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2005 | 3 | 3 | 404-416
Tytuł artykułu

Rational design and convenient synthesis of a novel family of ruthenium complexes with O,N-bidentate ligands

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A two step procedure for the synthesis of a novel family of homogeneous and immobilized Ru-complexes containing Schiff bases as O,N-bidentate ligands is described. The new Ru-complexes have been structurally characterized by IR, Raman,1H-,13C-NMR spectroscopy. The Schiff bases were associated with a diversity of inorganic and organic ligands such as chloride, phosphane, arenes, various carbenes (alkylidene, vinylidene, indenylidene and allenylidene as well as N-heterocyclic carbenes) and cyclodienes. By choosing a selective range of substituents for the Schiff base, useful physical and chemical properties of the prepared Rucomplexes can be induced. This synthetic approach is promising in creating a valuable and diverse selection of Ru-complexes, valuable for future applications.
Wydawca

Czasopismo
Rocznik
Tom
3
Numer
3
Strony
404-416
Opis fizyczny
Daty
wydano
2005-09-01
online
2005-09-01
Twórcy
  • Department of Inorganic and Physical Chemistry, Laboratory of Organometallic Chemistry and Catalysis, Ghent University, Krijgslaan 281 (S-3), 9000, Ghent, Belgium
autor
  • Department of Inorganic and Physical Chemistry, Laboratory of Organometallic Chemistry and Catalysis, Ghent University, Krijgslaan 281 (S-3), 9000, Ghent, Belgium
autor
  • Department of Inorganic and Physical Chemistry, Laboratory of Organometallic Chemistry and Catalysis, Ghent University, Krijgslaan 281 (S-3), 9000, Ghent, Belgium
  • Institute of Organic Chemistry, Romanian Academy, Spl. Independentei 202B, Romania
  • Institute of Organic Chemistry, Romanian Academy, Spl. Independentei 202B, Romania
  • Department of Inorganic and Physical Chemistry, Laboratory of Organometallic Chemistry and Catalysis, Ghent University, Krijgslaan 281 (S-3), 9000, Ghent, Belgium, francis.verpoort@UGent.be
Bibliografia
  • [1] T. Opstal and F. Verpoort: “Synthesis of highly active ruthenium indenylidene complexes for atom-transfer radical polymerization and ring-opening-metathesis polymerisation”, Angew. Chem. Int. Ed., Vol. 42, (2003), pp. 2876–2879. http://dx.doi.org/10.1002/anie.200250840[Crossref]
  • [2] R.H. Grubbs (Ed.): Handbook of Metathesis, Vol. 1, Wiley-VCH, Weinheim, 2003.
  • [3] T.M. Trnka and R.H. Grubbs: “The development of L2X2Ru=CHR olefin metathesis catalysts: An organometallic success story”, Acc. Chem. Res., Vol. 34, (2001), pp. 18–29. http://dx.doi.org/10.1021/ar000114f[Crossref]
  • [4] E. Khosravi and T. Szymanska-Buzar (Eds.): ROMP and Related Chemistry: State of the Art and Visions for the New Century, NATO Advanced Study Institute (ASI), Kluwer Academic Publishers, Dordrecht, The Netherlands, 2002.
  • [5] A. Furstner (Ed.): Alkene Metathesis in Organic Synthesis, Springer, Berlin, 1998.
  • [6] A. Furstner: “Olefin metathesis and beyond”, Angew. Chem. Int. Ed., Vol. 112, (2000), pp. 3013–3043. http://dx.doi.org/10.1002/1521-3757(20000818)112:16<3013::AID-ANGE3013>3.0.CO;2-T[Crossref]
  • [7] K.J. Ivin and J.C. Mol: Olefin Metathesis and Metathesis Polymerization. Academic Press, London, 1997.
  • [8] Y. Imamoglu (Ed.): Metathesis polymerization of olefins and polymerization of alkynes, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1998.
  • [9] V. Dragutan and R. Streck: Catalytic Polymerization of Cyclo-olefins, Elsevier, Amsterdam, 2000.
  • [10] Y. Imamoglu and L. Bencze (Eds.): Novel Metathesis Chemistry: Well-defined Initiator Systems for Speciality Chemical Synthesis, Tailored Polymers and Advanced Material Applications, NATO Advanced Study Institute (ASI), Kluwer Academic Publishers, Dordrecht, The Netherlands, 2003.
  • [11] T. Weskamp, W.C. Schattenmann, M. Spiegler and W.A. Herrmann: “A novel class of ruthenium catalysts for olefin metathesis”, Angew. Chem. Int. Ed., Vol. 37, (1998), pp. 2490–2493. http://dx.doi.org/10.1002/(SICI)1521-3773(19981002)37:18<2490::AID-ANIE2490>3.0.CO;2-X[Crossref]
  • [12] L. Ackermann, A. Fürstner, T. Weskamp, F.J. Kohl and W.A. Herrmann: “Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM”, Tetrahedron Lett., Vol. 40, (1999), pp. 4787–4790. http://dx.doi.org/10.1016/S0040-4039(99)00919-3[Crossref]
  • [13] A.K. Chatterjee, J.P. Morgan, M. Scholl and R.H. Grubbs: “Synthesis of functionalized olefins by cross and ring-closing metatheses”, J. Am. Chem. Soc., Vol. 122, (2000), pp. 3783–3784. http://dx.doi.org/10.1021/ja9939744[Crossref]
  • [14] J. Huang, H.Z. Schanz, E.D. Stevens and S.P. Nolan: “Influence of sterically demanding carbene ligation on catalytic behavior and thermal stability of ruthenium olefin metathesis catalysts”, Organometallics, Vol. 18, (1999), pp. 5375–5380. http://dx.doi.org/10.1021/om990788y[Crossref]
  • [15] M.S. Sanford, J.A. Love and R.H. Grubbs: “A versitale precursor for the synthesis of new ruthenium olefin metathesis catalysts”, Organometallics, Vol. 20, (2001), pp. 5314–5318. http://dx.doi.org/10.1021/om010599r[Crossref]
  • [16] S.T. Nguyen and T.M. Trnka: “The discovery and development of well defined, ruthenium based olefin metathesis catalysts”, In: R.H. Grubbs (Ed.): Handbook of Metathesis, Vol. 1, Wiley-VCH, Weinheim, 2003.
  • [17] B. De Clercq and F. Verpoort: “Assessing the scope of the introduction of Schiff bases as co-ligands for monometallic and homobimetallic ruthenium ring-opening metathesis polymerisation and ring-closing metathesis initiators”, Adv. Synth. Catal., Vol. 344, (2002), pp. 639–648. http://dx.doi.org/10.1002/1615-4169(200208)344:6/7<639::AID-ADSC639>3.0.CO;2-0[Crossref]
  • [18] A. Demonceau, F. Simal and A.F. Noels: “Dual activity of ruthenium complexes in olefin metathesis and radical reactions”, In: E. Khosravi and T. Szymanska-Buzar (Eds.): ROMP and Related Chemistry: State of the Art and Visions for the New Century, NATO Advanced Study Institute (ASI), Kluwer Academic Publishers, Dordrecht, The Netherlands, (2002), pp. 227–246.
  • [19] D. Sémeril and P.H. Dixneuf: “The alkene metathesis ruthenium catalyst saga”, In: Y. Imamoglou and L. Bencze (Eds.): Novel Metathesis Chemistry: Well-defined Initiator Systems for Speciality Chemical Synthesis, Tailored Polymers, and Advanced Material Applications, NATO Advanced Study Institute (ASI), Kluwer Academic Publishers, Dordrecht, The Netherlands, 2003.
  • [20] R.H. Grubbs and S. Chang: “Recent advances in olefin metathesis and its application in organic synthesis”, Tetrahedron, Vol. 54, (1998), pp. 4413–4450. http://dx.doi.org/10.1016/S0040-4020(97)10427-6[Crossref]
  • [21] V. Dragutan, I. Dragutan and A.T. Balaban: “Single-Site Ruthenium Metathesis Catalysts”, Platinum Metals Rev., Vol. 45, (2001), pp. 155–163.
  • [22] S.J. Connon and S. Blechert: “Recent developments in olefin cross-metathesis”, Angew. Chem. Int. Ed., Vol. 42, (2003), pp. 1900–1923. http://dx.doi.org/10.1002/anie.200200556[Crossref]
  • [23] A. Deiters and S.F. Martin: “Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis”, Chem. Rev., Vol. 104, (2004), pp. 2199–2238. http://dx.doi.org/10.1021/cr0200872[Crossref]
  • [24] S.T. Diver and A.J. Giessert: “Enyne metathesis (enyne bond reorganization)”, Chem. Rev., Vol. 104, (2004), pp. 1317–1382. http://dx.doi.org/10.1021/cr020009e[Crossref]
  • [25] V. Dragutan and I. Draguta: “Ruthenium Vinylidene Complexes”, Platinum Metals Rev., Vol. 48, (2004), pp. 148–153. http://dx.doi.org/10.1595/147106704X4835[Crossref]
  • [26] S. Rigaut, D. Touchard and P.H. Dixneuf: “Ruthenium-allenylidene complexes and their specific behaviour”, Coord. Chem. Rev., Vol. 248, (2004), pp. 1585–1601. http://dx.doi.org/10.1016/j.ccr.2004.04.016[Crossref]
  • [27] B. De Clercq and F. Verpoort: “Ring-closing metathesis, Kharasch addition and enol ester synthesis catalysed by a novel class of ruthenium(II) complexes”, Tetrahedron Lett., Vol. 42, (2001), pp. 8959–8963. http://dx.doi.org/10.1016/S0040-4039(01)01952-9[Crossref]
  • [28] P.A. Vigato and S. Tamburini: “The challenge of cyclic and acyclic Schiff bases and related derivatives”, Coord. Chem. Rev., Vol. 248, (2004), pp. 1717–2128. http://dx.doi.org/10.1016/j.cct.2003.09.003[Crossref]
  • [29] B. De Clercq and F. Verpoort: “A new class of ruthenium complexes containing Schiff base ligands as promising catalysts for atom transfer radical polymerization and ring opening metathesis polymerisation”, J. Mol. Catal. A-Chemical, Vol. 180, (2002), pp. 67–76. http://dx.doi.org/10.1016/S1381-1169(01)00451-4[Crossref]
  • [30] T. Opstal, K. Couchez and F. Verpoort: “Easily accessible ring opening metathesis and atom transfer radical polymerization catalysts based on arene, norbornadiene and cyclooctadiene ruthenium complexes bearing Schiff base ligands”, Adv. Synth. Catal., Vol. 345, (2003), pp. 393–401. http://dx.doi.org/10.1002/adsc.200390045[Crossref]
  • [31] B. De Clercq and F. Verpoort: “Radical reactions catalysed by homobimetallic ruthenium(II) complexes bearing Schiff base ligands: atom transfer radical addition and controlled polymerisation”, Tet. Lett., Vol. 43, (2002), pp. 4687–4690. http://dx.doi.org/10.1016/S0040-4039(02)00834-1[Crossref]
  • [32] B. De Clercq and F. Verpoort: “Atom Transfer Radical Polymerization of Vinyl Monomers Mediated by Schiff Base Ruthenium-Alkylidene Catalysts and the Adventitious Effect of Water in Polymerizations with the Analogous Cationic Complexes”, Macromolecules, Vol. 35, (2002), pp. 8943–8947. http://dx.doi.org/10.1021/ma020307d[Crossref]
  • [33] B. De Clercq and F. Verpoort: “Atom transfer radical polymerization of vinyl monomers mediated by a new class of neutral and cationic ruthenium alkylidene catalysts containing a 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene and a Schiff base ligand”, Polymer Bulletin, Vol. 50, (2003), pp. 153–160. http://dx.doi.org/10.1007/s00289-003-0149-9[Crossref]
  • [34] B. De Clercq and F. Verpoort: “Synthesis and evaluation of a new class of ruthenium-based catalytic systems for atom transfer radical addition and enol ester synthesis”, J. Organomet Chem., Vol. 672, (2003), pp. 11–16. http://dx.doi.org/10.1016/S0022-328X(03)00055-X[Crossref]
  • [35] T. Opstal, and F. Verpoort: “Easily accessible and robust olefin-metathesis catalysts based on ruthenium vinylidene complexes”, J. Mol. Catal. A-Chem., Vol. 200, (2003), pp. 49–61. http://dx.doi.org/10.1016/S1381-1169(03)00099-2[Crossref]
  • [36] T. Opstal and F. Verpoort: “Synthesis of enol esters and dimerization of terminal alkynes catalyzed by neutral and cationic vinylidene ruthenium complexes”, Synlett., (2003), pp. 314–320.
  • [37] T. Opstal and F. Verpoort: “Atom transfer radical addition and enol-ester synthesis catalyzed by Ru-vinylidene complexes”, Tet. Lett., Vol. 43, (2002), pp. 9259–9263. http://dx.doi.org/10.1016/S0040-4039(02)02233-5[Crossref]
  • [38] T. Opstal and F. Verpoort: “Ruthenium indenylidene and vinylidene complexes bearing Schiff bases: Potential catalysts in enol-ester synthesis”, Synlett., (2002), pp. 935–941 [Crossref]
  • [39] T. Opstal and F. Verpoort: “From atom transfer radical addition to atom transfer radical polymerisation of vinyl monomers mediated by ruthenium indenylidene complexes”, New J. Chem., Vol. 27, (2003), pp. 257–262. http://dx.doi.org/10.1039/b210040a[Crossref]
  • [40] B. De Clercq, F. Lefebvre and F. Verpoort: “A new heterogeneous hybrid ruthenium catalyst being an eco-friendly option for the production of polymers and organic intermediates”, New J. Chem., Vol. 26, (2002), pp. 1201–1208. http://dx.doi.org/10.1039/b202872g[Crossref]
  • [41] B. De Clercq, F. Lefebvre and F. Verpoort: “Immobilization of multifunctional Schiff base containing ruthenium complexes on MCM-41”, Applied Catalysis A: General, Vol. 247, (2003), pp. 345–364. http://dx.doi.org/10.1016/S0926-860X(03)00126-1[Crossref]
  • [42] B. De Clercq, T. Smellinckx, C. Hughelier, N. Maes and F. Verpoort: “Monitoring of the polymerization of norbornene by in-line fiber-optic near IR-FT Raman”, Appl. Spectr., Vol. 55, (2001), pp. 1564–1567. http://dx.doi.org/10.1366/0003702011953829[Crossref]
  • [43] K. Melis, D. De Vos, P. Jacobs and F. Verpoort: “ROMP and RCM catalysed by (R3P)2Cl2Ru=CHPh immobilised on a mesoporous support”, J. Mol. Catal. A: Chemical, Vol. 169, (2001), pp. 47–56. http://dx.doi.org/10.1016/S1381-1169(00)00563-X[Crossref]
  • [44] B. De Clercq, T. Opstal, K. Melis and F. Verpoort: “Heterogenation of a Schiff base substituted Grubbs catalyst and Ru-dimer to perform ROMP reactions”, In: E. Khosravi and T. Szymanska-Buzar (Eds.): ROMP and Related Chemistry: State of the Art and Visions for the New Century, NATO Advanced Study Institute (ASI), Kluwer Academic Publishers, Dordrecht, The Netherlands, 2002, pp. 451–464.
  • [45] T. Opstal, K. Melis and F. Verpoort: “Atom transfer radical polymerisation with an immobilised [RuCl2(p-cymene)]2 dimmer”, Catal. Lett., Vol. 74, (2001), pp. 155–159. http://dx.doi.org/10.1023/A:1016643711546[Crossref]
  • [46] T. Opstal and F. Verpoort: “From atom transfer radical addition to atom transfer radical polymerisation of vinyl monomers mediated by ruthenium indenylidene complexes”, New J. Chem., Vol. 27, (2003), pp. 257–262. http://dx.doi.org/10.1039/b210040a[Crossref]
  • [47] B. De Clercq and F. Verpoort: “Kharasch addition and vinylation reactions mediated by ruthenium(II) complexes bearing Schiff base ligands”, Catal. Lett., Vol. 83, (2002), pp. 9–13. http://dx.doi.org/10.1023/A:1020688927811[Crossref]
  • [48] B. De Clercq and F. Verpoort: “Ring-closing metathesis, Kharasch addition and enol ester synthesis catalysed by a novel class of ruthenium(II) complexes”, Tet. Lett., Vol. 42, (2001), pp. 8959–8963. http://dx.doi.org/10.1016/S0040-4039(01)01952-9[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02479271
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