Transition Metal Catalyzed Oxidations in Perfluorinated Solvents

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 13-14, 1997, Pages 1454-1456

  Klement, Ingo ^a   Lütjens, Henning ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Epxidations; Fluorine; Homogeneous catalysis; Oxidations; Ruthenium

Indexed keywords

EID: 0030864681     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199714541     Document Type: Article

References (22)

1. J. G. Riess, M. Le Blanc, Pure Appl. Chem. 1982, 54, 2383; J. G. Riess, New. J. Chem. 1995, 19, 893; V. W. Sadtler, M. P. Krafft, J. G. Riess, Angew. Chem. 1996, 108, 2106; Angew. Chem. Int. Ed. Engl. 1996, 35, 1976.
2. J. G. Riess, M. Le Blanc, Pure Appl. Chem. 1982, 54, 2383; J. G. Riess, New. J. Chem. 1995, 19, 893; V. W. Sadtler, M. P. Krafft, J. G. Riess, Angew. Chem. 1996, 108, 2106; Angew. Chem. Int. Ed. Engl. 1996, 35, 1976.
3. J. G. Riess, M. Le Blanc, Pure Appl. Chem. 1982, 54, 2383; J. G. Riess, New. J. Chem. 1995, 19, 893; V. W. Sadtler, M. P. Krafft, J. G. Riess, Angew. Chem. 1996, 108, 2106; Angew. Chem. Int. Ed. Engl. 1996, 35, 1976.
4. J. G. Riess, M. Le Blanc, Pure Appl. Chem. 1982, 54, 2383; J. G. Riess, New. J. Chem. 1995, 19, 893; V. W. Sadtler, M. P. Krafft, J. G. Riess, Angew. Chem. 1996, 108, 2106; Angew. Chem. Int. Ed. Engl. 1996, 35, 1976.
5. C. M. Sharts, H. R. Reese, J. Fluorine Chem. 1978, 11, 637 and references therein.
6. I. T. Horváth, J. Rabai, Science 1994, 260, 72; US-A 5463082, 1995; I. T. Horváth in Applied Homogeneous Catalysis with Organometallic Compounds, (Eds.: B. Cornus, W. Herrmann), VCH, 1996, 601.
7. I. T. Horváth, J. Rabai, Science 1994, 260, 72; US-A 5463082, 1995; I. T. Horváth in Applied Homogeneous Catalysis with Organometallic Compounds, (Eds.: B. Cornus, W. Herrmann), VCH, 1996, 601.
8. I. T. Horváth, J. Rabai, Science 1994, 260, 72; US-A 5463082, 1995; I. T. Horváth in Applied Homogeneous Catalysis with Organometallic Compounds, (Eds.: B. Cornus, W. Herrmann), VCH, 1996, 601.
9. For recent applications of perfluorinated solvents for the performance of organic reactions see: S. M. Pereira, G. P. Savage, G. W. Simpson, Synth. Commun. 1995, 25, 1023; R. P. Hughes, H. A. Trujillo, Organometallics 1996, 15, 286; D. P. Curran, S. Hadida, J. Am. Chem. Soc. 1996, 118, 2531 ; D. P. Curran, M. Hoshino, J. Org. Chem. 1996, 61, 6480.
10. For recent applications of perfluorinated solvents for the performance of organic reactions see: S. M. Pereira, G. P. Savage, G. W. Simpson, Synth. Commun. 1995, 25, 1023; R. P. Hughes, H. A. Trujillo, Organometallics 1996, 15, 286; D. P. Curran, S. Hadida, J. Am. Chem. Soc. 1996, 118, 2531 ; D. P. Curran, M. Hoshino, J. Org. Chem. 1996, 61, 6480.
11. For recent applications of perfluorinated solvents for the performance of organic reactions see: S. M. Pereira, G. P. Savage, G. W. Simpson, Synth. Commun. 1995, 25, 1023; R. P. Hughes, H. A. Trujillo, Organometallics 1996, 15, 286; D. P. Curran, S. Hadida, J. Am. Chem. Soc. 1996, 118, 2531 ; D. P. Curran, M. Hoshino, J. Org. Chem. 1996, 61, 6480.
12. For recent applications of perfluorinated solvents for the performance of organic reactions see: S. M. Pereira, G. P. Savage, G. W. Simpson, Synth. Commun. 1995, 25, 1023; R. P. Hughes, H. A. Trujillo, Organometallics 1996, 15, 286; D. P. Curran, S. Hadida, J. Am. Chem. Soc. 1996, 118, 2531 ; D. P. Curran, M. Hoshino, J. Org. Chem. 1996, 61, 6480.
13. I. Klement, P. Knochel, Synlett 1995, 1113.
14. I. Klement, P. Knochel, Synlett 1996, 1004.
15. C. Massyn, R. Pastor, A. Cambon, Bull. Soc. Chim. Fr. 1974, 5, 975; A. E. Pedler, R. C. Smith, J. C. Tatlow, J. Fluorine Chem. 1971, 1, 433.
16. C. Massyn, R. Pastor, A. Cambon, Bull. Soc. Chim. Fr. 1974, 5, 975; A. E. Pedler, R. C. Smith, J. C. Tatlow, J. Fluorine Chem. 1971, 1, 433.
17. Aromatic aldehydes bearing electron-withdrawing groups are not readily oxidized by oxygen in the absence of a metal catalyst (see Scheme 4).
18. T. Yamada, T. Takai, O. Rhode, T. Mukaiyama Chem. Lett. 1991, 1 ;
19. T. Ya- mada, O. Rhode, T. Takai, T. Mukaiyama ibid. 1991, 5.
20. The ruthenium catalyst could be recovered in over 95% (by weight) from the fluorous phase after several reaction cycles.
21. A slow autoxidation was found to occur within 60 h under the reaction conditions in the absence of the ruthenium catalyst.
22. For a recent Mn-catalyzed epoxidation using a perfluorinated porphyrin ligand see: G. Pozzi, S. Banfi, A. Manfredi, F. Montanari, S. Quici, Tetrahedron 1996, 52, 11879.