Phosphiranes as ligands for platinum catalysed hydrosilylations

Tetrahedron

Volumn 56, Issue 1, 2000, Pages 143-156

  Liedtke, Jürgen ^a   Loss, Sandra ^a   Widauer, Christoph ^a   Grützmacher, Hansjörg ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Catalysis; Hydrosilylation; Phosphiranes; Phosphorus; Platinum

Indexed keywords

LIGAND; PHOSPHINE DERIVATIVE; PHOSPHORUS; PLATINUM; PLATINUM COMPLEX;

CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CONFERENCE PAPER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033982263     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00783-8     Document Type: Conference Paper

References (59)

1. For recent calculations see: (a) Bode, B. M.; Day, P. N.; Gordon, M. S. J. Am. Chem. Soc. 1998, 120, 1552 and references therein,
2. (b) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J. Am. Chem. Soc. 1994, 116, 7258.
3. (c) Sakaki, S.; Ikeki, M. J. Am. Chem. Soc. 1993, 115, 2373.
4. An overview about some experimental aspects is given by: Lewis, L. N.; Sy, K. G.; Bryant, Jr., G. L.; Donahue, P. E. Organometallics 1991, 10, 3750 and references therein.
5. (a) Albright, T. A.; Burdett, J. K.; Whangbo, M.-H. Orbital Interactions in Chemistry; Wiley: New York, 1985; p 140.
6. (b) Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653 and references therein.
7. Recent reviews: (a) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: New York, 1998; p 182.
8. (b) Mathey, F.; Regitz, M. Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier: Amsterdam, 1996; p 277.
9. (c) Mathey, F. Chem. Rev. 1990, 90, 997.
10. Only selected recent publications are given here which point out the names of research groups involved the synthesis and chemistry of phosphiranes: (a) Mézailles, N.; Fanwick, P. E.; Kubiak, C. P. Organometallics 1997, 16, 1526.
11. (b) Li, X.; Robinson, K. D.; Gaspar, P. P. J. Org. Chem. 1996, 61, 7702.
12. (c) Hockless, D. R.; Kang, Y.; McDonald, M. A.; Pabel, M.; Willis, A. C.; Wild, S. B. Organometallics 1996, 15, 1301.
13. (d) Marinetti, A.; Ricard, L.; Mathey, F. Synthesis 1992, 157.
14. (e) Marinetti, A.; Mathey, F. Tetrahedron Lett. 1987, 28, 5021.
15. (f) Tsuji, K.; Sasaki, S.; Yoshifuji, M. Heteroat. Chem. 1998, 7, 607.
16. (g) Review: Mathey, F. Angew. Chem. 1987, 99, 285; Angew. Chem., Int. Ed. Engl. 1987, 26, 275.
17. (g) Review: Mathey, F. Angew. Chem. 1987, 99, 285; Angew. Chem., Int. Ed. Engl. 1987, 26, 275.
18. (h) Krill, S.; Wang, B.; Hung, J.-T.; Horan, C. J.; Gray, G. M.; Lammertsma, K. J. Am. Chem. Soc. 1997, 119, 8432.
19. (i) Becker, P.; Brombach, H.; David, O.; Leuer, M.; Metternich, H.-J.; Niecke, E. Chem. Ber. 1992, 125, 111.
20. (j) Kolodiazhnyi, O. I.; Gishkun, V. E. Heteroat. Chem. 1998, 9, 659.
21. (k) Yoshifuji, M.; Toyota, K.; Yoshimura, H.; Hirotsu, K.; Okamoto, A. J. Chem. Soc., Chem. Commun. 1991, 124.
22. Manz, B.; Maas, G. J. Chem. Soc., Chem. Commun. 1995, 25.
23. (m) Lentz, D.; Marschall, R. Z. Anorg. Allg. Chem. 1992, 617, 53.
24. (n) Yoshifuji, M.; Yoshimura, H.; Toyota, K. Chem. Lett. 1990, 827.
25. (o) Schnurr, W.; Regitz, M. Tetrahedron Lett. 1989, 30, 3951.
26. (p) Märkl, G.; Hohenweider, K.; Ziegler, M. L.; Nuber, B. Tetrahedron Lett. 1990, 31, 4849.
27. (q) Märkl, G.; Hölzl, W. Tetrahedron Lett. 1989, 30, 4501.
28. (r) Zablocka, M.; Miquel, Y.; Igau, A.; Majoral, J. P.; Skowronska, A. J. Chem. Soc., Chem. Commun. 1998, 1177.
29. [2+1] cycloreversions: (a) Gaspar, P. P.; Li, X.; Silverman, J.; Haile, T.; Pae, D. H.; Xiao, M. Prog. Organosilicon Chem. (Jubilee Int. Symp. Organosilicon Chem.), 10th ed.; Mariniec, B., Chojnowski, J., Eds.; 1995; p 247.
30. (b) Li, X.; Weissman, S. I.; Lin, T.-S.; Gaspar, P. P. J. Am. Chem. Soc. 1994, 116, 7899 and references therein.
31. Retro-electrocyclisation: Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723.
32. Ring-chain rearrangements: Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771.
33. (e) Recent reports on thermal rearrangements of phosphirane complexes: Wang, B.; Lake, C. H.; Lammertsma, K. J. Am. Chem. Soc. 1996, 118, 1690.
34. (f) Huy, N. H. T.; Mathey, F. Synlett. 1995, 353.
35. (g) Flash pyrolysis of phosphiranes: Haber, LeFloch, P.; Mathey, F. Phosphorus, Sulfur and Silicon 1993, 75, 225.
36. (h) Kobayashi, S.; Kadokawa, J.-I. Marcomol. Rapid Commun. 1994, 15, 567; Surface phosphinidenes [RP(Mg] have been proposed: Bock, H.; Bankmann, M. J. Chem. Soc., Chem. Commun. 1989, 1130.
37. (h) Kobayashi, S.; Kadokawa, J.-I. Marcomol. Rapid Commun. 1994, 15, 567; Surface phosphinidenes [RP(Mg] have been proposed: Bock, H.; Bankmann, M. J. Chem. Soc., Chem. Commun. 1989, 1130.
38. Marinetti, A.; Mathey, F.; Ricard, L. Organometallics 1993, 12, 1207.
39. (a) C: Binger, P.; Leisinger, S.; Regitz, M.; Bergsträsser, U.; Bruckmann, J.; Krüger, C. J. Organomet. Chem. 1997, 529, 215 and references therein,
40. (b) D: Hu, D.; Schäufele, H.; Pritzkow, H.; Zenneck, U. Angew. Chem. 1989, 101, 929; Angew. Chem., Int. Ed. Engl. 1989, 28, 900.
41. (b) D: Hu, D.; Schäufele, H.; Pritzkow, H.; Zenneck, U. Angew. Chem. 1989, 101, 929; Angew. Chem., Int. Ed. Engl. 1989, 28, 900.
42. (c) E: Avarvari, N.; Ricard, L.; Mathey, F.; Le Floch, P.; Löber, O.; Regitz, M. Eur. J. Org. Chem. 1998, 2039.
43. (d) F: Heydt, H.; Bergsträsser, U.; Fässler, R.; Fuchs, E.; Kamel, N.; Mackewitz, T.; Michels, G.; Rösch, W.; Regitz, M.; Mazerolles, P.; Laurent, C.; Faucher, A. Bull. Soc. Chim. Fr. 1995, 132, 652.
44. (e) Also, P4 (G) is a quite stable molecule.
45. Liedtke, J.; Loss, S.; Alcaraz, G.; Gramlich, V.; Grützmacher, H. Angew. Chem. 1999, 111, 1724; Angew. Chem. Int. Ed. Engl. 1999, 38, 1623.
46. Liedtke, J.; Loss, S.; Alcaraz, G.; Gramlich, V.; Grützmacher, H. Angew. Chem. 1999, 111, 1724; Angew. Chem. Int. Ed. Engl. 1999, 38, 1623.
47. (a) Hockless, D. C. R.; McDonald, M. A.; Pabel, M.; Wild, S. B. J. Organomet. Chem. 1997, 529, 189.
48. (b) For π-exchange reactions of phosphiranium salts see: Sølling, T. I.; McDonald, M. A.; Wild, S. B.; Radom, L. J. Am. Chem. Soc. 1998, 120, 7063.
49. Nguyen, M. T.; Van Praet, E.; Vanquickenborne, L. G. Inorg. Chem. 1994, 33, 1153.
50. Pregosin, P. S. Annual Reports on NMR Spectroscopy 1986, 17, 285.
51. Al Juaid, S. S.; Carmichael, D.; Hitchcock, P. B.; Marinetti, A.; Mathey, F.; Nixon, J. A. J. Chem. Soc., Dalton Trans. 1991, 905.
52. (a) Carmichael, D.; Hitchcock, P. B.; Nixon, J. F.; Mathey, F.; Ricard, L. J. Chem. Soc., Dalton Trans. 1993, 1811 and references therein.
53. (b) Ajulu, F. A.; Hitchcock, P. B.; Mathey, F.; Michelin, R. A.; Nixon, J. A.; Pombeiro, A. J. L. J. Chem. Soc., Chem. Commun. 1993, 142.
54. 3-group in 11b and 21 were disordered over 2 or 3 positions, respectively. In structure 21 five partially occupied atoms equivalent to carbon were refined to describe one disordered THF molecule. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Data Centre as supplementary publication nos. CCDC-119359 (4a); 106558 (8); 119356 (11b); 119357 (13); 119358 (21). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB21EZ, UK (fax: +44-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
55. (a) Chandra, G.; Lo, P. Y.; Hitchcock, P. B.; Lappert, M. F. Organometallics 1987, 6, 191.
56. (b) Hitchcock, P. B.; Lappert, M. F.; Warhurst, N. J. W. Angew. Chem. 1991, 103, 439; Angew. Chem., Int. Ed. Engl. 1991, 30, 438.
57. (b) Hitchcock, P. B.; Lappert, M. F.; Warhurst, N. J. W. Angew. Chem. 1991, 103, 439; Angew. Chem., Int. Ed. Engl. 1991, 30, 438.
58. A reaction catalysed by such a catalyst may be called Park&Ride catalysis and finds prominent precedence in biological systems.
59. Kessler, H. In Methoden der Organischen Chemie, (Houben-Weyl); Müller, E., Ed.; Thieme: Stuttgart, 1972; Vol. 5/1d, p 301.