Transition Metal Catalysis in Fluorous Media: Practical Application of a New Immobilization Principle to Rhodium-Catalyzed Hydroboration

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 15, 1997, Pages 1610-1612

  Juliette, Jerrick J J ^a   Horváth, István T ^b   Gladysz, J A ^a  

^a UNIVERSITY OF UTAH   (United States)

^b EXXONMOBIL UPSTREAM RESEARCH COMPANY   (United States)

Author keywords

Fluorocarbons; Hydroborations; Immobilization; Rhodium; Two phase catalysis

Indexed keywords

EID: 0030867666     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199716101     Document Type: Article

References (30)

1. a) B. Cornils, W. A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1996;
2. b) B. Cornils, Angew. Chem. 1995, 107, 1709; Angew. Chem. Int. Ed. Engl. 1995, 34, 1575.
3. b) B. Cornils, Angew. Chem. 1995, 107, 1709; Angew. Chem. Int. Ed. Engl. 1995, 34, 1575.
4. a) I. T. Horváth, J. Rábai, Science 1994, 266, 72;
5. b) US-A Patent 5,463,082, 1995.
6. c) The term "fluorous" was introduced as an analog to "aqueous" for highly fluorinated alkane, ether, and tertiary amine solvents.
7. J. A. Gladysz, Science 1994, 266, 55.
8. R. P. Hughes, H. A. Trujillo, Organometallics 1996, 15, 286.
9. a) D. P. Curran, S. Hadida, J. Am. Chem. Soc. 1996, 118, 2531;
10. b) S. G. DiMagno, P. H. Dussault, J. A. Schultz, ibid. 1996, 118, 5312;
11. c) D. P. Curran, M. Hoshino, J. Org. Chem. 1996, 61, 6480.
12. Rhodium catalysts: a) D. Männig, H. Nöth, Angew. Chem. 1985, 97, 854; Angew. Chem. Int. Ed. Engl. 1985, 24, 878;
13. Rhodium catalysts: a) D. Männig, H. Nöth, Angew. Chem. 1985, 97, 854; Angew. Chem. Int. Ed. Engl. 1985, 24, 878;
14. b) D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1992, 114, 6671;
15. c) D. A. Evans, G. C. Fu, B. A. Anderson, ibid. 1992, 114, 6679;
16. d) S. A. Westcott, H. P. Blom, T. B. Marder, R. T. Baker, ibid. 1992, 114, 8863;
17. e) K. Burgess, W. A. van der Donk, S. A. Westcott, T. B. Marder, R. T. Baker, J. C. Calabrese, ibid. 1992, 114, 9350;
18. f) J. M. Brown, G. C. Lloyd-Jones, ibid. 1994, 116, 866;
19. g) S. Pereira, M. Srebnik, ibid. 1996, 118, 909.
20. Nonrhodium catalysts: a) K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179;
21. b) X. He, J. F. Hartwig, J. Am. Chem. Soc. 1996, 118, 1696.
22. 3] and 2 react in the absence of alkenes to give complex mixtures of rhodium hydrides and redistribution products, many of which may independently participate in or inhibit catalysis [6e]. Catalyst leaching has not been detected to date, but further studies are in progress.
23. b) A similar five-cycle sequence with styrene (515 equiv per cycle, 8 h, room temperature) gave mixtures of branched and linear organoboranes (56:44 to 51:49) in 92, 96, 89, 58, and 77% yields (TON 471, 496, 457, 300, and 396, respectively).
24. 6) give nearly the same isomer ratios for all styrenes.
25. H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1975, 97, 5249.
26. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
27. S. D. Brown, R. W. Armstrong, J. Am. Chem. Soc. 1996, 118, 6331.
28. J. J. J. Juliette, D. Rutherford, C. Rocoboy, unpublished results.
29. M.-A. Guillevic, A. M. Arif, I. T. Horvàth, J. A. Gladysz, Angew. Chem. 1997, 109, 1685; Angew. Chem. Int. Ed. Engl. 1997, 36, 1612.
30. M.-A. Guillevic, A. M. Arif, I. T. Horvàth, J. A. Gladysz, Angew. Chem. 1997, 109, 1685; Angew. Chem. Int. Ed. Engl. 1997, 36, 1612.