Abstract
The article contains sections titled:
1. |
Definition |
2. |
History |
3. |
Mechanistic Fundamentals |
3.1. |
Ligands |
3.2. |
Changes in Oxidation State |
3.3. |
Changes in Coordination Number and Coordination Geometry |
3.4. |
Catalytic Elementary Steps |
4. |
Metals and Ligands in Homogeneous Catalysis |
4.1. |
Transition Metals |
4.2. |
Ligand Properties |
4.2.1. |
Ligand Basicity |
4.2.2. |
Steric Demand of Ligands |
4.2.3. |
Asymmetric Ligands |
5. |
Important Industrial Applications |
5.1. |
Hydroformylation |
5.2. |
Carbonylation |
5.3. |
Oligomerization |
5.3.1. |
Oligomerization of Alkenes |
5.3.2. |
Oligomerization of 1,3-Dienes |
5.3.3. |
Oligomerization of Alkynes |
5.3.4. |
Co-oligomerization |
5.4. |
Telomerization |
5.5. |
Polymerization |
5.6. |
Hydrocyanation |
5.7. |
Coupling Reactions with Aromatics |
5.8. |
Metathesis |
5.9. |
Hydrogenation |
5.10. |
Oxidation |
5.11. |
Amination and Hydroamination |
5.12. |
Isomerization |
References
- 1 A. Behr: Angewandte homogene Katalyse, Wiley-VCH, Weinheim 2008.
- 2 S.M. Roberts, J. Xiao, T. Pickett, J. Whittall: Catalysts for Fine Chemical Synthesis, vol. 3, Wiley-VCH, Weinheim 2004.
- 3 M. Beller, C. Bolm (eds.): Transition Metals for Organic Synthesis, 2nd ed., Wiley-VCH, Weinheim 2004.
- 4
P.W.N.M. van Leeuwen:
Homogeneous Catalysis — Understanding the Art,
Kluwer Academic Publishing,
Dordrecht
2004.
10.1007/1-4020-2000-7 Google Scholar
- 5 I.T. Horváth: Encyclopedia of Catalysis, Wiley-VCH, Weinheim 2003.
- 6 B. Cornils, W.A. Herrmann, R. Schlögl, C.-H. Wong: Catalysis from A to Z–A Concise Encyclopedia, 2nd ed., Wiley-VCH, Weinheim 2003.
- 7
B. Cornils,
W.A. Herrmann (eds.):
Applied Homogeneous Catalysis with Organometallic Compounds,
2nd ed.,
vols. 1–3,
Wiley-VCH,
Weinheim
2002.
10.1002/9783527618231 Google Scholar
- 8 M.E. Ford: Catalysis of Organic Reactions, Marcel Dekker, New York 2001.
- 9 J. Tsuji: Transition Metal Reagents and Catalysis — Innovations in Organic Synthesis, John Wiley & Sons, Chichester 2000.
- 10 R. Bates: Organic Synthesis Using Transition Metals, Sheffield Academic Press, 2000.
- 11
S. Bhaduri,
D. Mukesh:
Homogeneous Catalysis — Mechanisms and Industrial Applications,
Wiley-Interscience,
New York
2000.
10.1002/0471220388 Google Scholar
- 12 L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse: Application of Transition Metal Catalysis in Organic Synthesis, Springer-Verlag, Heidelberg 1998.
- 13 G.W. Parshall, S.D. Ittel: Homogeneous Catalysis, 2nd ed., Wiley, New York 1992.
- 14 Topics in Organometallic Chemistry, Springer-Verlag, Berlin.
- 15 P.W.N.M. Leeuwen, B.R. James (eds.): Catalysis by Metal Complexes, vols. 1–28, Springer-Verlag, Heidelberg 1976–2005.
- 16 M. Röper: “Homogene Katalyse in der Chemischen Industrie”, Chem. Unserer Zeit 40 (2006) 126.
- 17 P.T. Anastas, M. Kirchhoff, T.C. Williamson: “Catalysis as a Foundational Pillar of Green Chemistry”, Appl. Catal. A 221 (2001) 3–13.
- 18 B. Lindström, L.J. Petterson: “A brief history of catalysis”, CATTECH 7 (2003) no. 4, 130–138.
- 19 S. Neufeld: Chronologie Chemie–Entdecker und Entdeckungen, 3rd ed., Wiley-VCH, Weinheim 2003.
- 20
B. Heaton:
Mechanisms in Homogeneous Catalysis,
Wiley-VCH,
Weinheim
2005.
10.1002/3527605134 Google Scholar
- 21
Ch. Elschenbroich:
Organometallchemie,
5th ed.,
Teubner,
Stuttgart
2005.
10.1007/978-3-322-99958-0 Google Scholar
- 22
R.B. Grossmann:
The Art of Writing Reasonable Organic Reaction Mechanisms,
Springer-Verlag,
New York
1999, chap. 6.
10.1007/978-1-4757-3030-2 Google Scholar
- 23 E. Riedel (ed.): Moderne anorganische Chemie, Walter de Gruyter, Berlin, New York 1999, chaps. 4.3, 4.4.
- 24 M. Bochmann: Metallorganische Chemie der Übergangsmetalle, Wiley-VCH, Weinheim 1997.
- 25 F. Mathey, A. Sevin: Molecular Chemistry of the Transition Metals, Wiley, Chichester 1996.
- 26 G. Wilkinson, F.G.A. Stone, E.W. Abel (eds.): Comprehensive Organometallic Chemistry, Pergamon Press, Oxford, Part I, vols. 1–9 (1982), Part II, vols. 1–14 (1995).
- 27 L.S. Hegedus: Organische Synthese mit Übergangsmetallen, Wiley-VCH, Weinheim 1995.
- 28 P.B. Kettler: “Platinum Group Metals in Catalysis: Fabrication of Catalysts and Catalyst Precursors”, Org. Process Res. Develop. 7 (2003) 342–354.
- 29 R.M. Coates, S.E. Denmark: Handbook of Reagents for Organic Synthesis —Reagents, Auxiliaries and Catalysts for CC Bond Formation, Wiley, New York 1999.
- 30 W.A. Herrmann (ed.): “ Synthetic Methods of Organometallic and Inorganic Chemistry”, vols. 1–8, Georg Thieme Verlag, Stuttgart 1996–1997.
- 31 G. Wilkinson, F.G.A. Stone, E.W. Abel (eds.): Comprehensive Organometallic Chemistry, 2 ed., Pergamon Press, Oxford 1995.
- 32 G. Wilkinson, R.D. Gillard, J.E. McCleverty (eds.): Comprehensive Coordination Chemistry, Pergamon Press, Oxford 1987.
- 33 C.A. Tolman, J. Am. Chem. Soc. 92 (1970) 2953.
- 34 C.A. Tolman, Chem. Rev. 77 (1977) 313.
- 35 T.T. Derencsényi, Inorg. Chem. 20 (1981) 665.
- 36 T. Bartik, T. Himmler, H.-G. Schulte, K. Seevogel, J. Organomet. Chem. 272 (1984) 29.
- 37 C.A. Tolman, J. Am. Chem. Soc. 92 (1970) 2956.
- 38 C.C. Casey, G.T. Whiteker, Isr. J. Chem. 30 (1990) 299.
- 39 J. Bruckmann, C. Krüger, F. Lutz, Z. Naturforsch. B 50 (1995) 351.
- 40 E. Burello, P. Marion, J.-C. Galland, A. Chamard, G. Rothenberg, Adv. Synth. Catal. 347 (2005) 803.
- 41 P. Dierkes, P.W.N.M. van Leeuven, J. Chem. Soc. Dalton Trans. 1999, 1519.
- 42 Z. Freixa, P.W.N.M. van Leeuven, Dalton Trans. 2003, 1890.
- 43 F. Ungváry: “Application of transition metals in hydroformylation: annual survey covering the year 2004”, Coord. Chem. Rev. 249 (2005) 2946.
- 44 M. Beller, K. Kumar: Hydroformylation: Applications in the Synthesis of Pharmaceuticals and Fine Chemicals in M. Beller, C. Bolm (eds.): Transition Metals for Organic Synthesis, 2nd ed., Wiley-VCH, Weinheim 2004, chap. 2.1, p. 29.
- 45 F. Ungváry: “Application of transition metals in hydroformylation: annual survey covering the year 2003”, Coord. Chem. Rev. 248 (2004) 867.
- 46
P.W.N.M. van Leeuwen:
Homogeneous Catalysis — Understanding the Art,
Kluwer Academic Publishers,
Dordrecht
2004, chaps. 7 and 8.
10.1007/1-4020-2000-7 Google Scholar
- 47 F. Ungváry: “Application of transition metals in hydroformylation: annual survey covering the year 2002”, Coord. Chem. Rev. 241 (2003) 295.
- 48 G. Protzmann, K.-D. Wiese: “Status and Future Aspects of Industrial Hydroformylation, Erdöl Erdgas Kohle 117 (2001) 235.
- 49 P.W.N.M. Leeuwen, C. Claver (eds.): Rhodium Catalyzed Hydroformylation, Kluwer Academic Publishers, Dordrecht 2000.
- 50 C. Botteghi, M. Marchetti, S. Paganelli: New Opportunities in Hydroformylation in M. Beller, C. Bolm (eds.): Transition Metals for Organic Synthesis, vol. 1, Wiley-VCH, Weinheim 1998, chap. 2.1, p. 25.
- 51 C.D. Frohning, C.W. Kohlpaintner: Hydroformylation in B. Cornils, W.A. Herrmann (eds.): Applied Homogeneous Catalysis with Organometallic Compounds, vol. 1, VCH-Verlag, Weinheim 1996, chap. 2.1, p. 29.
- 52
M. Beller,
J. Seayad,
A. Tillack,
H. Jiao:
“Katalytische Markownikow- und Anti-Markownikow-Funktionalisierung von Alkenen und Alkinen”,
Angew. Chem.
116
(2004)
3448.
10.1002/ange.200300616 Google Scholar
- 53
N. Chatani:
Selective Carbonylations with Ruthenium Catalysts in
C. Bruneau,
P.H. Dixneuf (eds.):
Ruthenium Catalysts and Fine Chemistry,
Springer-Verlag,
Berlin
2004,
p. 173.
10.1007/b94644 Google Scholar
- 54
B. El Ali,
H. Alper:
Hydrocarboxylation and Hydroesterification Reactions by Transition Metal Complexes in
M. Beller,
C. Bolm (eds.):
Transition Metals for Organic Synthesis,
Wiley-VCH,
Weinheim
1998, chap. 2.2,
p. 49.
10.1002/9783527619399.ch2b Google Scholar
- 55
J. Tsuji,
J. Kiji:
Palladium-catalyzed Carbonylation of Allylic and Propargylic Compounds in
M. Beller,
C. Bolm (eds.):
Transition Metals for Organic Synthesis,
Wiley-VCH,
Weinheim
1998, chap. 2.3,
p. 68.
10.1002/9783527619399.ch2c Google Scholar
- 56
G. Braca (ed.):
Oxygenates by Homologation or CO Hydrogenation with Metal Complexes,
Springer-Verlag,
Berlin
1994.
10.1007/978-94-011-0874-4 Google Scholar
- 57 H. Olivier-Bourbigou: Oligomerization in B. Cornils et al. (eds.): Multiphase Homogeneous Catalysis, vol. 2, Wiley-VCH, Weinheim 2005, chap. 5.2.2.1, p. 468.
- 58
Y. Tamaru (ed.):
Modern Organonickel Chemistry,
Wiley-VCH,
Weinheim
2005.
10.1002/3527604847 Google Scholar
- 59 P.W.N.M. van Leeuwen: Alkene Oligomerization in Homogeneous Catalysis, — Understanding the Art, Kluwer Academic Publishers, Dordrecht 2004, chap. 9, p. 175.
- 60 G.W. Parshall, S.D. Ittel: Oligomerization of Olefins in Homogeneous Catalysis, 2nd ed., Wiley-Interscience, New York 1992, chap. 4.3, p. 68.
- 61 J. Skupinska: “Oligomerization of α-Olefins to Higher Oligomers”, Chem. Rev. 91 (1991) 613.
- 62
W. Keim,
A. Behr,
M. Röper:
Alkene and Alkyne Oligomerization, Cooligomerization and Telomerization Reactions in
G. Wilkinson (ed.):
Comprehensive Organometallic Chemistry,
vol. 8,
Pergamon Press,
Oxford
1982, chap. 52,
p. 371.
10.1016/B978-008046518-0.00111-2 Google Scholar
- 63 D. Vogt: Economical Applications (SHOP Process) in B. Cornils et al. (eds.): Multiphase Homogeneous Catalysis, vol. 1, Wiley-VCH, Weinheim 2005, chap. 3.3, p. 330.
- 64 S. Kuhlmann, J.T. Dixon, M. Haumann, D.H. Morgan, J. Ofili, O. Spuhl, N. Taccardi, P. Wasserscheid: “Influence of elevated temperature and pressure on the chromium-catalyzed tetramerisation of ethylene”, Adv. Synth. Catal. 348 (2006) 1200.
- 65 A. Behr, Q. Miao: “Selective rhodium catalyzed synthesis of trans-1,4-hexadiene”, Green Chem. 7 (2005) 617.
- 66 A. Behr, C. Fängewisch: “Rhodium-catalyzed synthesis of branched fatty compounds in temperature-dependent solvent systems”, J. Mol. Catal. A 197 (2003) 115.
- 67 A. Behr: “Von der Petrochemie zur Feinchemikalie: Die Oligomerisierung von Acrylverbindungen”, Erdöl Erdgas Kohle 102 (1986) 193.
- 68 W. Keim, A. Behr, B. Gruber, B. Hoffmann, F.H. Kowaldt, U. Kürschner, B. Limbäcker, F.P. Sistig: “Reactions of Chelate Ylides with Nickel(0) Complexes”, Organometallics 5 (1986) 2356.
- 69 A. Behr, W. Keim: “The Nickel-Complex Catalyzed Synthesis of α-Olefins”, Arab. J. Sci. Eng. 10 (1985) 377.
- 70 W. Keim: “Vor- und Nachteile der homogenen Übergangsmetallkatalyse, dargestellt am SHOP-Prozeß”, Chem. Ing. Tech. 56 (1984) 850.
- 71 A. Behr, M. Becker, T. Beckmann, L. Johnen, J. Leschinski, S. Reyer: “Telomerization: Advances and Applications of a Versatile Reaction”, Angew. Chem. Int. Ed. 48 (2009) 3598.
- 72 A. Behr, T. Beckmann, H. Nachtrodt: “Multiphase telomerisation of butadiene with phenol: optimisation and scale-up in different reactor types”, Dalton Trans. 2009, 6214.
- 73 A. Behr, J. Leschinski, C. Awungacha, S. Simic, T. Knoth: “Telomerization of Butadiene with Glycerol: Reaction Control through Process Engineering, Solvents and Additives”, ChemSusChem 2 (2009) 71.
- 74 A. Behr, J. Leschinski, A. Prinz, M. Stoffers: “Continuous reactive extraction for selective telomerisation of butadiene with glycerol in a miniplant”, Chem. Eng. Proc. 48 (2009) 1140.
- 75 A. Behr, M. Urschey, V.A. Brehme: “Aqueous biphasic catalysis as a powerful tool for catalyst recycling in telomerization and hydrogenation chemistry”, Green Chem. 5 (2003) 198.
- 76 A. Behr, M. Urschey: “Highly Selective Biphasic Telomerization of Butadiene with Glycols: Scope and Limitations”, Adv. Synth. Catal. 345 (2003) 1242.
- 77 A. Behr, M. Urschey: ”Palladium-catalyzed telomerization of butadiene with ethylene glycol”, J. Mol. Catal. A 197 (2003) 101.
- 78
R. Jackstell et al.:
“Ein hocheffizienter Katalysator für die Telomerisation von 1,3-Dienen mit Alkoholen”,
Angew. Chem.
114
(2002)
1028.
10.1002/1521-3757(20020315)114:6<1028::AID-ANGE1028>3.0.CO;2-# Google Scholar
- 79 A. Behr, T. Fischer, M. Grote, D. Schnitzmeier: “Verfahrenskonzepte zur übergangsmetall-katalysierten Telomerisation von Isopren mit Methanol”, Chem. Ing. Tech. 74 (2002) 1586.
- 80 F. Vollmüller, W. Mägerlein, S. Klein, J. Krause, M. Beller: “Highly Efficient Palladium-Catalyzed Telomerization of Butadiene with Methanol”, Adv. Synth. Catal. 143 (2001) 29.
- 81
T. Prinz,
W. Keim,
B. Drießen-Hölscher:
“Zweiphasenkatalyse: eine Strategie zur Vermeidung von Konsekutivreaktionen am Beispiel der Telomerisation von Butadien und Ammoniak”,
Angew. Chem.
108
(1996)
1835.
10.1002/ange.19961081533 Google Scholar
- 82
A. Behr:
Application of Telomerization and Dimerization to the Synthesis of Fine Chemicals in
A. Mortreux,
F. Petit (eds.):
Industrial Application of Homogeneous Catalysis,
Reidel Publ.,
Dordrecht
1988,
141–175.
10.1007/978-94-009-3897-7_5 Google Scholar
- 83
A. Behr:
Telomerization of Dienes by Homogeneous Transition Metal Catalysts in
R. Ugo (ed.):
Aspects of Homogeneous Catalysis,
vol. 5,
Reidel Publ.,
Dordrecht
1984,
pp. 3–73.
10.1007/978-94-009-6363-4_1 Google Scholar
- 84 T. Meyer, J. Keurentjes: Handbook of Polymer Reaction Engineering, Wiley-VCH, Weinheim 2005, chap. 8, p. 365.
- 85 M. Brahm: Polymerchemie kompakt, Hirzel-Verlag, Stuttgart 2005, chap. 1.4.
- 86 K. Albrecht et al.: Kunststoffe in Winnacker-Küchler, Chemische Technik: Prozesse und Produkte, 5th ed., vol. 5, Wiley-VCH, Weinheim 2005, p. 465.
- 87 M. Arndt-Rosenau: Elastomere in Winnacker-Küchler, Chemische Technik: Prozesse und Produkte, 5th ed., vol. 5, Wiley-VCH, Weinheim 2005, p. 821.
- 88 S. Mecking: Catalytic Polymerization in B. Cornils, W. A. Herrmann (eds.): Aqueous-Phase Organometallic Catalysis, 2nd ed., Wiley-VCH, Weinheim 2004, p. 576.
- 89 H.F. Mark: Encyclopedia of Polymer Science and Technology, 3rd ed., Wiley-VCH, Weinheim 2004.
- 90
B. Rieger,
L. Saunders Baugh,
S. Kacker,
S. Striegler:
Late Transition Metal Polymerization Catalysts,
Wiley-VCH,
Weinheim
2003.
10.1002/3527601805 Google Scholar
- 91 H.-G. Elias: An Introduction to Plastics, Wiley-VCH, Weinheim 2003, chap. 3.2.5.
- 92 J. Brandrup, E.H. Immergut, F.A. Grulke (eds.): Polymer Handbook, 4th ed., Wiley-VCH, Weinheim 2003.
- 93
M.D. Lechner,
K. Gehrke,
E.H. Nordmeier:
Makromolekulare Chemie,
3rd ed.,
Springer-Verlag,
Heidelberg
2003.
10.1007/978-3-0348-5094-0 Google Scholar
- 94
G. Wilke:
“50 Jahre Ziegler-Katalysatoren: Werdegang und Folgen einer Erfindung”,
Angew. Chem.
115
(2003)
5150.
10.1002/ange.200330056 Google Scholar
- 95
L.L. Böhm:
“Die Ethylenpolymerization mit Ziegler-Katalysatoren 50 Jahre nach der Entdeckung”,
Angew. Chem.
115
(2003)
5162.
10.1002/ange.200300580 Google Scholar
- 96 H.G. Alt (ed.): “Metallocene complexes as catalysts for olefin polymerization”, Coord. Chem. Rev. 250 (2006) 1.
- 97 H.G. Alt et al.: “Metallacyclic metallocene complexes as catalysts for olefin polymerization”, Coord. Chem. Rev. 250 (2006) 2.
- 98 P.C. Möhring, N.J. Coville: “Group 4 metallocene polymerization catalysts”, Coord. Chem. Rev. 250 (2006) 18.
- 99 A. Bastero, G. Francio, W. Leitner, S. Mecking: “Catalytic Ethylene Polymerization in Carbon Dioxide as a Reaction Medium with Soluble Nickel Catalysts”, Chem. Eur. J. 12 (2006) 6110.
- 100
S. Mecking:
“Olefin-Polymerisation durch Komplexe später Übergangsmetalle”,
Angew. Chem.
113
(2001)
550.
10.1002/1521-3757(20010202)113:3<550::AID-ANGE550>3.0.CO;2-Z Google Scholar
- 101 S.D. Ittel, L.K. Johnson, M. Brookhart: “Late-Metal Catalysts for Ethylene Homo- and Copolymerization”, Chem. Rev. 100 (2000) 1169.
- 102 S. Mecking: “Cationic nickel and palladium complexes with bidentate ligands for the C-C linkage of olefins”, Coord. Chem. Rev. 203 (2000) 325.
- 103
M. Beller,
J. Seayad,
A. Tillack,
H. Jiao:
“Katalytische Markownikow- und Anti-Markownikow-Funktionalisierung von Alkenen und Alkinen”,
Angew. Chem.
116
(2004)
3448.
10.1002/ange.200300616 Google Scholar
- 104 J. Podlech: “Introduction of the cyano group by addition to alkynes”, Sci. Synth. 19 (2004) 325.
- 105
P.W.N.M. van Leeuwen:
Hydrocyanation of Alkenes in
Homogeneous Catalysis,
Kluwer Academic Publishers,
Dordrecht
2004, chap. 11,
p. 229.
10.1007/1-4020-2000-7_11 Google Scholar
- 106 S. Bhaduri, D. Mukesh: Homogeneous Catalysis, Wiley-Interscience, New York 2000, chap. 7.7, p. 151; chap. 9.5.3, p. 223.
- 107 T.V. RajanBabu, A.L. Casalnuovo: Hydrocyanation of Carbon-Carbon Bonds in E.N. Jacobson et al. (eds.): Comprehensive Asymmetric Catalysis I–III, Springer, Berlin 1999, chap. 10, p. 367.
- 108
A.L. Casalnuovo,
T.V. RajanBabu:
Transition-metal-catalyzed alkene and alkyne hydrocyanations in
M. Beller,
C. Bolm (eds.):
Transition Metals for Organic Synthesis,
Wiley-VCH,
Weinheim
1998,
vol. 1, chap. 2.5,
p. 91;
10.1002/9783527619399.ch2e Google Scholar2nd ed., 2004, p. 149.
- 109 A.L. Casalnuovo, T.V. RajanBabu: The Asymmetric Hydrocyanation of Vinylarenes in A.N. Collins et al. (eds.): Chirality in Industry, John Wiley & Sons, Chichester 1997, chap. 15, p. 309.
- 110
K. Huthmacher,
S. Krill:
Reactions with Hydrogen Cyanide (Hydrocyanation) in
B. Cornils,
W.A. Herrmann (eds.):
Applied Homogeneous Catalysis with Organometallic Compounds,
vol. 1,
VCH-Verlag,
Weinheim
1996, chap. 2.5,
p. 465;
10.1002/9783527619351.ch2e Google Scholar2nd ed., 2004, p. 468.
- 111
W. Goertz,
P.C.J. Kamer,
P.W.N.M. van Leeuwen,
D. Vogt:
“Asymmetric Nickel-Catalyzed Hydrocyanation of Vinylarenes by Applying Homochiral Xantphos Ligands”,
Chem. Eur. J.
7
(2001)
1614.
10.1002/1521-3765(20010417)7:8<1614::AID-CHEM16140>3.0.CO;2-E CAS PubMed Web of Science® Google Scholar
- 112 M. Yan, Q.-Y. Xu, A.S.C. Chan: “Asymmetric hydrocyanation of olefins catalyzed by chiral diphosphite-nickel complexes”, Tetrahedron: Asymmetry 11 (2000) 845.
- 113 J.-P. Corbet, G. Mignani: “Selected Patented Cross-Coupling Reaction Technologies”, Chem. Rev. 106 (2006) 2651.
- 114 K.H. Shaughnessy: “Beyond TPPTS: new approaches to the development of efficient palladium-catalyzed aqueous-phase cross-coupling reactions”, Eur. J. Org. Chem. 2006, 1827.
- 115 N.T.S. Phan, M. van der Sluys, C.W. Jones: “On the nature of the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings — Homogeneous or Heterogeneous Catalysis, a Critical Review”, Adv. Synth. Catal. 348 (2006) 609.
- 116 E.N. Jacobson, A. Pfaltz, M. Shibasaki: “Catalytic C-C Bond Formation”, Special Issue, Adv. Synth. Catal. 347 (2005) 1471ff.
- 117
K.C. Nicolaou,
P.G. Bulger,
D. Sarlah:
“Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese”,
Angew. Chem.
117
(2005)
4516.
10.1002/ange.200500368 Google Scholar
- 118
U. Christmann,
R. Vilar:
“Einfach koordinierte Palladiumspezies als Katalysatoren in Kreuzkupplungen”,
Angew. Chem.
117
(2005)
370.
10.1002/ange.200461189 Google Scholar
- 119
A.C. Frisch,
M. Beller:
“Katalysatoren machen's möglich: Selektive C-C-Kupplungen mit nichtaktivierten Alkylhologeniden”,
Angew. Chem.
117
(2005)
680.
10.1002/ange.200461432 Google Scholar
- 120 W.A. Herrmann, C.-P. Reisinger, P. Härter: Heck and other C-C-Coupling Reactions in B. Cornils et al. (eds.): Multiphase Homogeneous Catalysis, vol. 1, Wiley-VCH, Weinheim 2005, chap. 2.4.4.4, p. 230.
- 121 F. Diederich, A. de Meijere: Metal Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim 2004.
- 122
J. Tsuji:
Palladium Reagents and Catalysts,
Wiley,
Chichester
2004.
10.1002/0470021209 Google Scholar
- 123 A.O. King, N. Yasuda: “Palladium-catalyzed cross-coupling reactions in the synthesis of pharmaceuticals”, Top. Organomet. Chem. 6 (2004) 205.
- 124 V. Farina: “High-turnover palladium catalysts in cross-coupling and Heck chemistry: A critical overview”, Adv. Synth. Catal. 346 (2004) 1553.
- 125 A.C. Frisch, A. Zapf, O. Briel, B. Kayser, N. Shaikh, M. Beller: “Comparison of palladium carbene and palladium phosphine catalysts for catalytic coupling reactions of aryl halides”, J. Mol. Catal. A 214 (2004) 231.
- 126
P.W.N.M. van Leeuwen:
Homogeneous Catalysis,
Kluwer Academic Publishers,
Dordrecht
2004, chap. 13,
p. 271.
10.1007/1-4020-2000-7_13 Google Scholar
- 127 W.A. Herrmann, K. Öfele, D. v. Preysing, S.K. Schneider: “Phospha-palladacycles and N-heterocyclic carbene palladium complexes: efficient catalysts for CC-coupling reactions”, J. Organomet. Chem. 687 (2003) 229.
- 128
A. Zapf:
“Neue Substrate für Palladium-katalysierte Kupplungsreaktionen von Aromaten”,
Angew. Chem.
115
(2003)
5552.
10.1002/ange.200301681 Google Scholar
- 129 A. C. Hillier, S.P. Nolan: “Palladium/nucleophilic carbene catalysts for cross-coupling reactions”, Platinum Met. Rev. 46 (2002) 50.
- 130
A.F. Littke,
G.C. Fu:
“Palladiumkatalysierte Kupplungen von Arylchloriden”,
Angew. Chem.
114
(2002)
4350.
10.1002/1521-3757(20021115)114:22<4350::AID-ANGE4350>3.0.CO;2-0 Google Scholar
- 131 E. Negishi (ed.): Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley-Interscience, New York 2002.
- 132 B. Marciniec (ed.), J. Mol. Catal. A 254 (2006) 1–208, Special issue, Contributions on the 16th International Symposium on Olefin Metathesis and Related Chemistry in Poznan/PL.
- 133
Y. Chauvin:
“Olefinmetathese: die frühen Tage” (Nobel lecture),
Angew. Chem.
118
(2006)
3825.
10.1002/ange.200601234 Google Scholar
- 134
R.R. Schrock:
“Metall-Kohlenstoff-Mehrfachbindungen in katalytischen Metathesereaktionen” (Nobel lecture),
Angew. Chem.
118
(2006)
3832.
10.1002/ange.200600085 Google Scholar
- 135
R.H. Grubbs:
“Olefinmetathesekatalysatoren zur Synthese von Molekülen und Materialien” (Nobel lecture),
Angew. Chem.
118
(2006)
3845.
10.1002/ange.200600680 Google Scholar
- 136 T.W. Funk, J.M. Berlin, R.H. Grubbs: “Highly active chiral ruthenium catalysts for asymmetric ring-closing olefin metathesis”, J. Am Chem. Soc. 128 (2006) 1840.
- 137
T.J. Donohoe,
A.J. Orr,
M. Bingham:
“Ringschlussmetathese: ein Schlüssel zur Arensynthese”,
Angew. Chem.
118
(2006)
2730.
10.1002/ange.200503512 Google Scholar
- 138 A. Mortreux, O. Coutelier: “Alkyne metathesis catalysts: Scope and future”, J. Mol. Catal. A 254 (2006) 96.
- 139
C. Bruneau,
P.H. Dixneuf:
“Metallvinylidene und -allenylidene in der Katalyse”,
Angew. Chem.
118
(2006)
2232.
10.1002/ange.200501391 Google Scholar
- 140
T.J. Katz:
“Metallcarbene mit niedriger Oxidationsstufe als Initiatoren für Olefinmetathesen”,
Angew. Chem.
117
(2005)
3070.
10.1002/ange.200462442 Google Scholar
- 141 D. Astruc: “The metathesis reactions: from a historical perspective to recent developments”, New. J. Chem. 29 (2005) 42.
- 142 R. Drozdzak et al.: “Synthesis of Schiff Base-Ruthenium Complexes”, Adv. Synth. Catal. 347 (2005) 1721.
- 143 S.J. Connon, S. Blechert: Recent Advances in Alkene Metathesis in C. Bruneau, P.H. Dixneuf (eds.): Top. Organomet. Chem., vol. 11, Springer, Berlin 2004, p. 93.
- 144 R.R. Schrock: “Recent advances in olefin metathesis”, J. Mol. Catal. A 213 (2004) 21.
- 145 R. Castarlenas, C. Fischmeister, C. Bruneau, P.H. Dixneuf: “Allenylidene-ruthenium complexes as versatile precatalysts for alkene metathesis reactions”, J. Mol. Catal. A 213 (2004) 31.
- 146 R.H. Grubbs: “Olefin metathesis”, Tetrahedron 60 (2004) 7117.
- 147
R.R. Schrock,
A.H. Hoveyda:
“Molybdän- und Wolframimidoalkylidenkomplexe als effiziente Olefinmetathesekatalysatoren”,
Angew. Chem.
115
(2003)
4740.
10.1002/ange.200300576 Google Scholar
- 148
R.H. Grubbs (ed.):
Handbook of Metathesis,
Wiley-VCH,
Weinheim
2003.
10.1002/9783527619481 Google Scholar
- 149 T. Opstal, F. Verpoort: “Easily accessible and robust olefin-metathesis catalysts”, J. Mol. Catal. A 200 (2003) 49.
- 150 B. Chen et al.: “New developments in hydrogenation catalysis”, Appl. Catal. A 2 809 (2005) 17.
- 151 P.W.N.M. van Leeuwen: Homogeneous Catalysis, Kluwer Academic Publishers, Dordrecht 1999, chap. 4, p. 75.
- 152
S. Bhaduri,
D. Mukesh:
Homogeneous Catalysis,
Wiley-Interscience,
New York
2000, chap. 7.3,
p. 135.
10.1002/0471220388 Google Scholar
- 153 A. Börner et al.: Homogeneous Hydrogenations in Transition Metals for Organic Synthesis, vol. 2, Wiley-VCH, Weinheim 1998, chap. 1.1, p. 3.
- 154 A. Börner et al.: “A new access to chiral phospholanes”, Eur. J. Org. Chem. 2006, 3412.
- 155 M. Studer, H.-U. Blaser, C. Exner: “Enantioselective hydrogenation using heterogeneous modified catalysts: An update”, Adv. Synth. Catal. 345 (2003) 45.
- 156 H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer: “Selective hydrogenation for fine chemicals: Recent trends and new developments”, Adv. Synth. Catal. 345 (2003) 103.
- 157 W.S. Knowles: “Asymmetric Hydrogenations” (Nobel lecture 2001), Adv. Synth. Catal. 345 (2003) 3.
- 158 F. Joó, A. Kathó: Hydrogenation in B. Cornils et al. (eds.): Multiphase Homogeneous Catalysis, vol. 1, Wiley-VCH, Weinheim 2005, chap. 2.4.2.1, p. 187.
- 159
F. Joó:
Aqueous Organometallic Catalysis,
Kluwer Academic Publishers,
Dordrecht
2001, chap. 3.
10.1007/0-306-47510-3 Google Scholar
- 160
R. Noyori,
T. Ohkuma:
“Asymmetrische Katalyse mit hinsichtlich Struktur und Funktion gezielt entworfenen Molekülen: die chemo- und stereoselektive Hydrierung von Ketonen”,
Angew. Chem.
113
(2001)
41.
10.1002/1521-3757(20010105)113:1<40::AID-ANGE40>3.0.CO;2-K Google Scholar
- 161
M.T. Reetz,
G. Mehler:
“Hoch enantioselektive Rh-katalysierte Hydrierungen unter Verwendung von chiralen Monophosphit-Liganden”,
Angew. Chem.
112
(2000)
4047.
10.1002/1521-3757(20001103)112:21<4047::AID-ANGE4047>3.0.CO;2-Z Google Scholar
- 162 A. Berkessel (ed.): The 9th International Symposium “Activation of dioxygen and homogeneous catalytic oxidation”, J. Mol. Catal. A 251 (2006), Special Issue.
- 163 F. Minisci, C. Punta, F. Recupero: “Mechanisms of the aerobic oxidations”, J. Mol. Catal. A 251 (2006) 129.
- 164
D. Lenoir:
“Selektive Oxidation von organischen Verbindungen”,
Angew. Chem.
118
(2006)
3280.
10.1002/ange.200502702 Google Scholar
- 165
R. B. Watson,
U. S. Ozkan:
Selective Oxidation in
V.H. Grassian (ed.):
Environmental Catalysis,
Taylor & Francis,
Boca Raton
2005,
p. 523;
10.1201/9781420027679.sec3 Google ScholarN. Jiang, C.-J. Li: Oxidation in Aqueous Media in V.H. Grassian (ed.): Environmental Catalysis, Taylor & Francis, Boca Raton 2005, p. 601.
- 166 M. Pagliaro, S. Campestrini, R. Ciriminna: “Ru-based oxidation catalysis”, Chem Soc. Rev. 34 (2005) 837.
- 167 B. Cornils et al.: Multiphase Homogeneous Catalysis, vol. 1, Wiley-VCH, Weinheim 2005, chap. 2.4.3, p. 202.
- 168 T. Punniyamurthy, S. Velusamy, J. Iqbal: “Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen”, Chem. Rev. 105 (2005) 2329.
- 169
J.-E. Bäckvall:
Modern Oxidation Methods,
Wiley-VCH,
Weinheim
2004.
10.1002/3527603689 Google Scholar
- 170 M. Beller: “The current status and future trends in oxidation chemistry”, Adv. Synth. Catal. 346 (2004) 107ff, Special Issue.
- 171
S.-I. Murahashi,
N. Komiya:
Oxidation Reactions in
S.-I. Murahashi (ed.):
Ruthenium in Organic Synthesis,
Wiley-VCH,
Weinheim
2004, chap. 3,
p. 53.
10.1002/3527603832 Google Scholar
- 172 I.W.C.E. Arends, T. Kodama, R.A. Sheldon: “Oxidation using ruthenium catalysts”, Top. Organomet. Chem. 11 (2004) 277.
- 173
P.W.N.M. van Leeuwen:
Homogeneous Catalysis,
Kluwer Academic Publishers,
Dordrecht
2004, chaps. 14, 15.
10.1007/1-4020-2000-7 Google Scholar
- 174 L.I. Simandi (ed.): Advances in Catalytic Activation of Dioxygen by Metal Complexes, Kluwer Academic Publishers, Dordrecht 2003.
- 175 S.M. Roberts, G. Poignant (eds.): Hydrolysis, Oxidation and Reduction, Wiley, Chichester 2002.
- 176
F. Joó:
Aqueous Organometallic Catalysis,
Kluwer Academic Publishers,
Dordrecht
2001, chap. 8,
p. 257.
10.1007/0-306-47510-3 Google Scholar
- 177
B.L. Feringa:
Wacker Oxidation in
M. Beller,
C. Bolm (eds.):
Transition Metals for Organic Synthesis,
vol. 2,
Wiley-VCH,
Weinheim
1998, chap. 2.8,
p. 307.
10.1002/9783527619399.ch5h Google Scholar
- 178 I.W.C.E. Arends, T. Kodama, R.A. Sheldon: “Oxidation using ruthenium catalysts”, Top. Organomet. Chem. 11 (2004) 277.
- 179 B. Drießen-Hölscher: Aminations in B. Cornils et al. (eds.): Multiphase Homogeneous Catalysis, Wiley-VCH, Weinheim 2005, vol. 1, chap. 2.4.4.5, p. 238.
- 180
J. Tsuji:
Palladium Reagents and Catalysts,
John Wiley & Sons,
Chichester
2004, chap. 8.2,
p. 605.
10.1002/0470021209 Google Scholar
- 181
M. Beller,
J. Seayad,
A. Tillack,
H. Jiao:
“Katalytische Markownikow- und Anti-Markownikow Funktionalisierung von Alkenen und Alkinen”,
Angew. Chem.
116
(2004)
3448.
10.1002/ange.200300616 Google Scholar
- 182
B.F. Straub,
R.G. Bergman:
“The Mechanism of Hydroamination of Allenes, Alkynes, and Alkenes”,
Angew. Chem.
113
(2001)
4768.
10.1002/1521-3757(20011217)113:24<4768::AID-ANGE4768>3.0.CO;2-W Google Scholar
- 183
M. Nobis,
B. Drießen-Hölscher,
“Neuere Entwicklungen bei übergangsmetall katalysierten intermolekularen Hydroaminierungen – ein Durchbruch?”,
Angew. Chem.
113
(2001)
4105.
10.1002/1521-3757(20011105)113:21<4105::AID-ANGE4105>3.0.CO;2-0 Google Scholar
- 184
M. Beller,
T.H. Riermeier:
Transition Metal-Catalyzed C-N and C-O Forming Reactions in
M. Beller,
C. Bolm (eds.):
Transition Metals for Organic Synthesis,
vol. 1,
Wiley-VCH,
Weinheim
1998, chap. 2.11,
p. 184.
10.1002/9783527619399.ch2k Google Scholar
- 185
H.C. Kolb,
K.B. Sharpless:
Asymmetric Aminohydroxylation in
M. Beller,
C. Bolm (eds.):
Transition Metals for Organic Synthesis,
vol. 2,
Wiley-VCH,
Weinheim
1998, chap. 2.6,
p. 243.
10.1002/9783527619399.ch5f Google Scholar
- 186
T.E. Müller,
M. Beller:
Hydroamination of Alkenes and Alkynes in
M. Beller,
C. Bolm (eds.):
Transition Metals for Organic Synthesis,
vol. 2,
Wiley-VCH,
Weinheim
1998, chap. 2.9,
p. 316.
10.1002/9783527619399.ch5i Google Scholar
- 187 S.L. Buchwald, C. Mauger, G. Mignani, U. Scholz: “Industrial-scale palladium-catalyzed coupling of aryl halides and amines — A personal account”, Adv. Synth. Catal. 348 (2006) 23.
- 188
S.L. Buchwald et al.:
“Monodentate Phosphines Provide Highly Active Catalysts for Pd-Catalyzed C-N Bond-Forming Reactions”,
Angew. Chem.
118
(2006)
6673.
10.1002/ange.200601612 Google Scholar
- 189 K.C. Hultzsch:, “Transition metal-catalyzed asymmetric hydroamination of alkenes”, Adv. Synth. Catal. 347 (2005) 367.
- 190 S. Blechert et al.: “Intramolekulare Hydroamination of Functionalized Alkenes and Alkynes”, Angew. Chem. 44 (2005) 7794.
- 191
P.W.N.M. van Leeuwen:
Isomerisation in
Homogeneous Catalysis,
Kluwer Academic Publishers,
Dordrecht
2004, chap. 5,
p. 101.
10.1007/1-4020-2000-7_5 Google Scholar
- 192
S. Bhaduri,
D. Mukesh:
Homogeneous Catalysis,
Wiley-Interscience,
New York
2000, chaps. 7.2, 9.3.2.
10.1002/0471220388 Google Scholar
- 193
S. Otsuka,
K. Tami:
Isomerization of Olefins and the Related Reactions in
M. Beller,
C. Bolm (eds.):
Transition Metals for Organic Synthesis,
vol. 1,
Wiley-VCH,
Weinheim
1998, chap. 2.9,
p. 147.
10.1002/9783527619399.ch2i Google Scholar
- 194 W.A. Herrmann: Double-Bond Isomerisation of Olefins in B. Cornils, W.A. Herrmann (eds.): Applied Homogeneous Catalysis with Organometallic Compounds, vol. 2, VCH, Weinheim 1996, chap. 3.2.14, p. 980.
- 195 C.J. Yue, Y. Liu, R. He: “Olefins isomerization by hydride complexes of ruthenium”, J. Mol. Catal. A 259 (2006) 17.
- 196 T.C. Morril, C.A. de Souza: “Efficient hydride-assisted isomerization of alkenes via rhodium catalysis”, Organometallics 22 (2003) 1626.
