N-Heterocyclic carbenes as highly efficient ancillary ligands in homogeneous and immobilized metathesis ruthenium catalytic systems

Dragutan, Ileana; Dragutan, Valerian; Delaude, Lionel; Demonceau, Albert

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Dragutan, Ileana; Dragutan, Valerian; Delaude, Lionel et al.

2005 • In ARKIVOC, (Part 10), p. 206-253

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Keywords :

N-Heterocyclic carbenes; ruthenium complexes; ring-closing metathesis; rotaxanes; natural products; acyclic diene metathesis

Abstract :

[en] This general overview focuses on novel N-heterocyclic carbene (NHC) Ru complexes, now at the forefront of research in metathesis chemistry, and on their derived multiple applications in targeted organic, polymeric and natural compound synthesis. This outstanding, large class of ruthenium precatalysts combines high activity and selectivity with increased stability and good tolerance towards organic functionalities, air and moisture. The NHC ancillary ligands allow manipulation of the catalytic performance through adjustment of electronic and steric parameters in the ruthenium coordination sphere, facilitate introduction of chiral motifs, and enable convenient immobilization of homogeneous initiators onto solid supports. A broad spectrum of practical applications is discussed.

Disciplines :

Chemistry

Author, co-author :

Dragutan, Ileana

Dragutan, Valerian

Delaude, Lionel ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique

Demonceau, Albert ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique

Language :

English

Title :

N-Heterocyclic carbenes as highly efficient ancillary ligands in homogeneous and immobilized metathesis ruthenium catalytic systems

Publication date :

2005

Journal title :

ARKIVOC

ISSN :

1551-7004

eISSN :

1551-7012

Publisher :

Arkat Usa Inc

Issue :

Part 10

Pages :

206-253

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 26 June 2009

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Bibliography

(a) Arduengo, A.J.; Harlow, R.L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
(b) Herrmann, W.A.; Kocher, C. Angew. Chem., Int. Ed. 1997, 36, 2162.
(c) Arduengo, A.J. Acc. Chem. Res. 1999, 32, 913.
(d) Herrmann, W.A. Angew. Chem., Int. Ed. 2002, 41, 1290.
For recent reviews, see: (a) Herrmann, W.A.; Kohl, F.J.; Schwartz, J. In Synthetic Methods of Organometallic and Inorganic Chemistry, Vol. 9, Herrmann W.A., Ed., Georg Thieme Verlag: Stuttgart, New York 2000.
(b) Bourissou, D.; Guerret, O.; Gabbai, F.P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
(c) Weskamp, T.; Bohm, V.P.W.; Herrmann, W.A. J. Organomet. Chem. 2000, 600, 12.
(d) Jafarpour, L.; Nolan, S.P. J. Organomet. Chem. 2001, 617-618, 17.
(e) Jafarpour, L.; Nolan, S.P. Adv. Organomet. Chem. 2001, 46, 181.
(f) Herrmann, W.A.; Weskamp, T.; Bohm, V.P.W. Adv. Organomet. Chem. 2002, 48, 1.
For selected references, see: (a) Arnold, P.L.; Scarisbrick, A.C.; Blake, A.J.; Wilson, C. Chem. Commun. 2001, 2340.
(b) Kovacevic, A.; Grundemann, S.; Miecznikowski, J.R.; Clot, E.; Eisenstein, O.; Crabtree, R.H. Chem. Commun. 2002, 2580.
(c) Carlson, R.G.; Gile, M.A.; Heppert, J.A.; Mason, M.H.; Powell, D.R.; Velde, D.V.; Vilain, J.M. J. Am. Chem. Soc. 2002, 124, 1580.
(d) Louie, J.; Gibby, J.E.; Farnworth, M. V.; Tekavek, T.N. J. Am. Chem. Soc. 2002, 124, 15188.
(e) Danopoulos, A.A.; Winston, S.; Motherwell, W.B. Chem. Commun. 2002, 1376.
(f) Dioumaev, V.K.; Bullock, R.M. Nature 2003, 424, 530.
(g) McGuinness, D.S.; Gibson, V.C.; Vass, D.F.; Steed, J.W. J. Am. Chem. Soc. 2003, 125, 12716.
(h) Hu, X; Castro-Rodriguez, L.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 12237.
(i) Diggle, R.A.; Macgregor, S.A.; Whittlesey, M.K. Organometallics 2004, 23, 1857.
(a) Peris, E.; Loch, J.A.; Mata, J.; Crabtree, R.H. Chem. Commun. 2001, 201.
(b) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S.P.; Mioskowski, C. Org. Lett. 2000, 2, 1517.
See also, (c) Herrmann, W.A. Ed. Synthetic Methods of Organometallic and Inorganic Chemistry, Vol. 9, Georg Thieme Verlag: Stuttgart, New York, 2000.
(a) Huang, J.; Stevens, E.D.; Nolan, S.P.; Petersen, J.L. J. Am. Chem. Soc. 1999, 121, 2674.
(b) Huang, J.; Schanz, H.-J.; Stevens, E.D.; Nolan, S.P. Organometallics 1999, 18, 2370.
(c) Hillier, A.C.; Sommer, W.J.; Yong, B.S.; Petersen, J.L.; Cavallo, L.; Nolan, S.P. Organometallics 2003, 22, 4322.
(a) Lee, H.M.; Smith, D.C.; He, Z.Jr.; Stevens, E.D.; Yi, C.S.; Nolan, S.P. Organometallics 2001, 20, 794.
(b) Vasquez-Serrano, L.D.; Owens, B.T.; Buriak, J.M. Chem. Commun. 2002, 2518.
(c) Dharmasena, U.L.; Foucault, H.M.; dos Santos, E.N.; Fogg, D.E.; Nolan, S.P. Organometallics 2005, 24, 1056.
See also, (d) Genet, J.P. Acc. Chem. Res. 2003, 36, 908.
(a) Hillier, A.C.; Lee, H.M.; Stevens, E.D.; Nolan, S.P. Organometallics 2001, 20, 4246.
(b) Albrecht, M.; Miecznikowski, J.R.; Samuel, A.; Faller, J.F.; Crabtree, R.H. Organometallics 2002, 21, 3596.
(c) Miecznikowski, J.R.; Crabtree, R.H. Organometallics 2004, 23, 629.
(d) Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics 2004, 23, 1490.
(e) Burling, S.; Wittlessey, M.K.; Williams, J.M.J. Adv. Synth. Catal. 2005, 347, 591.
Herrmann, W.A.; Elison, M.; Fischer, J.; Kocher, C. U.S. Patent 5,663,451, 1997.
Kaur, H.; Zinn, F.K.; Stevens, E.D.; Nolan, S.P. Organometallics 2004, 23, 1157.
(a) Sutton, A.E.; Seigal, B.A.; Finegan, D.F.; Snapper, M.L. J. Am. Chem. Soc. 2002, 124, 13390.
(b) Baran, J.; Bogdanska, I.; Jan, D.; Delaude, L.; Demonceau, A.; Noels, A.F.; J. Mol. Catal. A: Chem. 2003, 190, 109.
(a) Schmidt, B. Eur. J. Org. Chem. 2003, 816.
(b) Schmidt, B. Chem. Commun. 2003, 1656. See also, Ref. 6c.
Viciu, M.S.; Zinn, F.K.; Stevens, E.D.; Nolan, S.P. Organometallics 2003, 22, 3175.
(a) Richel, A.; Delfosse, S.; Cremasco, C.; Delaude, L.; Demonceau, A.; Noels, A.F. Tetrahedron Lett. 2003, 44, 6011.
(b) Opstal, T.; Verpoort, F. Tetrahedron Lett. 2002, 43, 9259.
(c) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11.
(a) Gibson, S.E.; Johnstone, C.; Loch, J.A.; Steed, J.W.; Stevenazzi, A. Organometallics 2003, 22, 5374.
(b) Poulton, A.M.; Christie, S.D.R.; Fryatt, R.; Dale, S.H.; Elsegood, M.R.J.; Andrews, D.M. Synlett 2004, 2013.
For recent reviews, see: (a) Buchmeiser, M. Chem. Rev. 2000, 100, 1565.
(b) Dragutan, V.; Dragutan, I.; Balaban, A.T. Platinum Metals Rev. 2000, 44, 58.
(c) Dragutan, V.; Dragutan, I.; Balaban, A.T. Platinum Metals Rev. 2001, 45, pp.155.
(d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
(e) Trnka, T.M.; Grubbs, R.H. Acc. Chem. Res. 2001, 34, 18.
(f) Grubbs, R.H. Handbook of Metathesis, 2003, Vol. I, Wiley-VCH: Weinheim, Germany.
(g) C.S. Poulsen, C.S.; R. Madsen, R. Synthesis 2003, 1.
(h) Diver, S.T.; Giessert, A.J. Chem. Rev. 2004, 104, 1317.
See also, (i) Mohapatra, D.M.; Durugkar, K.A. ARKIVOC 2004, (i), 146.
(h) Dragutan, I.; Dragutan, V.; Filip, P. ARKIVOC 2005, (x), 105.
(a) Herrmann, W.A.; Elison, M.; Fischer, J.; Kocher, C.; Artus, G.R.J. Angew. Chem., Int. Ed. 1995, 34, 2371.
(b) Herrmann, W.A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93.
(c) McGuinness, D.S.; Green, M.J.; Cavell, K.J.; Skelton, B.W.; White, A.H. J. Organomet. Chem. 1998, 565, 165.
(d) Huang, J.; Grasa, G.; Nolan, S.P. Org. Lett. 1999, 1, 1307.
(e) Weskamp, T.; Bohm, V.P.W.; Herrmann, W.A. J. Organomet. Chem. 1999, 585, 348.
(f) Zhang, C.; Huang, J.; Trudell, M.L.; Nolan, S.P. J. Org. Chem. 1999, 64, 3804.
(g) Huang, J.; Nolan, S.P. J. Am. Chem. Soc. 1999, 121, 9889.
(h) Lee, H.M.; Nolan, S.P. Org. Lett. 2000, 2, 2053.
(i) Bohm, V.P.W.; Gstottmayr, C.W.K.; Weskamp, T.; Herrmann, W.A. J. Organomet. Chem. 2000, 595, 186.
(j) Schwartz, J.; Bohm, V.P.W.;Gardiner, M.G.; Grosche, M.; Herrmann, W.A.; Hieringer, W.S.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773.
(k) Tulloch, A.A.D.; Danopoulos, A.A.; Tooze, R.P.; Cafferkey, S.M.; Kleinhenz, S.; Hursthouse, M.B. Chem. Commun. 2000, 1247.
(l) McGuinness, D.S.; Cavell, K.J. Organometallics 2000, 19, 741.
(a) Peris, E.; Loch, J.A.; Mata, J.; Crabtree, R.H. Chem. Commun. 2001, 201.
(b) Yang, C.; Lee, H.M.; Nolan, S.P. Org. Lett. 2001, 3, 1511.
(c) Herrmann, W.A.; Bohm, V.P.W.; Gstottmayr, C.W.K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2001, 617-618, 616.
(d) Furstner, A.; Letner, A. Synlett 2001, 2, 290.
(e) Whitcombe, N.J.; Hii, K.K.; Gibson, S.E. Tetrahedron 2001, 57, 7449.
(f) Grundemann, S.; Albrecht, M.; Loch, J.A.; Faller, J.V.; Crabtree, R.H. Organometallics 2001, 20, 5485.
(g) Magill, A.M.; McGuiness, D.S.; Cavell, K.J.; Britovsek, G.J.P.; Gibson, V.C.; White, A.J.P.; Williams, D.J.; White, A.H.; Skelton, B.W. J. Organomet. Chem. 2001, 617-618, 546.
(h) Tulloch, A.A.D.; Danopoulos, A.A.; Tiezzard, G.J.; Coles, S.J.; Hursthouse, M.B.; Hay-Motherwell, R.S.; Motherwell, W.B. Chem. Commun. 2001, 1270.
(a) Grasa, G.A.; Viciu, M.S.; Huang, J.; Zhang, C.; Trudell, M.L.; Nolan, S.P. Organometallics 2002, 21, 2866.
(b) Hillier, A.C.; Grasa, G.A.; Viciu, M.S.;Lee, H.M.; Yang, C.; Nolan, S.P. J. Organomet. Chem. 2002, 653, 69.
(c) Gstottmayr, C.W.K.; Bohm, V.P.W.; Herdtweck, E.; Grosche, M.; Herrmann, W.A. Angew. Chem. Int. Ed. 2002, 41, 1363.
(d) Littke, A.F.; Fu, G.C. Angew. Chem. Int. Ed. 2002, 41, 4176.
(e) Kothia, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
(f) Selvakumov, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031.
(g) Herrmann, W.A.; Ofele, K.; von Preysing, D.; Schneider, S.K. J. Organomet. Chem. 2003, 687, 229.
(h) Altenhoff, G.; Goddard, R.; Lehmann, C.W.; Glorius, F. Angew. Chem., Int. Ed. 2003, 42, 3690.
(i) Eckhardt, M.; Fu, G.C. J. Am. Chem. Soc. 2003, 125, 13642.
(j) Lebel, H.; Janes, M.K.; Charette, A.B.; Nolan, S.P. J. Am. Chem. Soc. 2004, 126, 5046.
For comprehensive reviews, see: (a) Schrock, R.R.; Hoveyda, A.H. Angew. Chem., Int. Ed. 2003, 42, 4592.
(b) Grubbs, R.H. Ed.. Handbook of Metathesis, Vol. II-III Wiley-VCH: Weinheim, Germany 2003.
(c) Furstner, A. In Glycomimetics: Modern Synthetic Methodologies Roy, R., Ed., ACS Symp. Ser., Vol. 896, American Chemical Society: Washington 2005, 1.
(d) Dragutan, V.; Dragutan, I.; Balaban, A.T. Platinum Metals Rev. 2000, 44, 112.
(e) Dragutan, V.; Dragutan, I.; Balaban, A.T. Platinum Metals Rev. 2000, 44, 168.
(f) Dragutan, V.; Streck, R. "Catalytic Ploymerization of Cycloolefins" 2000, Elsevier: Amsterdam, The Netherlands.
(g) Imamoglu, Y.; Bencze, L. Eds. Novel Metathesis Chemistry: Well-defined Initiator Systems for Speciality Chemical Synthesis, Tailored Polymers and Advanced Material Applications, Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003.
(h) Dixneuf, P.H.; Bruneau, C. (Eds.). Ruthenium Catalysts and Fine Chemistry, Springer-Berlin 2004.
Topics Organomet. Chem. 2004, Vol. 11.
(a) S.J. Connon, S.J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
(b) Chatterjee, A.K.; Choi, T.-L.; D.P. Sanders, D.P.; Grubbs, R.H. J. Am. Chem. Soc. 2003, 125, 11360.
(c) Furstner, A.; Jeanjean, F.; Razon, P.; Wirtz, C.; Mynott, R. Chem. Eur. J. 2003, 9, 320.
(d) Mohapatra, D.M.; Yellol, G.S. ARKIVOC 2003 (ix) 21.
(e) Furstner, A.; Castanet, A.S.; Radkowski, K.; Lehmann, C.W. J. Org. Chem. 2003, 68, 1521.
(a) Herrmann W.A. Ed. Synthetic Methods of Organometallic and Inorganic Chemistry, Vol. 1, Georg Thieme Verlag, Stuttgart, New York, 1995.
(b) Hitchcock, P.B.; Lappert, M.F.; Terrenos, P.; Wainwright, K.P. J. Chem. Soc., Chemm. Commun. 1980, 1180.
(a) Arduengo, A.J.; Krafczyk, R.; Schmutzler, R.; Craig, H.A.; Goerlich, J.R.; W.J. Marshall, W.J.; Unverzagt, M. Tetrahedron, 1999, 55, 14523.
(b) Arduengo, A.J.;Davidson, F.; Dias, H.V.R.; Goerlich, J.R.; Khasnis, D.; Marshall, W.J. J. Am. Chem. Soc. 1997, 119, 12742.
(c) Arduengo, A.J.; Goerlich, J.R.; Marshall, W.J. J. Am. Chem. Soc. 1996, 117, 11027.
(d) Arduengo, A.J.; Dias, H.V.R.; Harlow, R.L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
(e) Arduengo, A.J.; Dias, H.V.R.; Kline, M. J. Am. Chem. Soc. 1992, 114, 9724.
Wanzlick, V.H.W.; Schonher, H.-J. Angew. Chem. 1968, 80, 154.
(a) Yang, L.; Mayr, M.; Wurst, K.; Buchmeiser, M.R. Chem. Eur. J. 2004, 10, 5761.
(b) G. Altenhoff, G.; Goddard, R.; Lehmann, C.; Glorius, F. Angew. Chem., Int. Ed. 2003, 115, 3818.
(c) G. Altenhoff, G.; Goddard, R.; Lehmann, C.; Glorius, J. Am. Chem. Soc. 2004, 126, 15195.
(d) F. Glorius, G. Altenhoff, G.; Goddard, R.; Lehmann, C. Chem. Commun. 2002, 2704.
(a) Herrmann, W.A.; Kocher, C.; Goossen, L.J.; Artus, G.R. Chem. Eur. J. 1996, 2, 1627.
(b) Herrmann, W.A.; Goossen, L.J.; Spiegler, M. Organometallics 1998, 17, 2162.
(a) Perry, M.C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951.
(b) Powell, M.T.; Hou, D.-R.; Perry, M.C.; Cui, X.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 8878.
(c) Clyne, D.S.; Jin, J.; Genest, E.; Galluci, J.C.; Rajanbabu, T.V. Org. Lett. 2000, 2, 1125.
Schurer, S.C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem., Int. Ed. 2000, 39, 3898.
(b) Connon, S.J.; Dunne, A.M.; Blechert, S. Angew. Chem. 2002, 114, 3989.
Angew. Chem., Int. Ed. 2002, 41, 3835.
(a) Herrmann, W.A. Ed. Synthetic Methods of Organometallic and Inorganic Chemistry, Vol. 9, Georg Thieme Verlag, Stuttgart, New York 2000.
(b)Weskamp, T.; Bohm, V.P.W.; Herrmann, W.A. J. Organomet. Chem. 2000, 600, 12.
(c) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-618, 70.
(d) Furstner, A.; Seidel, G.; Kremzow, D.; Lehmann, C.W. Organometallics 2003, 22, 907.
Taton, T.A. ; Chen. P. Angew. Chem., Int. Ed. 1996, 35, 1011.
Liu, Y.; Lindner, P.E.; Lemal, D.M. J. Am. Chem. Soc. 1999, 121, 10626.
Huang, J.; Jafarpour, L.; Hillier, A.C.; Stevens, E.D.; Nolan, S.P. Organometallics 2001, 20, 2878.
Green, J.C.; Scurr, R.G.; Arnold, P.L.; Cloke, F.G.N. Chem. Commun. 1997, 1963.
(a) Weskamp, T.; Schattenmann, W.; Spiegler, M.; Herrmann, W.A. Angew. Chem. 1998, 110, 2631.
(b) Weskamp, T.; Kohl, F.J.; Hieringer, W.; Gleich, D.; Herrmann, W.A. Angew. Chem. 1999, 111, 2573.
(c). Weskamp, T.; Kohl, F.J.; Hieringer, W.; Gleich, D.; Herrmann, W.A. Angew. Chem. Int. Ed. 1999, 38, 2416.
Scholl, M.; Trnka, T.M.; Morgan, J.P.; Grubbs, R.H. Tetrahedron Lett. 1999, 40, 2247.
J. Huang, E.D. Stevens, S.P. Nolan and J.L. Petersen, J. Am. Chem. Soc. 1999, 121, 2674.
Schanz, H.J.; Jafarpour, L.; Stevens, E.D.; Nolan, S.P. Organometallics 1999, 18, 5187.
Louie, J.; Grubbs, R.H. Angew. Chem. Int. Ed. 2001, 40, 247.
Harlow, K.J.; Hill, A.H,; Wilton-Ely, J.D.E.T. J. Chem. Soc., Dalton Trans. 1999, 285.
Jafarpour, L.; Schanz, H.J.; Stevens, E.D.; Nolan, S.P. Organometallics 1999, 18, 5416.
Garber, S.B.; Kingsbury, J.S.; Gray, B.L.; Hoveyda, A.H. J. Am. Chem. Soc. 2000, 122, 8168.
Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 832;
Angew. Chem., Int. Ed. 2002, 41, 794.
Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem. 2002, 114, 4210;
Angew. Chem. Int. Ed. 2002, 41, 4038.
(a) H. Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509;
Angew. Chem., Int. Ed. 2002, 41, 4038.
(b) Dunne, A.M.; Mix, S.; Blechert, S. Tetrahedron Lett. 2003, 44, 2733.
Zaja, M.; Connon, S.J.; Dunne, A.M.; Rivard, M.; Buschmann, N.; Jiricek, J.; Blechert, S. Tetrahedron 2003, 59, 6545.
Love, J.A.; Morgan, J.P.; Trnka, T.M.; Grubbs, R.H. Angew. Chem. Int. Ed. 2002, 41, 4035.
Ung, T.; Hejl, A.; Grubbs, R.H.; Schrodi, Y. Organometallics 2004, 23, 5399.
De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11.
De Clercq, B.; Verpoort, F. Terahedron Lett. 2002, 43, 9101.
(a) Simal, F.; Delaude, L.; Jan, D.; Demonceau, A.; Noels, A.F. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1999, 40, 226.
(b) Delaude, L.; Demonceau, A.; Noels, A.F. In Ruthenium Catalysts and Fine Chemistry,
Dixneuf, P.H.; Bruneau, C. Eds. Topics Organomet. Chem. 2004, 11, 155.
Furstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C.W.; Mynott, R.; Stelzer, F.; Thiel, O.R. Chem. Eur. J. 2001, 7, 3236.
Scholl, M.; Ding, S.; Lee, C.W.; Grubbs, R.H. Org. Lett. 1999, 1, 953.
Seiders, T.J.; Ward, D.W.; Grubbs, R.H. Org. Lett. 2001, 3, 3225.
Van Veldhuizen, J.J.; Garber,S.B.; Kingsbury, J.S.; Hoveyda, A.H. J. Am. Chem. Soc. 2002, 124, 4954.
Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F.J.; Herrmann, W.A. Tetrahedron Lett. 1999, 40, 4787.
Weskamp, T.; Kohl, F.J.; Herrmann, W.A. J. Organomet. Chem. 1999, 582, 362.
(a) Frenzel, U.; Weskamp, T.; Kohl, F.J.; Schattenmann, W.C.; Nuyken, O.; Herrmann, W.A. J. Organomet. Chem. 1999, 586, 263.
(b) Herrmann, W.A.; Schattenmann, W.C.; Weskamp, T. German Patent Appl. 19,815,275.2, 1998.
(a) E.R. Hartley, Catalysis by Metal Complexes, Supported Metal Reagents, Reidel: Dordrecht, 1984.
(b) A.J. Sandee, L.A. Van Der Veen, J.N.H. Reek, P.C.J. Kamer, M. Lutz, A.L. Spek and P.W.N.M. Van Leeuwen, Angew. Chem., Int. Ed. 1999, 38, 3231.
(c) M.K. Dalal, M.J. Upadhyay and R.N. Ram, J. Mol. Catal. A : Chem. 1999, 142, 325.
(d) H.C.L. Abbenhuis, Angew. Chem., Int. Ed. 1999, 38, 1058.
(e) C.-J. Liu, W.-Y. Yu, S.-G. Li and C.-M. Che, J. Org. Chem. 1998, 63, 7364.
(a) Yao, Q.W. Angew. Chem., Int. Ed. 2000, 39, 3896.
(b) A. Heckel,A.; Seebach, D. Angew. Chem., Int. Ed. 2000, 39, 1.
(c) Dowden, J.; Savovic, Chem. Commun. 2001, 37.
(d) Gibson, S.E.; Swamy, V.M. Adv. Synth. Catal. 2002, 344, 619.
(e) Mayr, M.; Buchmeiser, M.R.; Wurst, K. Adv. Synth. Catal. 2002, 344, 712.
(a) Jafarpour, L.; Heck, M.P.; Baylon, C.; Lee, H.L.; Mioskowski, C.; Nolan, S.P. Organometallics 2002, 21, 671.
(b) Connon, S.J.; Dunne, A.M.; Blechert, S. Angew. Chem. 2002, 41, 3989.
Angew. Chem., Int. Ed. 2002, 41, 3835.
(c) Cannon S.J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002, 12, 1873.
(d) Krause, J.O.; Nuyken, O.; Wurst, K.; Buchmeiser, M.R. Chem. Eur. J. 2004, 10, 777.
(a) Clark, J.H.; Macquarrie, D.J. Org. Proc. Res. Develop.1997, 1, 149;
(b) Ernst, S.; Gläser, R.; Selle, M. Stud. Surf. Sci. Catal. 1997, 105, 1021.
(c) Clark, J.H.; Macquarrie, D.J. Chem. Soc. Rev. 1996, 25, 303.
(d) Garber, S.B.; Kingsbury, J.S.; Gray, B.L.; Hoveyda, A.H. J. Am. Chem. Soc. 2000, 122, 8168.
(e) Hultzisch, K.C.; Jernelius, J.A.; Hoveyda, A.H.; Schrock, R.R. Angew. Chem., Int. Ed. 2002, 41, 589.
(a) Ahmed, M.; Arnauld, T.; Barrett, A.G.M.; Braddock, D.C.; Procopiou, A. Synlett 2000, 9, 1007.
(b) Jafarpour L.; Nolan, S.P. Org. Lett. 2000, 2, 4075.
Connon, S.J.; Dunne, A.M.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 3835.
Kingsbury, J.S.; Garber, S.B.; Giftos, J.M.; Gray, B.L.; Okamoto, M.M.; Farrer, R.A.; Fourkas, J.T.; Hoveyda, A.M. Angew. Chem., Int. Ed. 2001, 40, 4251.
(a) Mayr, M.; Wang, D.; Kroll, R.; Schuler, N.; Pruhs, S.; Furstner, A.; Buchmeiser, M.R. Adv. Synth. Catal. 2005, 347, 484.
(b) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
(a) Schaverien, C.J.; Schrock, R.R.; Dewan, J.C. J. Am. Chem. Soc. 1986, 108, 2771.
(b) Schrock, R.R.; DePue, D.T.; Feldman, J.; Schaverien, C.J.; Dewan, J.C.; Liu, A.H. J. Am. Chem. Soc. 1987, 109, 1423.
Furstner, A.; Thiel, O.R.; Ackermann, L.; Schanz, H.-J.; Nolan, S.P. J. Org. Chem. 2000, 65, 2204.
(a) Rutjes, F.P.J.T.; Schoemaker, H.E. Tetrahedron Lett. 1997, 38, 677.
(b) Nicolaou, K.C.; Rodriguez, R.N.; Mitchell, H.J.; van Delft, F.L. Angew. Chem. 1998, 110, 1975.
(c) Krikstolaityte, S.; Hammer, K.; Undheim, K. Tetrahedron Lett. 1998, 39, 7595.
(d) Stuer, W.; Wolf, J.; Werner, H.; Schwab, P.; Schulz, M. Angew. Chem. 1998, 110, 3603.
(e) Grossmith, C.E.; Senia, F.; Wagner, J. Synlett 1999, 1660.
(a) Ghosh, A.K.; Hussain, K.A. Tetrahedron Lett. 1998, 39, 1881.
(b) Ghosh, A.K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
(c) Ghosh, A.K.; Liu, C. Chem. Commun. 1999, 1743.
(d) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187.
(e) Wipf, P.; Weiner, W.S. J. Org. Chem. 1999, 64, 5321.
(f) Dirat, O.; Kouklovsky, C.; Langlois, Y.; Lesot, P.; Courtieu, J. Tetrahedron Asymmetry 1999, 10, 3197.
(a) Selected references, see: Mori, M. Top. Organomet. Chem. 1998, 1, 133.
(b) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
(c) Mori, M.; Kiamura, T.; Sakakibara, N.; Sato, I. Org. Lett. 2000, 2, 543.
(d) Smulik, J.A.; Diver, S.T. J. Org. Chem. 2000, 65, 1788.
(e) Diver, S.T. Chem. Rev. 2004, 104. 1317.
See also, Katz, T.J.; Sivavec, T.M. J. Am. Chem. Soc. 1985, 107, 737.
Michrowska, A.; Wawrzyniak, P.; Grela, K. Eur. J. Chem. 2004, 2053.
Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 6425.
(a) Amabilina, D.B.; Stoddart, J.F. Chem. Rev. 1995, 95, 2725.
(b) Sauvage, J.-P.; Dietrich-Buchecker, Eds. Molecular Catenanes, Rotaxanes and Knots, Wiley-VCH: Weinheim 1999.
See also, Dragutan, V.; Balaban, A.T.; Dimonie, M. Olefin Metathesis and Ring-Opening Polymerization of Cycloolefins, Wiley: Chichester, New York 1985.
(a) Weck, M.; Mohr, B.; Sauvage, J.-P.; Grubbs, R.H. J. Org. Chem. 1999, 64, 5463.
(b) Kidd, T.J.; Leigh, D.A.; Wilson, A.J. J. Am. Chem. Soc. 1999, 121 1599.
Wisner, J.A.; Beer, P.D.; Drew, M.G.B.; Sambrook, M.R. J. Am. Chem. Soc. 2002, 124, 12469.
(a) Cantrill, S.J.; Pease, A.R.; Stoddart, J.F. J. Chem. Soc. Dalton Trans. 2000, 3715.
(b) Cantrill, S.J.; Fulton, D.A.; Heiss, A.M.; Pease, A.R.; Stoddart, White, A.J.P.; Williams, D.J. Chem. Eur. J. 2000, 6, 2274.
Kilbinger, A.F.M.; Cantrill, S.J.; Waltman, A.W.; Day, M.W.; Grubbs, R.H. Angew. Chem., Int. Ed. 2003, 42, 3281.
Martinez, V.; Blais, J.-C.; Astruc, D. Angew. Chem., Int. Ed. 2003, 42, 4366.
Ackermann, L.; Tom, D.E.; Furstner, A. Tetrahedron 2000, 56, 2195.
Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693.
(a) Park, S.H.; Kang, H.K.; Ko, S.; Park, S.; Chang, S. Tetrahedorn Asymmerty 2001, 12, 2621.
(b) Lim, S.H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056.
(a) Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469.
(b) Neipp, C.E.; Martin, S.F. Tetrahedron Lett. 2002, 43, 1779.
(a) Smith III, A.B.; Kozmin, S.A.; Adams, C.M.; Paone, D.V. J. Am. Chem. Soc. 2000, 122, 4984.
(b) Smith III, A.B.; Adams, C.M.; Kozmin, S.A. J. Am. Chem. Soc. 2001, 123, 990.
Furstner, A.; Aissa, C.; Riveiros, R.; Ragot, J. Angew. Chem., Int. Ed. 2002, 41, 4763.
Nicolaou, C.K.; Vassilikogiannakis, G.; Montagnon, T. Angew. Chem., Int. Ed. 2002, 41, 3276.
Couladouros, E.A.; Mihou, A.P.; Bouzas, E.A. Org. Lett. 2004, 6, 977.
Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020.
Chen, J.; Forsyth, C.J. Angew. Chem., Int. Ed. 2004, 43, 2148.
Kim, D.; Lee, J.; Shim, P.J.; Lim, J.I.; Doi, T.; Kim, S. J. Org. Chem. 2002, 67, 772.
Sun, J.; Sinha, S.C. Angew. Chem., Int. Ed. 2002, 41, 1381.
Furstenr A.; Thiel, O.R.; Kindler, N.; Bartkwoska, B. J. Org. Chem. 2000, 65, 7990.
Garbaccio, R.M.; Stachel, S.J.; Baeschlin, D.K.; Danishefsky, S.J. J. Am. Chem. Soc. 2001, 123, 10903.
(a) Furstner, A.; Thiel, O.R.; Blanda, G. Org. Lett. 2000, 2, 3721.
(b) Furstner, A.; Dirkes, T.; Thiel, O.R.; Blanda, G Chem. Eur. J. 2001, 7, 5286.
(c) Snider, B.B.; Song, F. Org. Lett. 2001, 3, 1817.
(d) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J.K. J. Am. Chem. Soc. 2002, 124, 3245.
Banwell, M.; McRae, K.J. Org. Lett. 2000, 2, 3583.
Dvorak, C.A.; Schmitz, W.D.; Poon, D.J.; Pryde, D.C.; Lawson, J.P.; Amos, R.A.; Meyers, A.I. Angew. Chem., Int. Ed. 2000, 39, 1664.
Weskamp, T.; Schattenmann, W.C.; Spiegler, M.; Herrmann, W.A. Angew. Chem., Int. Ed. 1998, 37, 2490.
Frenzel, U.; Weskamp, T.; Kohl, F.J.; Schattenmann, W.C.; Nuyken, O.; Herrmann, W.A. J. Organomet. Chem. 1999, 586, 263.
(a) Bielawski, C.W.; Grubbs, R.H. Angew. Chem., Int. Ed. 2000, 39, 2903.
(b) Delaude, L.; Demonceau, A.; Noels, A.F. Chem. Commun. 2001, 986.
(c) Delaude, L.; Szypa, M.; Demonceau, A.; Noels, A.F. Adv. Synth. Catal. 2002, 344, 749.
(a) Bielawski, C.W.; Benitez, D.; Grubbs, R.H. Science 2002, 297, 2041.
(b) Bielawski, C.W.; Benitez, D.; Grubbs, R.H. J. Am. Chem. Soc. 2003, 125, 8424.
(a) Wagener, K.B.; Boncella, J.M. Makromol. Chem. 1990, 191, 365.
(b) Wagener, K.B.; Nel, J.C.; Konzelman, J.; Boncella, J.M. Macromolecules 1990, 23, 5155.
(c) Smith, J.A.; Brzezinska, K.R.; Valenti, D.J.; Wagener, K.B. Macromolecules 2000, 33, 3781.
(d) Schwendeman, J.E.; Church, A.C.; Wagener, K.B. Adv. Synth. Catal. 2002, 344, 587.
(a) Hopkins, T.E.; Pawlow, J.H.; Tep. F.; Wagener, K.B. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 2002, 43, 281.
(b) Hopkins, T.E.; Wagener, K.B. Adv. Mater. 2002, 14, 1703.
(c) Hopkins, T.E.; Wagener, K.B. Macromolecules 2003, 36, 2206.
(d) Hopkins, T.E.; Wagener, K.B. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 2003, 44, 985.
Hopkins, T.E.; Wagener, K.B. Macromolecules 2004, 37, 1180.
(a) Matyjaszewski, K. Chem. Eur. J. 1999, 5, 3095.
(b) Kamigaito, M.; T. Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101 3689.
(c) M. Sawamoto, M.; Kamigaito, M. Chemtech 1999, 29, 30.
(a) Simal. F.; Demonceau, A.; Noels, Angew. Chem., Int. Ed. 1999, 38, 538.
(b) A.F. Simal, F.; Jan, D.; Delaude, L.; Demonceau, A.; Soirlet, M.-R.; Noels, A.F. Can. J. Chem. 2001, 79, 529.
(c) Demonceau, A.; Simal, F.; Delaude, L.; Noels, A.F. 13th International Symposium on Olefin Metathesis and Related Chemistry, Rolduc, Kerkade, The Netherlands, July, 1999.
(a) Amir-Ebrahimi, V.; Hamilton, J.C.; Nelson, J.; Rooney, J.J. Chem. Commun. 1999, 1621.
(b) Amir-Ebrahimi, V.; Hamilton, J.C.; Nelson, J.; Rooney, J.J. In ROMP and Related Chemistry: State of the Art and Visions for the New Century, Khosravi, E.;Szymanska-Buzar, T., Eds., NATO Advanced Study Institute (ASI), Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002, p 217.
(a) Demonceau, A.; Simal, F.; Noels, A.F. In ROMP and Related Chemistry: State of the Art and Visions for the New Century, Khosravi, E.; Szymanska-Buzar, T., Eds., NATO Advanced Study Institute (ASI), Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002, p 227.
(b) Delaude, L.; Delfosse, S.; Richel, A.; Demonceau, A.; Noels, A.F. Chem. Commun. 2003, 1526.
(a) Simal, F.; Delfosse, S.; A. Demonceau, Noels, A.F.; Denk, K.; Kohl, F.J.; Weskamp, T.; Herrmann, W.A. Chem. Eur. J. 2002. 8, 3047.
(b) Opstal, T.; Verpoort, F. New. J. Chem. 2003, 27, 257.