Low-valent ruthenium and iridium hydride complexes as alternatives to Lewis acid and base catalysts

Accounts of Chemical Research

Volumn 33, Issue 4, 2000, Pages 225-233

  Murahashi, Shun Ichi ^a   Takaya, Hikaru ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; AMMONIA; IRIDIUM; IRIDIUM COMPLEX; NITRILE; RUTHENIUM; RUTHENIUM COMPLEX;

AMIDATION; ARTICLE; CATALYSIS; CATALYST; CHEMISTRY; ESTERIFICATION; HYDRATION;

CATALYSIS; IRIDIUM; NITRILES; RUTHENIUM;

EID: 0034008092     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar980085x     Document Type: Article

References (42)

1. (a) Sheldon, R. A. Catalysis and Pollution Prevention. Chem. Ind. 1997, 12-15.
2. (b) Sheldon, R. A. Catalysis: The Key to Waste Minimization. J. Chem. Technol. Biotechnol. 1997, 68, 381-388.
3. Naota, T.; Takaya, H.; Murahashi, S.-I. Ruthenium-Catalyzed Reactions for Organic Synthesis. Chem. Rev. 1998, 98, 2599-2660.
4. Bosnich, B. Transition-Metal-Based Lewis Acid Catalysts. Aldrichimica Acta 1998, 31, 76-83.
5. (a) Odenkirk, W.; Rheingold, A. L.; Bosnich, B. Homogeneous Catalysis: A Ruthenium-Based Lewis-Acid Catalyst for the Diels-Alder Reaction J. Am. Chem. Soc. 1992, 714, 6392-6398.
6. (b) Faller, J. M.; Ma, Y. Use of Organometallic Complexes of Ruthenium in The Lewis Acid-Catalyzed Hetero Diels-Alder Reaction. Tetrahedron Lett. 1989, 30, 1189-1192.
7. (c) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. A Stable and Recoverable Chiral Ru Lewis Acids: Synthesis, Asymmetric Diels-Alder Catalysis and Structure of Lewis Acid Methacrolein Complex. Angew. Chem., Int. Ed. 1999, 38, 1220-1223.
8. Murahashi, S.-I.; Naota, T.; Saito, E. Ruthenium-Catalyzed Amidation of Nitriles with Amines. A Novel Facile Route to Amides and Polyamides. J. Am. Chem. Soc. 1986, 708, 7846-7847.
9. Murahashi, S.-I.; Sasao, S.; Saito, E.; Naota, T. Ruthenium-Catalyzed Hydration of Nitrites and Transformation of δ-Keto Nitriles to Ene-Lactams. J. Org. Chem. 1992, 57, 2521-2523.
10. Naota, T.; Sasao, S.; Tanaka, K.; Yamamoto, H.; Murahashi, S.-I. Selenium- and Palladium-Catalyzed Oxidative Cleavage of Ene-lactams with Hydrogen Peroxide. Convenient Methods for Synthesis of Macrocyclic Ketoimides and N-Fused Azabicyclic Compounds. Tetrahedron Lett. 1993, 34, 4843-4846.
11. Murahashi, S.-I.; Sasao, S.; Saito, E.; Naota, T. Ruthenium-Catalyzed Hydration of Nitriles and Transformation of δ-Ketonitriles to Ene-Lactams: Total Synthesis of (-)-Pumiliotoxin C. Tetrahedron 1993, 49, 8805-8826.
12. Betty, R. P. Improved Process for Reductive Hydrolysis of Nitriles. PCT Int. Appl. WO9623753, 1996.
13. Yamada, H.; Kobayashi, M. Nitrile Hydratase and Its Application to Industrial Production of Acrylamide. Biosci. Biotechol. Biochem. 1996, 60, 1391-1400.
14. Huang, W.; Jia, J.; Cummings, J.; Nelson, M.; Shneider, G.; Lindqvist, Y. Crystal Structure of Nitrile Hydratase Reveals a Novel Iron Center in a Novel Fold. Structure 1997, 5, 691-699.
15. (a) Murahashi, S.-I.; Ito, K.; Naota, T.; Maeda, Y. Ruthenium Catalyzed Transformation of Alcohols to Esters and Lactones. Tetrahedron Lett. 1981, 22, 5327-5330.
16. (b) Murahashi, S.-I.; Ito, K.; Naota, T.; Maeda, Y.; Taki, H. Ruthenium-Catalyzed Oxidative Transformation of Alcohols and Aldehydes to Esters and Lactones. J. Org. Chem. 1987, 52, 4319-4327.
17. Naota, T.; Shichijo, Y.; Murahashi, S.-I. Ruthenium Complex Catalyzed Condensation of Nitriles with Alcohols. J. Chem. Soc., Chem. Commun. 1994, 1359-1360.
18. Parshall, G. W.; Ittel. S. D. Homogeneous Catalysis, 2nd ed.; Wiley: New York, 1980; pp 42-46.
19. Hartmut, L. Preparation of Polyamides from Dinitriles. Eur. Patent Appl. EP684271, 1995.
20. Achhammer, G.; Basler, P.; Fischer, R.; Fuchs, E.; Luyken, H.; Schnurr, W.; Voit, G.; Hilprecht, L. Manufacture of Caprolactam and Hexamethylenediamine Simultaneously from Adiponitrile. German Patent DE19548289, 1997.
21. O'Sullivan, D. A. DSM Shifting Emphasis From Commodities to Specialties. Chem. Eng. News 1986, March 3, 21-25.
22. (a) Anderson, B. A.; Bergman, R. G.; Mobley, T.; Peterson, T. H. Selective Intermolecular Carbon-Hydrogen Bond Activation by Synthetic Metal Complexes in Homogeneous Solution. Acc. Chem. Res. 1995, 28, 154-162.
23. (b) Shilov, A. E.; Shul'pin, G. B. Activation of C-H Bonds by Metal Complexes. Chem. Rev. 1997, 97, 2879-2932.
24. (a) Murahashi, S.-I. Synthetic Aspects of Metal-Catalyzed Oxidations of Amines and Related Reactions. Angew. Chem., Int. Ed. Engl. 1995, 34, 2443-2465.
25. (b) Meunier, B. Metalloporphyrins as Versatile Catalysts for Oxidation Reactions and Oxidative DNA Cleavage. Chem. Rev. 1992, 92, 1411-1456.
26. (a) Murahashi, S.-I.; Hirano, T.; Yano, T. Palladium Catalyzed Amine Exchange Reaction of Tertiary Amines. Insertion of Palladium(0) into Carbon-Hydrogen Bonds. J. Am. Chem. Soc. 1978, 100, 348-349.
27. (b) Murahashi, S.-I.; Watanabe, T. Palladium Catalyzed Hydrolysis of Tertiary Amines with Water. J. Am. Chem. Soc. 1979, 107, 7429-7430.
28. Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. Ruthenium Catalyzed Aldol and Michael Reactions of Activated Nitriles. J. Am. Chem. Soc. 1989, 111, 5954-5955.
29. Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. Ruthenium-Catalyzed Aldol and Michael Reactions of Nitriles. Carbon-Carbon Bond Formation by α-C-H Activation of Nitriles. J. Am. Chem. Soc. 1995, 117, 12436-12451.
30. Komiya, S.; Mizuho, Y.; Kasuga, N. C-H Activation by Ruthenium-(O) Complexes. Isolation of an Active Intermediate in the Ruthenium Catalyzed Aldol and Michael Reactions. Chem. Lett. 1991, 2127-2130.
31. Lin, Y.; Zhu, X.; Xiang, M. Transition Metal Polyhydrides-Catalyzed Addition of Activated Nitriles to Aldehydes and Ketones via Knoevenagel Condensation. J. Organomet. Chem. 1993, 448, 215-218.
32. Hirano, M.; Hirai, M.; Ito, Y.; Tsurumaki, T.; Baba, A.; Fukuoka, A.; Komiya, S. N-Bonded Enolatorhenium(I) Complexes Having Dimethylphenylphosphine Ligands as Active Key Intermediates in Catalytic Knoevenagel and Michael Reactions. J. Organomet. Chem. 1998, 569, 3-14.
33. 2 to Aldehydes. J. Chem. Soc., Chem. Commun. 1994, 1665-1666.
34. (a) Murahashi, S.-I.; Naota, T.; Maezaki, M. Rhodium-Catalyzed Michael Additions of Activated Nitriles. Presented at the 61st Annual Meetings of the Chemical Society of Japan, Yokohama, March 29-April 1, 1991; Abstract 1C940.
35. (b) Paganelli, S.; Schionato, A.; Botteghi, C. Rhodium-Catalyzed Michael Additions of Activated Nitriles to α,β-Unsaturated Esters. Tetrahedron Lett. 1991, 32, 2807.
36. Sawamura, M.; Hamashima, H.; Ito, Y. Catalytic Asymmetric Synthesis with Trans-Chelating Chiral Diphosphine Ligand TRAP: Rhodium-Catalyzed Asymmetric Michael Addition of α-Cyano Carboxylates. J. Am. Chem. Soc. 1992, 114, 8295-8296.
37. Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. Transition Metal Catalyzed Addition of Certain Nucleophiles to Imines. J. Am. Chem. Soc. 1994, 116, 3161-3162.
38. Inagaki, K.; Nozaki, K.; Takaya, H. Asymmetric Michael Reaction of α-Cyano Esters Catalyzed by Chiral Rh(I) Complexes with a New Optically Active Bisphosphine Ligand. Synlett 1997, 119-120.
39. 1-O-Enolatoruthenium(II) Complexes Derived from Ru(COD)(COT), Diphosphine, and Dimethyl Malonate. Tetrahedron Lett. 1998, 39, 5290-5212.
40. 4]. J. Am. Chem. Soc. 1996, 118, 8553-8565.
41. Takaya, H.; Naota, T.; Murahashi, S.-I. Iridium Hydride Complex Catalyzed Addition of Nitriles to Carbon-Nitrogen Triple Bonds of Nitriles. J. Am. Chem. Soc. 1998, 120, 4244-4245.
42. Stack, J. G.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. Rhenium 2-Oxoalkyl (Enolate) Complexes: Synthesis and Carbon-Carbon Bond-Forming Reactions with Nitriles. Organometallics 1990, 9, 453-466.