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Synthesis and Characterization of Ag(I) Complexes Derived from New N-Heterocyclic Carbenes
Corresponding Author(s) : Mohammed Mujbel Hasson
Asian Journal of Chemistry,
Vol. 31 No. 5 (2019): Vol 31 Issue 5
Abstract
Two new unsymmetrical imidazolium salts viz., [1-(4-ethylphenyl)-3-propyl-1H-imidazole-3-ium bromide] (3) and [1-(2,6-dimethylphenyl)-3-propyl-1H-imidazole-3-ium bromide] (4) have been synthesized via the reaction of propyl bromide with imidazole derivatives, [1-(4-ethylphenyl)-1H-imidazole] (1) and [1-(2,6-dimethylphenyl)-1H-imidazole] (2) in absence of solvent. Then two new N-heterocyclic carbene silver complexes (5 and 6) were prepared through the reaction of imidazoluim salts (3 and 4) as a source of N-heterocyclic carbene with Ag2O by in situ method. These complexes can be used in the future as a transfer agent for preparing other transitional metal carbine complexes (NHCs) via transmetallation method. The formation of these compounds was confirmed by spectral analysis.
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- A. Vellé, A. Cebollada, R. Macías, M. Iglesias, M. Gil-Moles and P.J. Sanz Miguel, ACS Omega, 2, 1392 (2017); https://doi.org/10.1021/acsomega.7b00138.
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References
A. Vellé, A. Cebollada, R. Macías, M. Iglesias, M. Gil-Moles and P.J. Sanz Miguel, ACS Omega, 2, 1392 (2017); https://doi.org/10.1021/acsomega.7b00138.
A. Kiyomori, J.-F. Marcoux and S.L. Buchwald, Tetrahedron Lett., 40, 2657 (1999); https://doi.org/10.1016/S0040-4039(99)00291-9.
W.A. Herrmann, L.J. Gooâen and M. Spiegler, Organomet.Chem., 547, 357 (1997); https://doi.org/10.1016/S0022-328X(97)00434-8.
F.E. Hahn, B. Heidrich, T. Lügger and T. Pape, Z. Naturforsch., 59, 1519 (2004); https://doi.org/10.1515/znb-2004-11-1223.
F. Ekkehardt Hahn, B. Heidrich, T. Pape, A. Hepp, M. Martin, E. Sola and L.A. Oro, Inorg. Chim. Acta, 359, 4840 (2006); https://doi.org/10.1016/j.ica.2006.07.010.
B. Cetinkaya, S. Demir. I. Ozdemir L. Toupet, D. Semeril, C. Bruneau and P.H. Dexnuef, Chem. Eur. J., 9, 2323 (2003); https://doi.org/10.1002/chem.200204533.
I. Özdemir, S. Demir, B. Çetinkaya, L. Toupet, R. Castarlenas, C. Fischmeister and P.H. Dixneuf, Eur. J. Inorg. Chem., 18, 2862 (2007); https://doi.org/10.1002/ejic.200601189.
A.A. Danopoulos, N. Tsoureas, J.A. Wright and M.E. Light, Organometallics, 23, 166 (2004); https://doi.org/10.1021/om0341911.
A.A.D. Tulloch, A.A. Danopoulos, S. Winston, S. Kleinhenz and G. Eastham, J. Chem. Soc., Dalton Trans., 4499 (2000); https://doi.org/10.1039/b007504n.
T. Weskamp, V.P.W. Böhm and W.A. Herrmann, J. Organomet. Chem., 600, 12 (2000); https://doi.org/10.1016/S0022-328X(00)00035-8.
N. Gonsior, F. Mohr and H. Ritter, Beilstein J. Org. Chem., 8, 390 (2012); https://doi.org/10.3762/bjoc.8.42.
V. Lavallo, Y. Canac, A. DeHope, B. Donnadieu and G. Bertrand, Angew. Chem., 117, 7402 (2005); https://doi.org/10.1002/ange.200502566.
R.H. Crabtree, J. Organomet. Chem., 690, 5451 (2005); https://doi.org/10.1016/j.jorganchem.2005.07.099.
I.J.B. Lin and C.S. Vasam, Can. J. Chem., 83, 812 (2005); https://doi.org/10.1139/v05-087.
K.J. Cavell and D.S. McGuinness, Coord. Chem. Rev., 248, 671 (2004); https://doi.org/10.1016/j.ccr.2004.02.006.
A.J. Arduengo III, R.L. Harlow and M. Kline, J. Am. Chem. Soc., 113, 361 (1991); https://doi.org/10.1021/ja00001a054.
J.C. Garrison and W.J. Youngs, Chem. Rev., 105, 3978 (2005); https://doi.org/10.1021/cr050004s.
I.J. Lin and C.S. Vasam, Comments Inorg. Chem., 25, 75 (2004); https://doi.org/10.1080/02603590490883652.
H.M.J. Wang and I.J.B. Lin, J. Chem. Organomet., 17, 972 (1998); https://doi.org/10.1021/om9709704.
M.Z. Ghdhayeb, R.A. Haque and S. Budagumpi, J. Organomet. Chem., 757, 42 (2014); https://doi.org/10.1016/j.jorganchem.2014.01.038.
H.-L. Su, L.M. Pérez, S.-J. Lee, J.H. Reibenspies, H.S. Bazzi and D.E. Bergbreiter, Organometallics, 31, 4063 (2012); https://doi.org/10.1021/om300340w.
M.K. Lee, H.M.J. Wang and I.J.B. Lin, J. Chem. Soc., Dalton Trans., 2852 (2002); https://doi.org/10.1039/b201957d.
S. Warsink, P. Hauwert, M.A. Siegler, A.L. Spek and C.J. Elsevier, J. Appl. Organomet. Chem., 23, 225 (2009); https://doi.org/10.1002/aoc.1501.
Y.A. Wanniarachchi, M.A. Khan and L.G.M. Slaughter, Organometallics, 23, 5881 (2004); https://doi.org/10.1021/om0493098.
A.J. Arduengo III, Preparation of 1,3-Disubstituted Imidazolium Salts, US Patent 5077414 (1991).
J. Liu, J. Chen, J. Zhao, Y. Zhao, L. Li and H. Zhang, Synthesis, 2661 (2003); https://doi.org/10.1055/s-2003-42444.
E.P. Çoban, R. Firinci, H. Biyik and M.E. Günay, Braz. J. Pharm. Sci., 53, e15075 (2017); https://doi.org/10.1590/s2175-97902017000115075.
F. Almalioti, J. MacDougall, S. Hughes, M.M. Hasson, R.L. Jenkins, B.D. Ward, G.J. Tizzard, S.J. Coles, D.W. Williams, S. Bamford, I.A. Fallis and A. Dervisi, Dalton Trans., 42, 12370 (2013); https://doi.org/10.1039/c3dt51400e.
A. Poethig and T. Strassner, Organometallics, 30, 6674 (2011); https://doi.org/10.1021/om200860y.
P. Newman, G.J. Clarkson and J.P. Rourke, J. Organomet. Chem., 692, 4962 (2007); https://doi.org/10.1016/j.jorganchem.2007.07.041.
B. Bildstein, M. Malaun, H. Kopacka, K. Wurst, M. Mitterbock, K. Ongania, G. Opromolla and P.J. Zanello, Organomet. Chem., 18, 4325 (1999); https://doi.org/10.1021/om990377h.