A new rhodium catalyst: Formation of [Rh(CO)4]+ in concentrated sulfuric acid and its application to carbonylation of olefins

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1540-1543

  Xu, Qiang ^a   Nakatani, Hisako ^a   Souma, Yoshie ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBONYL DERIVATIVE; RHODIUM COMPLEX; SULFURIC ACID;

ARTICLE; CATALYST; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS;

EID: 0034629359     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991659u     Document Type: Article

References (52)

1. For leading references, see: (a) Falbe, J. , Ed. New Syntheses with Carbon Monoxide; Springer-Verlag: Berlin, 1980.
2. (b) Colquhoun, H. M. ; Thompson, D. J. ; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds', Plenum Press: New York, 1991.
3. (a) Barnes, L. A. ; Rosi, M. ; Bauschlicher, C. W. , Jr. J. Chem. Phys. 1991, 94, 2031.
4. (b) Pierloot, K; Verhulst, J. ; Verbeke, P. ; Vanquickenborne, L. G. Inorg. Chem. 1989, 28, 3059.
5. Sherwood, D. E. , Jr. ; Hall, M. B. Inorg. Chem. 1980, 19, 1805.
6. Hall, M. B. ; Fenske, R. F. Inorg. Chem. 1972, 11, 1619.
7. (a) Bernhardt, E. ; Bley, B. ; Wartchow, R. ; Willner, H. ; Bill, E. ; Kühn, P. ; Sham, I. H. T. ; Bodenbinder, M. ; Bröchler, R. ; Aubke, F. J. Am. Chem. Soc. 1999, 121, 7188.
8. (b) Bröchler, R. ; Freidank, D. ; Bodenbinder, M. ; Sham, I. H. T. ; Willner, H. ; Rettig, S. J. ; Trotter, J. ; Aubke, F. Inorg. Chem. 1999, 38, 3684.
9. Willner, H. ; Aubke, F. Angew. Chem. , Int. Ed. Engl. 1997, 36, 2402.
10. (a) Polyakov, O. G. ; Ivanova, S. M. ; Gaudinski, C. M. ; Miller, S. M. ; Anderson, O. P. ; Strauss, S. H. Organometallics 1999, 18, 3769.
11. (b) Luppinetti, A. J. ; Strauss, S. H. Chemtracts-Inorg. Chem. 1998, 11, 565.
12. Hurlburt, P. K. ; Rack, J. J. ; Luck, J. S. ; Dec, S. F. ; Webb, J. D. ; Anderson, O. P. ; Strauss, S. H. J. Am. Chem. Soc. 1994, 776, 10003.
13. Xu, Q. ; Souma, Y. ; Heaton, B. T. ; Jacob, C. ; Kanamori, K. Angew. Chem. , Int. Ed. Engl. 2000, 39, 208.
14. For a recent review, see: Xu, Q. ; Souma, Y. Top. Catal. 1998, 6, 17.
15. (a) Souma, Y. ; Sano, H. Bull. Chem. Soc. Jpn. 1976, 49, 3296.
16. (b) Souma, Y. ; Sano, H. J. Org. Chem. 1973, 38, 3633.
17. Souma, Y. ; Sano, H. ; lyoda, J. J. Org. Chem. 1973, 38, 2016.
18. (a) Xu, Q. ; Souma, Y. ; Umezawa, J. ; Tanaka, M. ; Nakatani, H. J. Org. Chem. 1999, 64, 6306.
19. (b) Xu, Q. ; Imamura, Y. ; Fujiwara, M. ; Souma, Y. J. Org. Chem. 1997, 62, 1594.
20. Weber, L. ; Barimeyer, M. ; Quasdorff, J. -M. ; Sievers, H. L. ; Stammler, H. -G. ; Neumann, B. Organometallics 1999, 18, 2497.
21. (a) Nugent, W. A. ; RajanBabu, T. V. ; Burk, M. J. Science 1993, 259, 479.
22. (b) Knowles, W. S. Ace. Chem. Res. 1983, 16, 106.
23. McQuillan, J. F. Homogeneous Hydrogénation in Organic Chemistry; Reidel: 1976.
24. O'Connor, C. ; Wilkinson, G. J. Chem. Soc. A 1968, 2665.
25. (e) Osborn, J. A. ; Jardine, F. H. ; Young, J. F. ; Wilkinson, G. J. Chem. Soc. A 1966, 1711.
26. Bach, C. Ph. D. Thesis, Hannover, 1999.
27. Lupinetti, A. J. ; Havighurst, M. D. ; Miller, S. M. ; Anderson, O. P. ; Strauss, S. H. Submitted for publication.
28. (a) Brewer, S. A. ; Holloway, J. H. ; Hope, E. G. J. Fluorine Chem. 1995, 70, 167.
29. (b) Knight, J. ; Mays, M. J. J. Chem. Soc. A 1970, 711.
30. Knight, J. ; Mays, M. J. Chem. Commun. 1969, 384.
31. (a) Albano, V. G. ; Braga, D. ; Chini, P. ; Strumolo, D. ; Martinengo, S. J. Chem. Soc. , Dalton Trans. 1983, 249.
32. (b) Heaton, B. T. ; Strona, L. ; Martinengo, S. ; Strumolo, D. ; Goodfellow, R. J. ; Sadler, I. H. J. Chem. Soc. , Dalton Trans. 1982, 1499.
33. Chini, P. J. Organomet. Chem. 1980, 200, 37.
34. Malatesta, L. ; Caglio, G. ; Angoletta, M. Chem. Commun. 1970, 532.
35. (a) Ogasawara, M. ; Macgregor, S. A. ; Streib, W. E. ; Foiling, K. ; Eisenstein, O. ; Caulton, K. G. J. Am. Chem. Soc. 1995, 117, 8869.
36. (b) Haefner, S. C. ; Dunbar, K. R. ; Bender, C. J. Am. Chem. Soc. 1991, 113, 9540.
37. Souraa, Y. ; lyoda, J. ; Sano, H. Inorg. Chem. 1976, 15, 968.
38. (a) Brown, C. K. ; Wilkinson, G. J. Chem. Soc. A 1970, 2753.
39. (b) Brown, C. K; Wilkinson, G. Tetrahedron Lett. 1969, 1725.
40. Evans, D. ; Osborn, J. A. ; Wilkinson, G. J. Chem. Soc. A 1968, 3133.
41. (a) Wender, I. ; Pino, P. Organic Synthesis via Metal Carbonyls; Wiley: New York, 1977; Vol. 2.
42. (b) Hjortkjaer, J. ; Jensen, O. R. Ind. Eng. Chem. , Prod. Res. Dev. 1977, 16, 281.
43. Fujimoto, K. ; Tanemura, S. ; Kunugi, T. Nippon Kagaku Kaishi 1977, 2, 167.
44. Hjortkjaer, J. ; Jensen, V. W. Ind. Eng. Chem. , Prod. Res. Dev. 1976, 15, 46.
45. Koch, H. Brennst. Chem. 1955, 35, 321.
46. (a) Olah, G. A. Friedel-Crafts and Related Reaction; WileyInterscience: New York, 1964.
47. (b) Olah, G. A. ; Prakash, G. K. S. ; Sommer, J. Superacids; Wiley-Interscience: New York, 1985.
48. (a) Olah, G. A. ; Bukala, J. J. Org. Chem. 1990, 55, 4293.
49. (b) Bagno, A. ; Bukala, J. ; Olah, G. A. J. Org. Chem. 1990, 55, 4284.
50. (a) Tanaka, M. ; Fujiwara, M. ; Xu, Q. ; Souma, Y. ; Ando, H. ; Laali, K. K. J. Am. Chem. Soc. 1997, 119, 5100.
51. (b) Tanaka, M. ; lyoda, J. ; Souma, Y. 7. Org. Chem. 1992, 57, 2677.
52. Olah, G. A. In Stable Carbocation Chemistry; Prakash, G. K S. , Schleyer, P. v. R. , Eds. ; Wiley-Interscience: New York, 1997; Chapter 1.