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Synthesis of Cationic Pd(II) Complexes with 5-Membered Ring Chelating Iminoylcarbene Ligand and Its Catalytic Activity on Norbornene Polymerization
Corresponding Author(s) : Tariqul Hasan
Asian Journal of Chemistry,
Vol. 31 No. 3 (2019): Vol 31 Issue 3
Abstract
Iminoyl N-heterocyclic carbine ligand with cationic allyl Pd(II) complex (3) was successfully synthesized by transmetallation of corresponding Ag complex with one equivalent of [Pd(allyl)(COD)]+SbF6–. A slightly distorted square planer structure of the Pd(II) complex 3 was confirmed by single crystal X-ray diffraction analysis. The Pd(II) complex 3 is stable in air and found to show moderate activity in the polymerization of norbornene without any activator. The polynorbornene produced with Pd(II) complex 3 was obtained to be stable up to 440 °C. The 1H and 13C NMR spectra of the polymer indicated addition polymerization of norbornene and the presence of the vinylene group at the end of polymer chain.
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References
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F. Glorius, N-Heterocyclic Carbenes in Transition Metal Catalysis, Springer: Berlin, Heidelberg (2007).
M.N. Hopkinson, C. Richter, M. Schedler and F. Glorius, Nature, 510, 485 (2014); https://doi.org/10.1038/nature13384.
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.M. Scott and S.P. Nolan, Eur. J. Inorg. Chem., 2005, 1815 (2005); https://doi.org/10.1002/ejic.200500030.
E. Peris and R.H. Crabtree, Coord. Chem. Rev., 248, 2239 (2004); https://doi.org/10.1016/j.ccr.2004.04.014.
W.A. Herrmann, Angew. Chem. Int. Ed., 41, 1290 (2002); https://doi.org/10.1002/1521-3773(20020415)41:8<1290::AIDANIE1290>3.0.CO;2-Y.
A.J. Arduengo Jr., Acc. Chem. Res., 32, 913 (1999); https://doi.org/10.1021/ar980126p.
S. Díez-González, N. Marion and S.P. Nolan, Chem. Rev., 109, 3612 (2009); https://doi.org/10.1021/cr900074m.
T.M. Trnka and R.H. Grubbs, Acc. Chem. Res., 34, 18 (2001); https://doi.org/10.1021/ar000114f.
H.M. Lee, D.C. Smith, Z.J. He, E.D. Stevens, C.S. Yi and S.P. Nolan, Organometallics, 20, 794 (2001); https://doi.org/10.1021/om000882a.
L. Yin and L. Liebscher, Chem. Rev., 107, 133 (2007); https://doi.org/10.1021/cr0505674.
G.C. Fortman and S.P. Nolan, Chem. Soc. Rev., 40, 5151 (2011); https://doi.org/10.1039/c1cs15088j.
M.G. Gardiner, W.A. Herrmann, C.P. Reisinger, J. Schwarz and M. Spiegler, J. Organomet. Chem., 572, 239 (1999); https://doi.org/10.1016/S0022-328X(98)00960-7.
X. Sauvage, Y. Borguet, A.F. Noels, L. Delaude and A. Demonceau, Adv. Synth. Catal., 349, 255 (2007); https://doi.org/10.1002/adsc.200600515.
V. Khlebnikov, A. Meduri, H. Mueller-Bunz, T. Montini, P. Fornasiero, E. Zangrando, B. Milani and M. Albrecht, Organometallics, 31, 976 (2012); https://doi.org/10.1021/om201027y.
V. Khlebnikov, A. Meduri, H. Mueller-Bunz, B. Milani and M. Albrecht, New J. Chem., 36, 1552 (2012); https://doi.org/10.1039/c2nj40287d.
D. McGuinness, Dalton Trans., 6915 (2009); https://doi.org/10.1039/b906479f.
S. Mecking, Angew. Chem. Int. Ed., 40, 534 (2001); https://doi.org/10.1002/1521-3773(20010202)40:3<534::AIDANIE534>3.0.CO;2-C.
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S.D. Ittel, L.K. Johnson and M. Brookhart, Chem. Rev., 100, 1169 (2000); https://doi.org/10.1021/cr9804644.
H. Gao, H. Hu, F. Zhu and Q. Wu, Chem. Commun., 48, 3312 (2012); https://doi.org/10.1039/c2cc17154f.
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S.P. Nolan, N-Heterocyclic Carbenes in Synthesis, Wiley-VCH: Weinheim, Germany (2006).
S.T. Nguyen and T.M. Trnka, ed.: R.H. Grubbs, Handbook of Metathesis, Wiley-VCH: Weinheim, Germany, vol. 1 (2003).
B.F. Straub, Angew. Chem. Int. Ed., 44, 5974 (2005); https://doi.org/10.1002/anie.200501114.
M.R. Buchmeiser, Chem. Rev., 100, 1565 (2000); https://doi.org/10.1021/cr990248a.
C.W. Bielawski and R.H. Grubbs, Angew. Chem. Int. Ed., 39, 2903 (2000); https://doi.org/10.1002/1521-3773(20000818)39:16<2903::AIDANIE2903>3.0.CO;2-Q.
N.D. Clement and K.J. Cavell, Angew. Chem. Int. Ed., 43, 3845 (2004); https://doi.org/10.1002/anie.200454166.
W. Keim, Angew. Chem. Int. Ed. Engl., 29, 235 (1990); https://doi.org/10.1002/anie.199002351.
E. Drent, P. Arnoldy and P.H.M. Budzelaar, J. Organomet. Chem., 475, 57 (1994); https://doi.org/10.1016/0022-328X(94)84007-5.
J.C.C. Chen and I.J.B. Lin, Organometallics, 19, 5113 (2000); https://doi.org/10.1021/om000557n.
D.S. McGuinness, V.C. Gibson and J.W. Steed, Organometallics, 23, 6288 (2004); https://doi.org/10.1021/om049246t.
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W. Li, H. Sun, M. Chen, Z. Wang, D. Hu, Q. Shen and Y. Zhang, Organometallics, 24, 5925 (2005); https://doi.org/10.1021/om050612y.
J. Cámpora, L. Ortiz de la Tabla, P. Palma, E. Álvarez, F. Lahoz and K. Mereiter, Organometallics, 25, 3314 (2006); https://doi.org/10.1021/om060439l.
B.L. Goodall, T.C. Kirk and L.H. McIntosh III, Preparation of Linear Ethylene-Acrylate Copolymers with Palladium Catalysts and Free Radical Scavengers, US Patent 7524912B2 (2009).
I.G. Jung, J.H. Seo, Y.K. Chung, D.M. Shin, S.-H. Chun and S.U. Son, J. Polym. Sci. A Polym. Chem., 45, 3042 (2007); https://doi.org/10.1002/pola.22060.
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Y. Kong, H. Ren, S. Xu, H. Song, B. Liu and B. Wang, Organometallics, 28, 5934 (2009); https://doi.org/10.1021/om900625r.
J. Deng, H. Gao, F. Zhu and Q. Wu, Organometallics, 32, 4507 (2013); https://doi.org/10.1021/om400268y.
D.A. White, J.R. Doyle and H. Lewis, Inorg. Synth., 13, 55 (1972).
M. Frøseth, K.A. Netland, C. Rømming and M. Tilset, J. Organomet. Chem., 690, 6125 (2005); https://doi.org/10.1016/j.jorganchem.2005.08.008.
T. Hasan, K. Nishii, T. Shiono and T. Ikeda, Macromolecules, 35, 8933 (2002); https://doi.org/10.1021/ma025586j.
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