Nickel and palladium complexes of enolatefunctionalised N-heterocyclic carbenes

• Authors: Saravanakumar Shanmuganathan , Olaf Kühl , Peter Jones , Joachim Heinicke
• Languages of publication: EN

Abstracts

EN

The reaction of chloroethyltrimethylsilylether with 1-methylimidazole furnishes an ionic liquid that undergoes methanolysis to crystalline 2-hydroxyethylimidazolium chloride (crystal structure presented). Conversion to defined hydroxyethylimidazol-2-ylidene nickel complexes failed, but was accomplished with 1-methyl-3-acetophenyl-imidazolium bromide. The bis(NHC⋂O−) nickel(II) chelate is formed, rather than a methallylnickel monochelate, but with nickelocene a monochelate NiCp complex was detected. The bulky 1-(2,6-diisopropylphenyl)-3-(2’-phenyl-enolato)-imidazol-2-ylidene allylpalladium chloride was obtained in pure form. Attempts to generate catalysts for ethylene oligomerization by in situ techniques have failed so far whereas P⋂O− ligands, comparable by the P-C diagonal relationship, provide active catalysts. [...]

Keywords

EN

Functionalized imidazolium salt; N-heterocyclic carbenes; Nickel; Palladium complexes

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 5
• Pages: 992-998

Dates

published

1 - 10 - 2010

online

5 - 9 - 2010

Contributors

author

Saravanakumar Shanmuganathan

• Institute of Biochemistry - Inorganic Chemistry, Ernst-Moritz-Arndt-University Greifswald, D-17489, Greifswald, Germany

author

Olaf Kühl

• Institute of Biochemistry - Inorganic Chemistry, Ernst-Moritz-Arndt-University Greifswald, D-17489, Greifswald, Germany

author

Peter Jones

• Institute of Inorganic and Analytical Chemistry, Technical University Braunschweig, D-38106, Braunschweig, Germany

author

Joachim Heinicke

• Institute of Biochemistry - Inorganic Chemistry, Ernst-Moritz-Arndt-University Greifswald, D-17489, Greifswald, Germany

References

• [1] C.S. Slone, D.A. Weinberger, C.A. Mirkin, Progress Inorg. Chem. 48, 233 (1999) http://dx.doi.org/10.1002/9780470166499.ch3[Crossref]
• [2] P. Braunstein, F. Naud, Angew. Chem. Int. Ed. 40, 680 (2001) http://dx.doi.org/10.1002/1521-3773(20010216)40:4<680::AID-ANIE6800>3.0.CO;2-0[Crossref]
• [3] W. Keim, Angew. Chem. Int. Ed. 29, 235 (1990) http://dx.doi.org/10.1002/anie.199002351[Crossref]
• [4] P. Kuhn, D. Semeril, D. Matt, M.J. Chetcuti, P. Lutz, Dalton Trans. 515 (2007)
• [5] A. Kermagoret, P. Braunstein, Dalton Trans. 822 (2008)
• [6] J. Heinicke, N. Peulecke, M. Kohler, M. He, W. Keim, J. Organomet. Chem. 690, 2449 (2005) http://dx.doi.org/10.1016/j.jorganchem.2004.10.012[Crossref]
• [7] A. Bader, E. Lindner, Coord. Chem. Rev. 108, 27 (1991) http://dx.doi.org/10.1016/0010-8545(91)80013-4[Crossref]
• [8] K. Nozaki, N. Sato, H. Takaya, J. Am. Chem. Soc. 117, 9911 (1995) http://dx.doi.org/10.1021/ja00144a018[Crossref]
• [9] W.A. Herrmann, C. Kocher, Angew. Chem. Int. Ed. 36, 2163 (1997)
• [10] A.J. Arduengo III, Acc. Chem. Res. 32, 913 (1999) http://dx.doi.org/10.1021/ar980126p[Crossref]
• [11] D. Bourissou, O. Guerret, F.P. Gabbai, G. Bertrand, Chem. Rev. 100, 39 (2000) http://dx.doi.org/10.1021/cr940472u[Crossref]
• [12] F.E. Hahn, M. Jahnke, Angew. Chem. Int. Ed. 47, 3122 (2008) http://dx.doi.org/10.1002/anie.200703883[Crossref]
• [13] K.B. Dillon, F. Mathey, J.F. Nixon, Phosphorus: The Carbon Copy - From Organophosphorus to Phospha-Organic Chemistry (Wiley, Chichester, 1998)
• [14] R.H. Crabtree, J. Organomet. Chem. 690, 5451 (2005) http://dx.doi.org/10.1016/j.jorganchem.2005.07.099[Crossref]
• [15] O. Kuhl, Chem. Soc. Rev. 36, 592 (2007) http://dx.doi.org/10.1039/b603765h[Crossref]
• [16] S.T. Liddle, I.S. Edworthy, P.L. Arnold, Chem. Soc. Rev. 36, 1732 (2007) http://dx.doi.org/10.1039/b611548a[Crossref]
• [17] A.T. Normand, K.J. Cavell, Eur. J. Inorg. Chem. 2781 (2008)
• [18] O. Kuhl, Functionalised N-Heterocyclic Carbene Complexes (Wiley, Chichester, 2010) http://dx.doi.org/10.1002/9780470685839[Crossref]
• [19] P.L. Arnold, I.J. Casely, Chem. Rev. 109, 3599 (2009) http://dx.doi.org/10.1021/cr8005203[Crossref]
• [20] C.-Y. Guo, N. Peulecke, M.K. Kindermann, J.W. Heinicke, J. Polym. Sci. A, Chem. Polym. 47, 258 (2009) http://dx.doi.org/10.1002/pola.23150[Crossref]
• [21] D.G. Yakhvarov, K.R. Basvani, M.K. Kindermann, A.B. Dobrynin, I.A. Litvinov, O.G. Sinyashin, P.G. Jones, J. Heinicke, Eur. J. Inorg. Chem. 1234 (2009)
• [22] S. Saravanakumar, A.I. Oprea, M.K. Kindermann, P.G. Jones, J. Heinicke, Chem. Eur. J. 12, 3143 (2006) http://dx.doi.org/10.1002/chem.200501183[Crossref]
• [23] S. Saravanakumar, M.K. Kindermann, J. Heinicke, M. Köckerling, Chem. Commun. 640 (2006) [Crossref]
• [24] F. Ullah, G. Bajor, T. Veszprémi, P.G. Jones, J. Heinicke, Angew. Chem. Int. Ed. 46, 2697 (2007) http://dx.doi.org/10.1002/anie.200604516[Crossref]
• [25] O. Kühl, S. Saravanakumar, F. Ullah, M.K. Kindermann, P.G. Jones, M. Köckerling, J. Heinicke, Polyhedron 27, 2825 (2008) http://dx.doi.org/10.1016/j.poly.2008.06.006[Crossref]
• [26] O. Kühl, G.J. Palm, Tetrahedron Asymmetry 21, 393 (2010) http://dx.doi.org/10.1016/j.tetasy.2010.02.015[Crossref]
• [27] S. Saravanakumar, PhD thesis (Ernst-Moritz-Arndt-University Greifswald, Greifswald, 2006)
• [28] J. Sun, S. Zhang, W. Cheng, J. Ren, Tetrahedron Letters 49, 3588 (2008) http://dx.doi.org/10.1016/j.tetlet.2008.04.022[Crossref]
• [29] M.T. Zarka, M. Bortenschlager, K. Wurst, O. Nuyken, R. Weberskirch, Organometallics 23, 4817 (2004) http://dx.doi.org/10.1021/om049495h[Crossref]
• [30] D.S. McGuinness, K.J. Cavell, Organometallics 19, 741 (2000) http://dx.doi.org/10.1021/om990776c[Crossref]
• [31] B.E. Ketz, A.P. Cole, R.M. Waymouth, Organometallics 23, 2835 (2004) http://dx.doi.org/10.1021/om049838b[Crossref]
• [32] B.E. Ketz, X.G. Ottenwaelder, R.M. Waymouth, Chem. Comm. 5693 (2005) [Crossref]
• [33] S. Benson, B. Payne, R.M. Waymouth, J. Polym. Sci., Part A, Polym. Chem. 45, 3637 (2007) http://dx.doi.org/10.1002/pola.22113[Crossref]
• [34] G.M. Sheldrick, Acta Cryst. A 64, 112 (2008) http://dx.doi.org/10.1107/S0108767307043930[Crossref]
• [35] W.A. Herrmann, L.J. Gooßen, M. Spiegler, J. Organomet. Chem. 547, 357 (1997) http://dx.doi.org/10.1016/S0022-328X(97)00434-8[Crossref]
• [36] H. Glas, E. Herdtweck, M. Spiegler, A.-K. Pleier, W.R. Thiel, J. Organomet. Chem. 626, 100 (2001) http://dx.doi.org/10.1016/S0022-328X(01)00655-6[Crossref]
• [37] P.L. Arnold, A.C. Scarisbrick, A.J. Blake, C. Wilson, Chem. Comm. 2340 (2001) [Crossref]
• [38] H. Clavier, L. Coutable, L. Toupet, J.-C. Guillemin, M. Mauduit, J. Organomet. Chem. 690, 5237 (2005) http://dx.doi.org/10.1016/j.jorganchem.2005.04.027[Crossref]
• [39] H. Clavier, L. Coutable, J.-C. Guillemin, M. Mauduit, Tetrahedron: Asym. 16, 921 (2005) http://dx.doi.org/10.1016/j.tetasy.2005.01.015[Crossref]
• [40] W.-F. Li, H.-M. Sun, Z.-G. Wang, M.-Z. Chen, Q. Shen, Y. Zhang, J. Organomet. Chem. 690, 6227 (2005) http://dx.doi.org/10.1016/j.jorganchem.2005.09.029[Crossref]
• [41] J. Heinicke, M. Koesling, R. Brüll, W. Keim, H. Pritzkow, Eur. J. Inorg. Chem. 299 (2000)
• [42] A.W. Waltman, T. Ritter, R.H. Grubbs, Organometallics 25, 4238 (2006) http://dx.doi.org/10.1021/om060528y[Crossref]
• [43] J. Heinicke, M. Köhler, N. Peulecke, M. He, M.K. Kindermann, W. Keim, G. Fink, Chem. Eur. J. 9, 6093 (2003) http://dx.doi.org/10.1002/chem.200304888[Crossref]
• [44] J. Heinicke, M. He, A. Dal, H.-F. Klein, O. Hetche, W. Keim, U. Flörke, H.-J. Haupt, Eur. J. Inorg. Chem. 431 (2000)
• [45] J. Heinicke, A. Dal, H.-F. Klein, O. Hetche, U. Flörke, H.-J. Haupt, Z. Naturforsch. B 54, 1235 (1999)
• [46] H.D. Empsall, B.L. Shaw, B.L. Turtle, J. Chem. Soc. Dalton Trans. 1500 (1976) [Crossref]
• [47] C.D. Abernethy, J.A.C. Clyburne, A.H. Cowley, R.A. Jones, J. Am. Chem. Soc. 121, 2329 (1999) http://dx.doi.org/10.1021/ja983772s[Crossref]
• [48] F.E. Hahn, B. Heidrich, A. Hepp, T. Pape, J. Organomet. Chem. 692, 4630 (2007) http://dx.doi.org/10.1016/j.jorganchem.2007.04.025[Crossref]
• [49] D.A. Malyshev, N.M. Scott, N. Marion, E.D. Stevens, V.P. Ananikov, I.P. Beletskaya, S.P. Nolan, Organometallics 25, 4462 (2006) http://dx.doi.org/10.1021/om060302v[Crossref]
• [50] W. Buchowicz, A. Koziol, L.B. Jerzykiewicz, T. Lis, S. Pasynkiewicz, A. Pecherzewska, A. Pietrzykowski, J. Mol. Catal. A: Chemical 257, 118 (2006) http://dx.doi.org/10.1016/j.molcata.2006.05.061[Crossref]
• [51] R.A. Kelly III, N.M. Scott, S. Diez-Gonzalez, E.D. Stevens, S.P. Nolan, Organometallics 24, 3442 (2005) http://dx.doi.org/10.1021/om0501879[Crossref]
• [52] C.D. Abernethy, R.J. Baker, M.L. Cole, A.J. Davies, C. Jones, Trans. Metal Chem. 28, 296 (2003) http://dx.doi.org/10.1023/A:1022979412307[Crossref]
• [53] C.D. Abernethy, A.H. Cowley, R.A. Jones, J. Organomet. Chem. 596, 3 (2000) http://dx.doi.org/10.1016/S0022-328X(99)00557-4[Crossref]
• [54] J. Heinicke, M. Köhler, N. Peulecke, M.K. Kindermann, W. Keim, M. Köckerling, Organometallics 24, 344 (2005) http://dx.doi.org/10.1021/om049474n[Crossref]
• [55] J. Heinicke, N. Peulecke, P.G. Jones, Chem. Commun. 262 (2005) [Crossref]
• [56] J. Lach, C.-Y. Guo, M.K. Kindermann, P.G. Jones, J. Heinicke, Eur. J. Org. Chem. 1176 (2010) [Crossref]

Identifiers

DOI

10.2478/s11532-010-0071-6