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Letters in Organic Chemistry

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

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Letter Article

Application of Amine-based Ru Compounds in the Olefin Metathesis of Methyl Eugenol: A Comparison with Grubbs Catalysts

Author(s): Denise A. Sousa, Paulo S. Meneses, Patrik D.S. Gois, Eliada A. Silva, Valdemiro P.C. Junior, Benedito S. Lima-Neto and José L. Silva Sá*

Volume 17, Issue 8, 2020

Page: [596 - 602] Pages: 7

DOI: 10.2174/1570178617666191127102552

Price: $65

Abstract

Methyl eugenol olefin metathesis was conducted with non-carbene Ru-complexes ([RuCl2(PPh3)2amine]) in the absence and presence of SnCl2 or CuCl2 as additives and their catalytic activities were compared with that of a commercial Grubbs catalyst 2nd Generation (G2).

Keywords: Olefin metathesis, Methyl-eugenol, SnCl2, CuCl2, ruthenium, additives.

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[1]
Grubbs, R.H. Tetrahedron, 2004, 5, 7117-7140.
[http://dx.doi.org/10.1016/j.tet.2004.05.124]
[2]
O’Leary, D.J.; O’Neil, G.W. Cross‐Metathesis, 2015, 2, 171-294.
[3]
Lionel, D.; Alfred, F. Kirk-Ohtmer, 2005, 29, 920-958.
[4]
Astruc, D. New J. Chem., 2005, 29, 42-56.
[http://dx.doi.org/10.1039/b412198h]
[5]
Trnka, T.M.; Grubbs, R.H. Acc. Chem. Res., 2001, 34(1), 18-29.
[http://dx.doi.org/10.1021/ar000114f] [PMID: 11170353]
[6]
Al-Ayed, A.S.; Hamdi, N.; Peruzzini, M. Asian J. Chem., 2016, 28(5), 960-964.
[http://dx.doi.org/10.14233/ajchem.2016.19554]
[7]
Yoshikai, K. Green Chem., 2011, 13, 1448-1452.
[8]
Fujita, H.; Yamashita, M. Chem. Soc. Jpn., 1973, 46, 3553-3554.
[http://dx.doi.org/10.1246/bcsj.46.3553]
[9]
Alexander, Kathryn. J. Organomet. Chem., 2016, 49, 74-80.
[http://dx.doi.org/10.1016/j.jorganchem.2015.09.018]
[10]
Collins, S.K. Handbook of Metathesis; , 2015, pp. 343-377.
[11]
Hong, S.H. JACS, 2005, 127, 17160-17161.
[http://dx.doi.org/10.1021/ja052939w]
[12]
Bilel, H.; Hamdi, N.; Zagrouba, F. RSC Advances, 2012, 2, 9584-9589.
[http://dx.doi.org/10.1039/c2ra21638h]
[13]
Schulz, M.D.; Atkinson, M.B.; Elsey, R.J.; Thuo, M.M. Chem, 2014, 39, 763-767.
[14]
Meyer, W.H.; McConnell, A.E.; Forman, G.S.; Dwyer, C.L.; Kirk, M.M.; Ngidi, E.L.; Slawin, A.M. Inorg. Chim. Acta, 2006, 359, 2910-2917.
[http://dx.doi.org/10.1016/j.ica.2005.12.032]
[15]
Hong, S.H.; Wenzel, A.G.; Salguero, T.T.; Day, M.W.; Grubbs, R.H. JACS, 2007, 129, 7961-7968.
[http://dx.doi.org/10.1021/ja0713577]
[16]
Cesar, V.; Zhang, Y.; Konik, W.; Zieliski, A.; Rajkiewicz, A. A.; Ruamps, M.; Bastin, S.; Lugan, N.; Lavigne, G.; Grela, K. Che A Eur J., 2017, 23, 1950-1955.
[17]
Johns, A.M.; Ahmed, T.S. Org. Lett., 2016, 18, 772-775.
[http://dx.doi.org/10.1021/acs.orglett.6b00031] [PMID: 26840878]
[18]
Martin, D.; Marx, V.M.; Grubbs, R.H.; Bertrand, G. Adv. Synth. Catal., 2016, 358(6), 965-969.
[http://dx.doi.org/10.1002/adsc.201501140] [PMID: 27594819]
[19]
Nguyen, S.T.; Johnson, L.K.; Grubbs, R.H.; Ziller, J.W. J. Am. Chem. Soc., 1992, 114, 3974-3975.
[http://dx.doi.org/10.1021/ja00036a053]
[20]
Carvalho, V.P., Jr Quim. Nova, 2012, 35, 791-801.
[21]
Fonseca, L.R.; Nascimento, E.S.P.; Sá, J.L.S.; Lima-Neto, B.S. New J. Chem., 2015, 39(5), 4063-4069.
[http://dx.doi.org/10.1039/C5NJ00321K]
[22]
Matos, J.M.E.; Lima-Neto, B.S. J. Mol. Catal. Chem., 2004, 222, 81-84.
[http://dx.doi.org/10.1016/j.molcata.2004.08.021]
[23]
Sá, J.L.S.; Vieira, L.H.; Nascimento, E.S.P.; Lima-Neto, B.S. Appl. Catal., 2010, 374, 194-200.
[24]
Sá, J.L.S.; Nascimento, E.S.P.; Fonseca, L.R.; Lima-Neto, B.S. J. Appl. Polym. Sci., 2013, 127, 3578-3585.
[http://dx.doi.org/10.1002/app.37741]
[25]
Miao, X.; Blokhin, A.; Pasynskii, A.; Nefedov, S.; Osipov, S.N.; Roisnel, T. Organometallics, 2010, 29(21), 5257-5262.
[http://dx.doi.org/10.1021/om100372b]
[26]
Blackwell, H.E.; O’Leary, D.J.; Chatterjee, A.K.; Washenfelder, R.A.; Bussmann, D.A.; Grubbs, R.H. JACS, 2000, 122, 58-71.
[http://dx.doi.org/10.1021/ja993063u]
[27]
Santos, D. ChemSusChem, 2017, 10, 1832-1837.
[28]
Bailey, G.A.; Lummiss, J.A.; Foscato, M.; Occhipinti, G.; McDonald, R.; Jensen, V.R.; Fogg, D.E. JACS, 2017, 139, 16446-16449.
[http://dx.doi.org/10.1021/jacs.7b08578]
[29]
Engel, J.; Smit, W.; Foscato, M.; Occhipinti, G.; Törnroos, K.W.; Jensen, V.R. JACS, 2017, 139, 16609-16619.
[http://dx.doi.org/10.1021/jacs.7b07694]
[30]
Dinger, M.B.; Mol, J.C. Organometallics, 2003, 22, 1089-1095.
[http://dx.doi.org/10.1021/om0208218]
[31]
Grandner, J.M.; Shao, H.; Grubbs, R.H.; Liu, P.; Houk, K.N. JOC, 2017, 82, 10595-10600.
[http://dx.doi.org/10.1021/acs.joc.7b02129]
[32]
Lehman, S.E., Jr; Schwendeman, J.E.; O’Donnell, P.M.; Wagener, K.B. Inorg. Chim. Acta, 2003, 345, 190-198.
[http://dx.doi.org/10.1016/S0020-1693(02)01307-5]
[33]
Fokou, P.A.; Meier, M.A.R. Macromol. Rapid Commun., 2010, 31, 368-373.
[http://dx.doi.org/10.1002/marc.200900678]
[34]
Schmidt, B. Eur. J. Org. Chem., 2004, 2004, 1865-1880.
[http://dx.doi.org/10.1002/ejoc.200300714]
[35]
Nelson, D.J.; Percy, J.M. Dalton Trans., 2014, 43(12), 4674-4679.
[http://dx.doi.org/10.1039/C4DT00007B] [PMID: 24488325]

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