PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Powiadomienia systemowe
  • Sesja wygasła!
  • Sesja wygasła!
Tytuł artykułu

Dobrze zdefiniowane rutenowe katalizatory metatezy olefin

Autorzy
Identyfikatory
Warianty tytułu
EN
Well-defined ruthenium-based catalysts of olefin metathesis
Języki publikacji
PL
Abstrakty
EN
Olefin metathesis has become an important synthetic tool in organic and polymer chemistry. The family of ruthenium based catalysts tolerant of normal organic and polymer processing conditions and preserving their catalytic properties in the presence of the majority of functional groups has allowed a great number of new applications. The monograph gives a review of literature on well-defined ruthenium catalysts of olefin metathesis published till the end of 2004. The activity of catalytic systems based on different ruthenium complexes in metathetic reactions has been characterised. The methods of obtaining alkylidene complexes of ruthenium showing catalytic activity in olefin metathetic transformations have been described together with the reactions in which these compounds can be used as precatalysts. Because of a large body of literature data on Grubbs catalysts and their significance in synthesis, much space is devoted to them, including the methods of their synthesis and the known processes leading to their decomposition. Elements of the mechanism of olefin metathesis the presence of Grubbs catalysts of the 1st and 2nd generation are presented together with the consequences for designing of new catalysts of the process. The catalysts containing a chelating alkylidene ligand, in particular the Hoveyda-Grubbs catalysts arousing increasing interest and already commercially available, have been discussed. Moreover, the paper provides characterisation of the cationic alkylidene complexes described by Hoffmann, allenylidene, vinylidene and alkylidynehydride complexes described by Werner. Preliminary results on obtaining chiral alkylidene ruthenium catalysts and their use in the asymmetric synthesis are also presented. Regarding a number of prospective commercial applications of metathesis in organic synthesis, the current status of the study on heterogenization of alkylidene ruthenium complexes in order to obtain active and stable catalysts for multiple use was described. The paper ends with a list of the most important, in the opinion of the author, monographs and review works on the application olefin metathesis catalysed by well-defined alkylidene complexes in organic and polymer synthesis.
Rocznik
Strony
405--467
Opis fizyczny
Bibliogr. 301 poz., schem., tab.
Twórcy
  • Zakład Chemii Metaloorganicznej, Wydział Chemii, Uniwersytet im. Adama Mixckiewicza w Poznaniu, ul. Grunwaldzka 6, 60-780 Poznań
Bibliografia
  • [1] K.J. Ivin, J.C. Mol, Olefin Metathesis and Metathesis Polymerization, Academic Press, London, 1997, str. 1.
  • [2] W literaturze naukowej za pierwsze opublikowane przykłady procesów metatetycznych podaje się następujące patenty oraz publikacje: a) A.W. Anderson, N.G. Merckling, US Patent, 2721189 z 1955 roku, dotyczący polimeryzacji norbomenu.
  • b) H.S. Eleuterio, US Patent, 3074918 z 1957 roku, dotyczący polimeryzacji cykloalkenów. c) W.L. Truett, D.R. Johnson, M. Robinson, B.A. Montague, J. Am. Chem. Soc., 1960, 82, 2337 dotyczącą polimeryzacji norbomenu. d) R.L. Banks, G.C. Bailey, Ind. Eng. Chem. Prod. Res. Dev., 1964, 3, 170 dotyczącą metatezy propenu.
  • [3] K.J. Ivin, Olefin Metathesis, Academic Press, London, 1983, rozdział 18.
  • [4] N. Calderon et al., Chem. Eng. News, 1967, 45, 51.
  • [5] J.-L. Herisson, Y. Chauvin, Macromol. Chem., 1971, 141, 161.
  • [6] R.R. Schrock, Acc. Chem. Res., 1990, 23,158.
  • [7] E.O. Fischer, A. Maasbol, Angew. Chem., 1964,76, 645.
  • [8] F.N. Tebbe, G.W. Parschal, S.N.J. Reddy, J. Am. Chem. Soc., 1978,100, 3611.
  • [9] T.R. Howard, J.B. Lee, R.H. Grubbs, J. Am. Chem. Soc., 1980,102, 6876.
  • [10] L.R. Gilliom, R.H. Grubbs, J. Am. Chem. Soc., 1986,108, 733.
  • [11] S.M. Rocklage, J.D. Fellmann, G.A. Rupprecht, L.W. Messerle, R.R. Schrock, J. Am. Chem. Soc., 1981, 103, 1440.
  • [12] K.C. Wallace, R.R. Schrock, Macromolecules, 1987, 20, 450.
  • [13] K.C. Wallace, A.H. Liu, J.C. Dewan, R.R. Schrock, J. Am. Chem. Soc., 1988, 110,4964.
  • [14] W.R. Kroll, G. Doyle, J. Chem. Soc., Chem. Commun., 1971, 839.
  • [15] Y. Chauvin, D. Commereuc, D. Cruypelinck, Macromol. Chem., 1976, 177, 2637.
  • [16] TJ. Katz, SJ. Lee, N. Acton, Tetrahedron Lett., 1976, 4247
  • [17] T.J. Katz, W.H. Hersh, Tetrahedron Lett., 1977, 585.
  • [18] J. Kress, M. Wesołek, J.A. Osborn, J. Chem. Soc., Chem. Commun., 1982, 514.
  • [19] J.L Kress, J.A. Osborn, J. Am. Chem. Soc., 1983, 105, 6346.
  • [20] R.R. Schrock, J Feldman, L.F. Canizzo, R.H. Grubbs, Macromolecules, 1987,20, 1169.
  • [21] C.J. Shaverien, J.C. Dewan, R.R. Schrock, J. Am. Chem. Soc., 1986, 108, 2771.
  • [22] R.R. Schrock, R.T. DePue, J. Feldman, CJ. Shaverien, J.C. Dewan, A.H. Liu, J. Am. Chem. Soc., 1988, 110, 1423.
  • [23] F. Quignard, M. Leconte, J.M. Basset, J. Chem. Soc., Chem. Commun., 1985, 1816.
  • [24] F. Quignard, M. Leconte, J.M. Basset, J. Mol. Catal., 1986, 36, 13.
  • [25] D. Boutarfa, C. Paillet, M. Leconte, J.M. Basset, J. Mol. Catal., 1991, 69, 157.
  • [26] J.M. Basset, From Ill-Defined to Well-Defined W Alkylidene Complexes, [w:] Handbook of Metathesis, R.H. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdział 1.4.
  • [27] J.S. Murdzek, R.R. Schrock, Organometallics, 1987, 6, 1373.
  • [28] J.H. Oskam, H.H. Fox, K.B. Yap, D.H. McConville, R,0'Dell, B.J. Lichtenstein, RR. Schrock, J. Organomet. Chem., 1993, 459, 185.
  • [29] R.R. Schrock, S. Luo, J.J.C. Lee, J.N.C. Zanetti, W.M. Davis, J. Am. Chem. Soc., 1996, 118,3883.
  • [30] R.R. Schrock, Tetrahedron, 1999, 55, 8141.
  • [31] J.S. Murdzek, R.R. Schrock, Macromolecules, 1987, 20,2640.
  • [32] R.R. Schrock, J.S. Murdzek, G.C. Bazan, J. Robins, M. DiMare, M. O'Regan, J. Am. Chem. Soc., 1990, 112, 3875.
  • [33] J. Konzelman, K.B. Wagener, Macromolecules, 1995, 28, 4686.
  • [34] E. Thom-Csanyi, K.P. Pflug, Macromol. Chem., Rapid. Commun., 1993, 14, 619.
  • [35] R.R. Schrock, S. Luo, N.C. Zanetti, H.H. Fox, Organometallics, 1994, 13, 3396.
  • [36] S. Koltzenburg, E. Eder, F. Stelzer, O. Nuyken, Macromolecules, 1999, 32, 21.
  • [37] H.H. Fox, R.R. Schrock, Organometallics, 1992, 11, 2763.
  • [38] H.H. Fox, M.O. Wolf, R. O'Dell, B.L. Lin, R R Schrock, M.S. Wrighton, J. Am. Chem. Soc., 1994, 116, 2827.
  • [39] F.J. Schattenmann, R.R. Schrock, W.M. Davis, J. Am. Chem. Soc., 1996, 118, 3295.
  • [40] M. Buchmeiser, Chem. Rev., 2000, 100, 1565.
  • [41] G. Black, D. Maher, W. Risse, Living Ring Opening Metathesis Polymerization, [w:] Handbook of Metathesis, R.H. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdział 3.2.
  • [42] R.R. Schrock, A.H. Hoveyda, Angew. Chem., Int. Ed., 2003, 42, 4592.
  • [43] R.R. Schrock, Olefin Metathesis by Well-Defined Complexes of Molybdenum and Tungsten, [w:] Alkene Metathesis in Organic Synthesis, A. Fürstner, Ed., Springer, Berlin, 1998, s. 1.
  • [44] A.H. Hoveyda, R.R. Schrock, Chem. Eur. J., 2001, 7, 945.
  • [45] Z. Wu, D.R. Wheeler, R.H. Grubbs, J. Am. Chem. Soc., 1992, 114, 146.
  • [46] S.K. Armstrong, B.A. Christie, Tetrahedron Lett., 1996, 37, 9373.
  • [47] Y.S. Shon, T.R. Lee, Tetrahedron Lett., 1997, 38, 1283.
  • [48] W.E. Crowe, D.R. Goldberg, J. Am. Chem. Soc., 1995, 117, 5162.
  • [49] G.C. Fu, R.H. Grubbs, J. Am. Chem. Soc., 1993,115, 3800.
  • [50] R. Toreki, G.A. Vaughan, R.R. Schrock, W.M. Davies, J. Am. Chem. Soc., 1993, 115, 127.
  • [51] T.M. Trnka, R.H. Grubbs, Acc. Chem. Res., 2001, 34, 18.
  • [52] M.L.H. Green, M.C. Mitchard, M.G. Swanwick, J. Chem. Soc. (A), 1971, 794.
  • [53] W.R. Roper, J. Organomet. Chem., 1986, 300, 167.
  • [54] S.T. Nguyen, L.K. Johnson, R.H. Grubbs, J.W. Ziller, J. Am. Chem. Soc., 1992, 114, 3974.
  • [55] M.A. Gallop, W.R. Roper, Adv. Organomet. Chem., 1986, 25, 121.
  • [56] A.F. Hill, Mononuclear Complexes of Ruthenium and Osmium Containing I Carbon Ligands, [w:] Comprehensive Organometallic Chemistry II, E.W. Abel, F.G.A. Stone, G. Wilkinson, Eds., Pergamon, London, 1995, vol. 7, rozdział 6.
  • [57] G. Natta, G. Dall'Asta, G. Motroni, J. Polym. Sei. (B) 1964, B 2,349.
  • [58] G. Natta, G. Dall'Asta, L. Porri, Macromol. Chem., 1965, 81, 253.
  • [59] F.W. Michelotti, W.P. Keaveney, J. Polym. Sei. (A), 1965, 3, 895.
  • [60] R.E. Rinehart, H.P. Smith, J. Polym. Sei., Part B: Polym. Lett., 1965, 3, 1049.
  • [61] B.M. Novak, R.H. Grubbs, J. Am. Chem. Soc., 1988, 110, 960.
  • [62] E. Zenki, F. Stelzer, J. Mol. Catal., 1992, 76, 1.
  • [63] S.-Y. Lu, P. Quavle, F. Heatley, C. Booth, S.G. Yeates, J.C. Padget, Macromolecules. 1992, 25, 2692.
  • [64] W.J. Feast, D.B. Harrison, J. Mol. Catal., 1991, 65, 63.
  • [65] B.M. Novak, R.H. Grubbs, J. Am. Chem. Soc., 1988, 110, 7542.
  • [66] M.A. Hillmyer, C. Lepetit, D.V. McGrath, B.M. Novak, R.H. Grubbs, Macromolecules, 1992,25, 3345.
  • [67] D.V. McGrath, R.H. Grubbs, J.W. Ziller, J. Am. Chem. Soc., 1991, 113, 3611.
  • [68] T. Karlen, A. Ludi, A. Muhlebach, P. Bernhard, C. Pharisa. J. Polym. Sei., Part. A: Polym. Chem., 1995, 33, 1665.
  • [69] A. Hafner, P.A. van der Schaaf, A. Muhlebach, Chimia, 1996, 50, 131.
  • [70] L. Porri, R. Rossi, P. Diversi, A. Lucherini, Macromol. Chem., 1974, 175, 3097.
  • [71] L. Porri, P. Diversi, A. Lucherini, R. Rossi, Macromol. Chem., 1975, 176, 3121.
  • [72] K.J. Ivin, B.S.R. Reddy, J.J. Rooney, J. Chem. Soc., Chem. Commun., 1981, 1062.
  • [73] M.B. France, R.A. Paciello, R.H. Grubbs, Macromolecules, 1993, 26, 4739.
  • [74] A. Demonceau, A.F. Noels. E. Saive, A.J. Hubert, J. Mol. Catal., 1992, 76, 123.
  • [75] A.W. Stumpf, E. Saive, A. Demonceau, A.F. Noels, J. Chem. Soc., Chem. Commun., 1995, 1127.
  • [76] A. Demonceau, A.W. Stumpf, E. Saive, A.F. Noels, Macromolecules, 1997, 30, 3127.
  • [77] L. Delaude, A. Demonceau. A.F. Noels, Macromolecules, 1999, 32, 2091.
  • [78] P. Lecomte, D. Mecerreyes, P. Dubois, A. Demonceau, A.F. Noels, R. Jerome, Polym. Bull., 1998, 40, 631.
  • [79] K. Hiraki, A. Kuroiwa, H. Hirai, J. Pol. Sei. (A), 1971, 9, 2323.
  • [80] S. Wache, W.A. Herrmann, G. Artus, O. Nuyken, D. Wolf, J. Organomet. Chem., 1995, 491 181.
  • [81] W.A. Herrmann, W.C. Schattenmann O. Nuyken, S.C. Glander, Angew. Chem., Int. Ed. Eng., 1996, 35, 1087.
  • [82] S.C. Glander, O. Nuyken, W.C. Schattenmann W.A. Herrmann, Macromol. Symp. 1998,127, 67.
  • [83] A.F. Noels, A. Demonceau, E. Carlier, A.J. Hubert, R.-L. Marquez-Silva, R.A. Sanchez-Delgado, J. Chem. Soc, Chem. Commun., 1988, 783.
  • [84] M.S. Sanford, M. Ulman, R.H. Grubbs, J. Am. Chem. Soc., 2001,123, 749.
  • [85] M.S. Sanford, J. A. Love, R. H. Grubbs, J. Am. Chem. Soc., 2001,123, 6543.
  • [86] M.S. Sanford, J.A. Love, Mechanism of Ruthenium-Catalyzed Olefin Metathesis Reactions, [w:] Handbook of Metathesis, R.H. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdział 1.9.
  • [87] E.L. Dias, S.T. Nguyen, R.H. Grubbs, J. Am. Chem. Soc., 1997,119, 3887.
  • [88] C. Adlhart, M.A.O. Volland, P. Hofmann, P. Chen, Helv. Chim. Acta, 2000, 83, 3306.
  • [89] C. Adlhart, C. Hinderling, H. Baumann, P. Chen, J. Am. Chem. Soc., 2000, 122, 8204.
  • [90] C. Hinderling, C. Adlhart, P. Chen, Angew. Chem., Int. Ed., 1998, 37, 2685.
  • [91] M.A.O. Volland, C. Adlhart, G.A. Kiener, P. Chen, P. Hofmann, Chem. Eur. J., 2001, 7, 4621.
  • [92] J.A. Tallarico, P.J. Bonitatebus, M.L. Snapper, J. Am. Chem. Soc. 1997, 119, 7157.
  • [93] R.H. Grubbs, T.M. Trnka, Ruthenium-Catalyzed Olefin Metathesis, [w:] Ruthenium in Organic Synthesis, S.-I. Murahashi, Ed., Wiley-VCH, Weinheim, 2004, rozdział 6.
  • [94] S.T. Nguyen, T.M. Trnka, The Discovery and Development of Well-Defined, Ruthenium Based Olefin Metathesis Catalysts, [w:] Handbook of Metathesis, R.H. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdział 1.6.
  • [95] C.W. Bielawski, R.H. Grubbs, Macromolecules, 2001, 34,8838.
  • [96] S.T. Nguyen, R.H. Grubbs, J.W. Ziller, J. Am. Chem. Soc., 1993, 115, 9858.
  • [97] C.A. Tolman, Chem. Rev., 1977, 77, 313.
  • [98] J. Feldman, R.R. Schrock, Prog. Inorg. Chem., 1991, 39, 1.
  • [99] R.R Schrock, Acc. Chem. Res., 1986, 19, 342.
  • [100] M.E. Cucullu, C. Li, S.P. Nolan, S.T. Nguyen, R.H. Grubbs, Organometallics, 1998, 17, 5565.
  • [101] G.C. Fu, S.T. Nguyen, J. Am. Chem. Soc., 1993, 115, 9856.
  • [102] S. Miller, R.H. Grubbs, J. Am. Chem. Soc., 1995, 117, 5855.
  • [103] B.C. Borer, S. Deerenberg, H. Bieräugei, U.K. Pandit, Tetrahedron Lett., 1994, 35, 3191.
  • [104] S. Kanaoka, R.H. Grubbs, Macromolecules, 1995, 28, 4707.
  • [105] M.A. Hillmyer, W.L. Laredo, R.H. Grubbs, Macromolecules, 1995, 28, 6311.
  • [106] B.R. Maughon, R.H. Grubbs, Polymer Prepr., 1995, 37, 471.
  • [107] A. Kinoshita, A. Mori, Synlett, 1994, 1020.
  • [108] P. Schwab, M.B. France, J.W. Ziller, R.H. Grubbs, Angew. Chem., Int. Ed. Eng. 1995, 34, 2039.
  • [109] P. Schwab, R.H. Grubbs, J.W. Ziller, J. Am. Chem. Soc., 1996,118, 100.
  • [110] S.-Y. Hang, S. Chang, General Ring Closing Metathesis, [w:] Handbook of Metathesis, R.H. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdział 2.2.
  • [111] M. Mori, Ene-Yne Metathesis, [w:] Handbook of Metathesis, R.H. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdział 2.5.
  • [112] S.E. Lehman, Jr, K.B. Wagener, ADMET Polymerization, [w:] Handbook of Metathesis, R.H. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdział 3.9.
  • [113] U. Frenzel, O. Nuyken, J. Pol. Sei., Polym. Chem., 2002, 40, 2895.
  • [114] G. Black, D. Maher, W. Risse, Living Ring Opening Metathesis Polymerization, [w:] Handbook of Metathesis, R.H. Grubbs. Ed., Wiley-VCH, Weinheim, 2003, rozdział 3.2.
  • [115] M. Scholl, S. Ding, C.W. Lee, R.H. Grubbs, Org. Lett., 1999, 1, 953.
  • [116] A.K. Chatterjee, T.L. Choi, D.R. Sanders, R.H. Grubbs, J. Am. Chem. Soc., 2003, 125, 11360.
  • [117] D.L. Boger, J. Hong, J. Am. Chem. Soc., 2001, 123, 8515.
  • [118] H.E. Blackwell, D.J. O’Leary, A.K. Chatterjee, R.A. Washenfelder, D.A. Bussmann, R.H. Grubbs, J. Am. Chem. Soc., 2000, 122, 58.
  • [119] O. Brummer, A. Ruckert, S. Blechert, Chem. Eur. J., 1997, 3, 441.
  • [120] Z. Wu, S.T. Nguyen, RH. Grubbs, J.W. Ziller, J. Am. Chem. Soc., 1995, 117, 5503.
  • [121] G.S. Forman, A.E. McConnell, M.J. Hanton, A.M.Z. Slawin, R.P. Tooze, W.J. van Rensburg, W.H. Meyer, C. Dwyer, M.M. Kirk, D.W. Serfontein, Organometallics, 2004, 23, 4824.
  • [122] A. Fürstner, J. Grabowski, C.W. Lehmann, J. Org. Chem., 1999, 64, 8275.
  • [123] A. Fürstner, O. Guth, A. Düffels, G. Seidel, M. Liebl, B. Gabor, R. Mynott, Chem. Eur. J., 2001, 7, 4811.
  • [124] A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C.W. Lehmann, R. Mynott, J. Am. Chem. Soc., 2002, 124, 7061.
  • [125] W. Stüer, J. Wolf, H. Werner, J. Organometal. Chem., 2002, 641, 203.
  • [126] B. Mohr, D.M. Lynn, R.H. Grubbs, Organometallics, 1996, 15, 4317.
  • [127] D.M. Lynn, B. Mohr, R.H. Grubbs, J. Am. Chem. Soc., 1998, 120, 1627.
  • [128] D.M. Lynn, B. Mohr, R.H. Grubbs, M. Henling, M.W. Day, J. Am. Chem. Soc., 2000, 122, 6601.
  • [129] T. Rolle, R.H. Grubbs, Chem. Commun., 2002, 1070.
  • [130] D.A. Robson, V.C. Gibson, R.G. Davies, M. North, Macromolecules, 1999, 32, 6371.
  • [131] E.L. Dias, RH. Grubbs, Organometallics, 1998, 17, 2758.
  • [132] M. Ulman, R.H. Grubbs, J. Org. Chem., 1999, 64, 7202.
  • [133] S. Chang, L. Jones, II, C. Wang, L.M. Henling, R.H. Grubbs, Organometallics, 1998, 17, 3460.
  • [134] M.S. Sanford, L.M. Henling, M.W. Day, R.H. Grubbs, Angew. Chem., Int. Ed., 2000, 39, 3451.
  • [135] W.R. Roper, Synthesis of Ruthenium Carbene Complexes, [w:] Handbook of Metathesis, R.h. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdział 1.7.
  • [136] T. Wilhelm, T.R. Belderrain, S.N. Brown, R.H. Grubbs, Organometallics, 1997, 16. 3867.
  • [137] M.A.O. VoIIand, F. Rominger, F. Eisentrager, P. Hofmann, J. Organomet-Chem. 2002, 641, 220.
  • [138] J. Wolf, W. Stüer, C. Grunwald, H. Werner, P. Schwab, M. Schulz, Angew. Chem., Int. Ed., 1998,37, 1124.
  • [139] M. Olivan, K.G. Caulton, Chem. Commun., 1997, 1733.
  • [140] T.R. Belderrain, R.H. Grubbs, Organometallics, 1997, 16, 4001.
  • [141] M. Gandelman, B. Rybtchinski, N. Ashkenazi, R.M. Gauvin, D. Milstein, J. Am. Chem. Soc., 2001, 123, 5372.
  • [142] P.A. van der Schaaf, R. Kolly, A. Hafner, Chem. Commun, 2000, 1045.
  • [143] R. Dorta, R.A. Kelly, S.P. Nolan, Adv. Synth. Catal., 2004, 346, 917.
  • [144] AJ. Arduengo, III, R.L. Harlow, M. Kline, J. Am. Chem. Soc., 1991, 131, 361.
  • [145] A.J. Arduengo, III, Acc. Chem. Res., 1999, 32, 913.
  • [146] D. Bourissou, O. Guerret, F. Gabbai, G. Bertrand, Chem. Rev. 2000, 100, 39.
  • [147] W.A. Herrmann, Angew. Chem., Int. Ed., 2002, 1291.
  • [148] W.A. Herrmann, T. Weskamp, V.P.W. Bohm, Adv. Organomet. Chem., 2001, 48, 1.
  • [149] T. Weskamp, V.P.W. Bohm, W.A. Herrmann, J. Organomet. Chem., 2000, 600, 12.
  • [150] W.A. Herrmann, C. Kocher, Angew. Chem., Int. Ed., 1997, 36, 2163.
  • [151] L. Jafarpour, S.P. Nolan, J. Organomet. Chem., 2001, 617-618, 17.
  • [152] L. Jafarpour, S.P. Nolan, Adv. Organomet. Chem., 2001, 48, 181.
  • [153] T. Weskamp, W.C. Schattenmann, M. Spiegler, W.A. Herrmann, Angew. Chem., Int. Ed., 1998, 37, 2490.
  • [154] M. Scholl, T. Trnka, J.P. Morgan, R.H. Grubbs, Tetrahedron Lett., 1999, 40, 2247.
  • [155] T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W.A. Herrmann, Angew. Chem., Int. Ed., 1999, 38, 2416
  • [156] T. Weskamp, F.J. Kohl, W.A. Herrmann, J. Organomet. Chem. 1999, 582, 362.
  • [157] J. Juang, H.-J. Schanz, E.D. Stevens, S.P. Nolan. Organometallics, 1999, 18, 5375.
  • [158] J. Juang, E.D. Stevens, S.P. Nolan, J.L. Petersen, J. Am. Chem. Soc., 1999, 121, 2674.
  • [159] L. Ackermann, A. Furstner, T. Weskamp, F.J. Kohl, W.A. Herrmann, Tetrahedron Lett, 1999, 40, 4787.
  • [160] A. Fürstner, O.R. Thiel, L. Ackermann, H.-J. Schanz, S.P. Nolan, J. Org. Chem., 2000, 65, 2204.
  • [161] A. Briot, M. Bujard, V. Gouverneur, S.P. Nolan, C. Mioskowski, Org. Lett., 2000, 2, 1517.
  • [162] C.W. Bielawski, R.H. Grubbs, Angew. Chem., Int. Ed., 2000,39,2903.
  • [163] S. BouzBouz, R. Simmons, J. Cossy, Org. Lett., 2004, 6, 3465.
  • [164] T.L. Choi, A.K. Chatteijee, R.H. Grubbs, Angew. Chem., Int. Ed., 2001, 40, 1277.
  • [165] A.K. Chatterjee, J.P. Morgan, M. Scholl, R.H. Grubbs, J. Am. Chem. Soc., 2000,122, 3783.
  • [166] A.K Chatteijee, R.H. Grubbs, Org. Lett., 1999,1, 1751.
  • [167] R. Stragies, U. Voigtmann, S. Blechert, Tetrahedron Lett., 2000, 41, 5465.
  • [168] S. Stinson, Chem. Eng. News., 2000, 78, 6.
  • [169] A. Furstner, L. Ackermann, B. Gabor, R. Goddard, C.W. Lehmann, R. Mynott, F. Stelzer, O.R. Thiel, Chem. Eur. J., 2001, 7, 3236.
  • [170] L. Jafarpour, H.-J. Schanz, E.D. Stevens, S.P. Nolan, Organometallics, 1999, 18, 5416.
  • [171] L. Jafarpour, E.D. Stevens, S.P. Nolan, J. Organomet. Chem., 2000, 606, 49.172] M.B. Dinger, J.C. Mol, Adv. Synth. Catal., 2002, 344, 671.
  • [173] M.B. Dinger, P. Nieczypor, J.C. Mol, Organometallics, 2003, 22, 5291.
  • [174] C.W. Bielawski, D. Benitez, R.H. Grubbs, J. Am. Chem. Soc., 2003, 125, 8424.
  • [175] S. Prühs, C.W. Lehmann, A. Furstner, Organometallics, 2004, 23, 280.
  • [176] J. Yun, E.R. Marinez, R.H. Grubbs, Organometallics, 2004, 23, 4172.
  • [177] M.S. Sanford, J.A. Love, R.H. Grubbs, Organometallics, 2001, 20, 5314.
  • [178] J.A. Love, M.S. Sanford, M.W. Day, R.H. Grubbs, J. Am. Chem. Soc. 2003, 125, 10103.
  • [179] S.H. Hong, M.W. Day, R.H. Grubbs, J. Am. Chem. Soc., 2004, 126, 7414.
  • [180] M. Kim, M.-S. Eum, M.Y. Jin, K.-W. Jun, C.W. Lee, K.A. Kuen, C.H. Kim, C.S. Chin, J. Organomet. Chem., 2004, 689, 3535.
  • [181] S.D. Drouin, G.P.A. Yap, D.E. Fogg, Inorg. Chem., 2000, 39, 5412.
  • [182] J. Louie, R.H. Grubbs, Organometallics, 2002, 21, 2153.
  • [183] M.B. Dinger, J.C. Mol, Organometallics, 2003, 22, 1089.
  • [184] M.B. Dinger, J.C. Mol, Eur. J. Inorg. Chem., 2003. 2827.
  • [185] T.M. Trnka, J.P. Morgan, M.S. Sanford, T.M. Wilhelm, M. Scholl, T.-L. Choi, S. Ding, M.W. Day, R.H. Grubbs, J. Am. Chem. Soc., 2003,125, 2546.
  • [186] H. Werner, C. Grünwald, W. Stüer, J. Wolf, Organometallics, 2003, 22, 1558.
  • [187] C. Pietraszuk, B. Marciniec, H. Fischer, Organometallics, 2000, 29, 913.
  • [188] C. Pietraszuk, B. Marciniec, H. Fischer, Tetrahedron Lett., 2003, 44, 7121.
  • [189] C. Pietraszuk, H. Fischer, Chem. Commun., 2000, 2463.
  • [190] C. Pietraszuk, H. Fischer, Organometallics, 2001, 20, 4641.
  • [191] B. Marciniec, M. Kujawa, C. Pietraszuk, New J. Chem., 2000, 24, 671.
  • [192] B. Schmidt, Eur. J. Org. Chem., 2004, 1865.
  • [193] B. Alcaide, P. Almendros, Chem. Eur. J., 2003, 9, 1259.
  • [194] J.C. Conrad, D. Amoroso, P. Czechura, G.P.A. Yap, D.E. Fogg, Organometallics, 2003, 22, 3634.
  • [195] J.A. Love, J.P. Morgan, T.M. Trnka, R.H. Grubbs, Angew. Chem., Int. Ed., 2002, 41, 4035.
  • [196] P.E. Romero, W.E. Piers, R. McDonald, Angew. Chem., Int. Ed., 2004, 6161.
  • [197] H. Katayama, H. Urushima, T. Nishioka, C. Wada, M. Nagao, F. Ozawa, Angew. Chem., Int. Ed. 2000, 39, 4513.
  • [198] H. Katayama, M. Nagao, F. Ozawa, Organometallics, 2003, 22, 586.
  • [199] H. Katayama, Y. Fukuse, Y. Nobuto, K. Akamatsu, F. Ozawa, Macromolecules, 2003, 36, 7020.
  • [200] P.A. van der Schaaf, R. Kolly, H.-J. Kimer, F. Rime, A. Mühlebach, A. Hafner, J. Organomet. Chem., 2000, 606, 65.
  • [201] J.S. Kingsburry, J.P.A. Harrity, A.H. Hoveyda, J. Am. Chem. Soc., 1999, 121, 791.
  • [202] A.H. Hoveyda, D.G. Gillingham, J.J. Van Veldhuizen, O. Kataoka, S.B. Garber, J.S. Kingsbury, J.P.A. Harrity, Org. Biomol. Chem., 2004, 2, 8.
  • [203] N. Audic, H. Clavier, M. Mauduit, J.-C. Guillemin, J. Am. Chem. Soc., 2003, 125, 9248.
  • [204] Q. Yao, Y. Zhang, Angew. Chem., Int. Ed., 2003, 42, 3395.
  • [205] S. Gatard, S. Nlate, E. Cloutet, G. Bravic, J.-C. Blais, D. Astruc, Angew. Chem., Int. Ed., 2003,42, 452.
  • [206] S. Gatard, S. Kahlal, D. Mery, S. Nlate, E. Cloutet, J.-Y. Saillard, D. Astruc, Organometallics, 2004, 23, 1313.
  • [207] S.B. Garber, J.S. Kingsburry, B.L. Gray, A.H. Hoveyda, J. Am. Chem. Soc., 2000 ,122, 8168.
  • [208] S. Gessler, S. Randl, S. Blechert, Tetrahedron Lett., 2000, 9973.
  • [209] S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett, 2001, 430.
  • [210] S. Imhof, S. Randl, S. Blechert, Chem. Commun., 2001, 1692.
  • [211] S. BouzBouz, E. De Lemos, J. Cossy, Adv. Synth. Catal., 2002, 344, 627.
  • [212] S. BouzBouz, J. Cossy, Org. Lett., 2001, 3, 1451.
  • [213] H. Mizutani, S.J. Degrado, A.H. Hoveyda, J. Am. Chem. Soc., 2001, 123, 627.
  • [214] B. Nosse, R.B. Chhor, W.B. Jeong, C. Bohm, O. Reiser, Org. Lett., 2003, 5, 941.
  • [215] S. Randl, S.J. Connon, S. Blechert, Chem. Commun., 2001, 1796.
  • [216] H. Wakamatsu, S. Blechert, Angew. Chem., Int. Ed., 2002, 41, 794.
  • [217] H. Wakamatsu, S. Blechert, Angew. Chem., Int. Ed., 2002, 41, 2403.
  • [218] A.M. Dunne, S. Mix, S. Blechert, Tetrahedron Lett., 2003, 44, 2733.
  • [219] M. Zaja, S.J. Connon, A.M. Dunne, M. Rivard, N. Buschmann, J. Jiricek, S. Blechert, Tetrahedron. 2003, 59, 6545.
  • [220] R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos, K. Grela, J. Am. Chem. Soc. 2004.126.9318.
  • [221] N. Buschmann, H. Wakamatsu, S. Blechert, Synlett, 2004, 667.
  • [222] S J. Connon, M. Rivard, M. Zaja, S. Blechert, Adv. Synth. Catal., 2003, 45, 572.
  • [223] K. Grela, S. Harutyunyan, A. Michrovvska, Angevv. Chem., Int. Ed., 2002, 41.4038.
  • [224] K. Grela, M. Kim, Eur. J. Org. Chem., 2003, 963.
  • [225] R. Bujok, M. Bieniek, M. Masnyk, A. Michrovvska, A. Surosiek, H. Stępowski, D. Arlt, K. Grela, J. Org. Chem., 2004, 69, 6894.
  • [226] L. Yang, M. Mayr, K. Wurst, M.R. Buchmeiser, Chem. Eur. J., 2004, 10, 5761.
  • [227] J.O. Krause, O. Nuyken, K. Wurst, M.R. Buchmeiser, Chem. Eur. J., 2004,10, 777.
  • [228] J.O. Krause, M.T. Zarka, U. Anders, R. Weberskirch, O. Nuvken, M.R. Buchmeiser. Angevv. Chem., Int. Ed., 2003, 42, 5965.
  • [229] J.O. Krause, O. Nuyken, M.R. Buchmeiser, Chem. Eur. J., 2004,10, 2029.
  • [230] A. Fürstner, O.R. Thiel, C.W. Lehman, Organometallics, 2002, 21, 331.
  • [231] C. Slugovc, B. Pemer, E Stelzer, K. Mereiter, Organometallics, 2004, 23, 3622.
  • [232] T. Ung, A. Hejl, R.H. Grubbs, Y. Schrodi, Organometallics, 2004,23, 5399.
  • [233] K. Denk, J. Fridgen, W.A. Herrmann, Adv. Synth. Catal., 2002, 344, 6 6 6 .
  • [234] H. Katayama, F. Ozawa, Coord. Chem. Rev., 2004, 248, 1703.
  • [235] C. Bruneau, Ruthenium Vinylidenes and Allenylidenes in Catalysis, [w:] Ruthenium Catalyst and Fine Chemistry, C. Bruneau, P.H. Dixneuf, Eds., Springer, Berlin, 2004, s. 125.
  • [236] H. Katayama, F. Ozawa, Organometallics, 1998, 17, 5190.
  • [237] Y. Wakatsuki, H. Yamazaki, N. Kumegavva, T. Satoh, J.Y. Satoh, J. Am. Chem. Soc., 1991, 113, 9604.
  • [238] C. Griinvvald. O. Gevert, J. Wolf, P. Gonzales-Herrero, H. Werner, Organometallics, 1996, 15, 1960.
  • [239] J. Wolf, W. Stüer, C. Grunwald, O. Gevert, M. Laubender, H. Wemer, Eur. J. Inorg. Chem., 1998, 1827.
  • [240] S. Jung, K. Ilg, C.D. Brandt, J. Wolf, H. Werner, Eur. J. Inorg. Chem., 2004, 469.
  • [241] M. Olivan, O. Eisenstein, KG. Caulton, Organometallics, 1997, 16, 2227.
  • [242] T. Opstal, F. Verpoort, J. Mol. Catal. A: Chemical, 2003, 200, 49.
  • [243] H. Katayama, H. Urushima, F. Ozawa, J. Organomet. Chem., 2000, 606, 16.
  • [244] H. Katayama, F. Ozawa, Chem. Lett., 1998, 67.
  • [245] H. Katayama, T. T. Yoshida, F. Ozawa, J. Organomet. Chem., 1998, 562, 203.
  • [246] A.P. Contreras, A.M. Cerda, M.A. Tlenkopatchev, Macromoi. Chem. Phys., 2002, 203, 1811.
  • [247] I. del Rio, G. van Koten, Tetrahedron Lett., 1999, 40, 1401.
  • [248] H. Katayama, F. Yonezawa, M. Nagao, F. Ozawa, Macromolecules, 2002, 35, 1133.
  • [249] M. Saoud, A. Romerosa, M. Peruzzini, Organometallics, 2000, 19, 4005.
  • [250] J. Louie, R.H. Grubbs, Angew. Chem., Int. Ed., 2001,40,247.
  • [251] A. Fürstner, M. Picquet, C. Bruneau, P.H. Dixneuf, Chem. Commun., 1998, 1315.
  • [252] M. Picquet, D. Touchard, C. Bruneau, P.H. Dixneuf, New J. Chem., 1999, 141.
  • [253] A. Fürstner, M. Liebl, C.W. Lehmann, M. Picquet, R. Kunz, C. Bruneau. D. Touchard, P.H. Dixneuf, Chem. Eur. J., 2000, 6, 1847.
  • [254] M. Picquet, C. Bruneau, P.H. Dixneuf, Chem. Commun., 1998, 2249.
  • [255] R. Castarlenas, D. Semeril, A.F. Noels, A. Demonceau, P.H. Dixneuf, J. Organomet. Chem., 2002, 663, 235.
  • [256] S. Rigaut, D. Touchard, P.H. Dixneuf, Coord. Chem. Rev., 2004, 248, 1585.
  • [257] M. Bassetti, F. Centola, D. Semeril, C. Bruneau, P.H. Dixneuf, Organometallics, 2003, 22, 4459.
  • [258] R. Castarlenas, P.H. Dixneuf, Angew. Chem., Int. Ed., 2003, 42, 4524.
  • [259] L. Jafarpour, J. Huang, E.D. Stevens, S.P. Nolan, Organometallics, 1999, 18, 3760.
  • [260] H.-J. Schanz, L. Jafarpour, E.D. Stevens, S.P. Nolan, Organometallics, 1999, 18, 5187.
  • [261] A. Fiirstner, A.F. Hill, M. Liebl, J.D.E. Wilton-Ely, Chem. Commun., 1999, 601.
  • [262] K.J. Harlow; A.F. Hill, J.D.E.T. Wilton-Ely, J. Chem. Soc., Dalton Trans., 1999, 285.
  • [263] I.A. Abdallaoui, D. Semeril, P.H. Dixneuf, J. Mol. Catal. A: Chemical, 2002, 182-183, 577.
  • [264] R. Castarlenas, C. Fischmeister, C. Bruneau, P.H. Dixneuf, J. Mol. Catal A: Chemical, 2004, 213, 31.
  • [265] S.M. Hansen, F. Rominger, M. Metz, P. Hofmann, Chem. Eur. J., 1999, 5, 557.
  • [266] S.M. Hansen, M.A.O. Volland, F. Rominger, F. Eisentrager, P. Hofmann, Angew. Chem., Int. Ed., 1999, 38, 1273.
  • [267] M.A.O. Volland, B.F. Straub, I. Gruber, F. Rominger, P. Hofmann, J. Organomet. Chem. 2001, 617-618, 288.
  • [268] M.A.O. Volland, S.M. Hansen, F. Rominger, P. Hofmann, Organometallics, 2004, 23, 800.
  • [269] P. Hofmann, M.A.O. Volland, S.M. Hansen, F. Eisentrager, J.H. Gross, K. Stengel, J. Organomet. Chem., 2000, 606, 8 8.
  • [270] C. Adlhart, P. Chen, Intrinsic Reactivity of Ruthenium Carbenes, [w:] Handbook of Metathesis, R.H. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, Rozdział 1.10.
  • [271] W. Stüer, J. Wolf, H. Werner, P. Schwab, M. Schulz, Angew. Chem., Int. Ed., 1998, 37, 3421.
  • [272] A.H. Hoveyda, Catalytic Asymmetric Olefin Metathesis, [w:] Handbook of Metathesis, RH. Grubbs, Ed., Wiley-VCH, Weinheim, 2003, rozdz. 2.3.
  • [273] T.J. Seiders, D.W. Ward, RH. Grubbs, Org. Lett, 2001, 3, 3225.
  • [274] J.J. Van Veldhuizen, S.B. Garber, J.S. Kingsbury, A.H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 4954.
  • [275] J.J. Van Veldhuizen, D.G. Gillingham, S.B. Garber, A.H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 12502.
  • [276] D.G. Gillingham, O. Kataoka, S.B. Garber. A.H. Hoveyda, J. Am. Chem. Soc., 2004, 126, 12288.
  • [277] M.C. Perry, K. Burgess, Tetrahedron: Asymmetry, 2003, 14, 951.
  • [278] J.S. Kingsburry, A.H. Hoveyda, Polymer-supported Olefin metathesis Catalysts for Organic and Combinatorial Synthesis, [w:] Polymeric Materials in Organic Synthesis and Catalysis, M.R. Buchmeiser, Ed., Willey-VCH, Weinheim, 2003, rozdział 11.
  • [279] M. R. Buchmeiser, New J. Chem., 2004, 28, 549.
  • [280] P. Nieczypor, W. Buchowicz, W.J.N. Meester, F.P.J.T. Rutjes, J.C. Mol, Tetrahedron Lett., 2001, 42, 7103.
  • [281] J.O. Krause, S. Lubbad, M. Mayr, O. Nuyken, M.R. Buchmeiser, Polym. Prepr., 2003, 44, 790.
  • [282] J.O. Krause, S. Lubbad, O Nuyken, M.R. Buchmeiser, Adv. Synth. Catal., 2003, 345, 996.
  • [283] J.O. Krause, S.H. Lubbad, O. Nuyken, M.R. Buchmeiser, Macromol. Rapid Commun., 2003, 24, 875.
  • [284] S.T. Nguyen, R.H. Grubbs, J. Organomet. Chem., 1995, 497, 195.
  • [285] S.C. Schürer, S. Gessler, N. Buschmann, S. Blechert, Angew. Chem., Int. Ed., 2000, 39, 3898.
  • [286] S. Randl, N. Buschmann, S.J. Connon, S. Blechert, Synlett, 2001, 1547.
  • [287] M. Mayr, B. Mayr, M.R. Buchmeiser, Angew: Chem., Int. Ed., 2001, 40, 3839.
  • [288] M. Mayr, M.R. Buchmeiser, K. Wurst, Adv. Synth. Catal., 2002, 344, 712.
  • [289] M. Ahmed, A.G.M. Barrett, D.C. Braddock, S.M. Cramp, P.A. Procopiou, Tetrahedron Lett., 1999, 40, 8657.
  • [290] M. Ahmed, T. Amauld, A.G.M. Barrett, D.C. Braddock, P.A. Procopiou, Synlett, 2000, 1007.
  • [291] L. Jafarpour, S.P. Nolan, Org. Chem., 2000, 2, 4075.
  • [292] L. Jafarpour, M.-P. Heck, C. Baylon, H.M. Lee, C. Mioskowski, S.P. Nolan, Organometallics, 2022, 21, 671.
  • [293] S. Varray, R. Lazaro, J. Martinez, F. Lamaty, Organometallics, 2003. 22, 2426.
  • [294] A.G.M. Barrett, S.M. Cramp, R.S. Roberts, Org. Lett., 1999, 1, 1083.
  • [295] Q. Yao, Angew. Chem., Int. Ed., 2000, 39, 3896.
  • [296] Q. Yao, A.R. Motta, Tetrahedron Lett., 2004, 45, 2447.
  • [297] J. Dowden, J. Savovic, Chem. Commun., 2001, 37.
  • [298] J.S. Kingsbury, S.B. Garber, J.M. Giftos, B.L. Gray, M.M. Okamoto, R.A. Farrer, J.T. Fourkas, A.H. Hoveyda, Angew. Chem., Int. Ed., 2001, 40, 4251.
  • [299] S.J. Connon, A.M. Dunne, S. Blechert, Angew. Chem., Int. Ed., 2002, 41, 3835.
  • [300] Q. Yao, Y. Zhang, J. Am. Chem. Soc., 2004, 126, 74.
  • [301] R. Akiyama, S. Kobayashi, Angew. Chem., Int. Ed., 2002, 41, 2602.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS2-0007-0093
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.