Kita, H. Maeda, K. Omori, T. Okuno, Y. Tamura, J. Chem. Soc. Perkin Trans. 1, 2999 (1993)CrossRef
35.C. Bruneau, P. H. Dixneuf, Chem. Commun. 507 (1997)
36.H. Doucet, N. Derrien, Z. Kabouche, C. Bruneau, P.H. Dixneuf, J. Organomet. Chem. 551, 151 (1998)CrossRef
37.N.E. Leadbeater, K.A. Scott, L.J. Scott, J. Org. Chem. 65, 3231 (2000)CrossRef
38.P. Le Gendre, V. Comte, A. Michelot, C. Moïse, Inorg. Chim. Acta. 350, 289 (2003)CrossRef
39.L. J. Goossen, J. Paetzold, D. Koley, Chem. Commun. 706 (2003)
40.N.P. Hiett, J.M. Lynam, C.E. Welby, A.C. Whitwood, J. Org. Chem. 696, 378 (2001)CrossRef
41.H. J. Günther, E. Guntrum, V. Jäger, Liebigs Ann. Chem. 15 (1984) - 作者单位：Eric Musengimana (1)
Claver Fatakanwa (1)
1. Department of Chemistry, School of Sciences, University of Rwanda, PO Box 117, Butare, Rwanda - 刊物主题：Analytical Chemistry; Inorganic Chemistry; Physical Chemistry; Biochemistry, general; Organic Chemistry;
- 出版者：Springer Berlin Heidelberg
- ISSN：1735-2428
文摘
The addition of carboxylic acids onto 1-hexyne was catalyzed by [RuCl2 (p-cymene) (PTA)] complex to give enol esters. Accordingly, the Markovnikov addition-type product was selectively obtained. The microwave-assisted reactions at 160 °C confirmed the influence of the temperature, where quantitative to excellent yields were obtained in 30 min. The catalyst loading test proved that [RuCl2 (p-cymene) (PTA)] complex can be efficiently used with a 1/1500 ratio to carboxylic acid providing the TON value of 1500. Keywords [RuCl2 (p-cymene) (PTA)] 1-Hexyne Carboxylic acids Enol esters Catalyst loading Microwave chemistry