Transition-metal-based Lewis acid, base, and ambiphilic catalysts: Development of non-salt alternative processes

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 61, Issue 5, 2003, Pages 425-435

  Murahashi, Shun Ichi ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Acid and base ambiphilic catalyst; C H activation; Combinatorial chemistry; Green chemistry; Heteroatom effect; Low salt alternatives; Polyamides; Redox base catalyst; Redox Lewis acid catalyst

Indexed keywords

ATOMS; CATALYSTS; CHEMICAL ACTIVATION; HYDROGEN BONDS; IRIDIUM; RHENIUM COMPOUNDS; RHODIUM; RUTHENIUM; SUBSTRATES;

AMPHIPHILIC CATALYSTS; CARBONYL COMPOUNDS; GREEN CHEMISTRY; ISOCYANATES; LEWIS ACID; NITRILES; NON SALT ALTERNATIVE PROCESSES; REDOX BASE CATALYSTS; RHENIUM HYDRIDE COMPLEXES;

CATALYSIS;

EID: 0043245984     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.61.425     Document Type: Article

References (73)

1. P. T. Anastas, J. C. Warner, Green Chemistry, Theory and Practice, Oxford University Press, Oxford, 1998
2. S.-I. Murashani, Angew. Chem., Int. Ed. Engl., 34, 2443 (1995)
3. B. M. Trost, Science, 254, 1471 (1991)
4. B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995)
5. R. A. Sheldon, Chem. Ind., 1997, 12
6. R. A. Sheldon, J. Chem. Tech. Biotechnol., 68, 381 (1997)
7. S.-I. Murahashi, T. Naota, Chemtracks.-Org. Chem., 7, 281 (1994)
8. S.-I. Murahashi, T. Naota, Bull. Chem. Soc. Jpn., 69, 1 (1996)
9. T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev., 98, 2599 (1998)
10. S.-I. Murahashi, H. Takaya, Acc. Chem. Res., 33, 225 (2000)
11. S.-I. Murahashi, H. Takaya, Pure. Appl. Chem., 74, 19 (2002)
12. G. W. Grible, Acc. Chem. Res., 31, 141 (1998)
13. (a) R. H. Crabtree, Chem. Rev., 85, 245 (1985)
14. (b) B. A. Anderson, R. G. Bergman, T. Mobley, T. H. Peterson, Acc. Chem. Res., 28, 154 (1995)
15. (c) A. E. Shilov, G. B. Shulpin, Chem. Rev. 97, 2879 (1997)
16. (d) S. Murahashi, J. Am. Chem. Soc., 77, 6403 (1955)
17. (a) S.-I. Murahashi Pure Appl. Chem., 64, 403 (1992)
18. (b) S.-I. Murahashi, N. Kojima, "Biomimetic Oxidations" Ed. B. Munier, Imperial College Press, London, pp 561-611 (1999)
19. S.-I. Murahashi, T. Hirano, T. Yano, J. Am. Chem. Soc., 100, 348 (1978)
20. R. M. Laine, D. W. Thomas, L. W. Cary, S. E. Buttrill, J. Am. Chem. Soc., 100, 6527 (1978)
21. S.-I. Murahashi, T. Watanabe, J. Am. Chem. Soc., 101, 7429 (1979)
22. S. Inoue, H. Takaya, K. Tani, S. Otsuka, T. Sato, R. Noyori, J. Am. Chem. Soc., 112, 4897 (1990)
23. N. Chatani, T. Asami, T. Kuroda, S. Yorimitu, Y. Ishii, Y. Kakiuchi, S. Murai, J. Am. Chem. Soc., 122, 12882 (2000)
24. T. Naota, H. Taki, M. Mizuno, S.-I. Murahashi, J. Am. Chem. Soc., 111, 59 54 (1989)
25. S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano, A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995)
26. S. Komiya, Y. Mizuho, N. Kasuga, Chem. Lett., 1991, 2127
27. S.-I. Murahashi, T. Take, T. Naota, H. Takaya, Synlett, 2000, 1016
28. Y. Lin, X. Zhu, M. Xiang, J. Organomet. Chem., 448, 215 (1993)
29. M. Mirano, M. Hirai, Y. Ito, T. Tsurumaki, A. Baba, A. Fukuoka, S. Komiya, J. Organomet. Chem., 569, 3 (1998)
30. Y. Yamamoto, M. AlMasum, N. Asao, J. Am. Chem. Soc., 116, 6019 (1994)
31. B. M. Trost, V. J. Gerusz, J. Am. Chem. Soc., 117, 5156 (1995)
32. (a) S.-I. Murahashi, T. Naota, M. Maezaki, the 61th Annual Meetings of the Chemical Society of Japan, Yokohama, March 29-April 1, 1991, Abstracts 1 C 940
33. (b) S. Paganelli, A. Schionato, C. Botteghi, Tetrahedron Lett., 32, 2807 (1991)
34. Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao, H. Nemoto, J. Am. Chem. Soc., 116, 3161 (1994)
35. M. Sawamura, H. Hamashima, Y. Ito, J. Am. Chem. Soc., 114, 8295 (1992)
36. K. Inagaki, K. Nozaki, H. Takaya, Synlett, 1997, 119
37. T. Naota, A. Tannna, S.-I. Murahashi, J. Am. Chem. Soc., 122, 2960 (2000)
38. T. Naota, A. Tannna, S.-I. Murahashi, Chem. Commun., 2001, 63
39. T. Naota, A. Tannna, S. Kamuro, S.-I. Murahashi, J. Am. Chem. Soc., 124, 6842 (2002)
40. S.-I. Murahashi, T. Naota, Y. Nakano, 93th Symposium on Organometallic Chem. Jp., 1996, Abstract, p 310
41. J. G. Stack, J. J. Doney, R. G. Bergman, C. H. Heathcock, Organometallics, 9, 453 (1990)
42. S.-I. Murahashi, T. Naota, H. Takaya, X. Zhou, unpublished results
43. S. G. Alvarez, S. Hasegawa, M. Hirano, S. Komiya, Tetrahedron Lett., 39, 5290 (1998)
44. E. Gómez-Bengoa, J. M. Cuerva, C. Mateo, A. M. Echavarren, J. Am. Chem. Soc., 118, 8553 (1996)
45. S.-I. Murahashi, H. Takaya M. Itoh, 47th Symposium on Organometallic Chem. Jp, 2000, Abstract, p 308
46. S. M. Hannick, Y. Kishi, J. Org. Chem., 48, 3833 (1983)
47. H. Takaya, S. Kojima, S.-I. Murahashi, Org. Lett., 3, 421 (2001)
48. (a) B. Bosnich, Aldrichimica Acta, 31, 76 (1998)
49. (b) W. Odenkirk, A. L. Rheingold, B. Bosnich, J. A. Chem. Soc., 114, 6392 (1992)
50. (c) J. M. Faller, Y. Ma. Tetrahedron Lett., 30, 1189 (1989)
51. (d) E. P. Kundig, C. M. Saudan, G. A. Bernardinelli, Angew. Chem., Int. Ed., 38, 1220 (1999)
52. S.-I. Murahashi, T. Naota, E. Saito, J. Am. Chem. Soc., 108, 7846 (1986)
53. S.-I. Murahashi, S. Sasao, E. Saito, T. Naota, J. Org. Chem., 57, 2521 (1992)
54. T. Naota, S. Sasao, K. Tanaka, H. Yamamoto, S.-I. Murahashi, Tetrahedron Lett., 34, 4843 (1993)
55. S.-I. Murahashi, S. Sasao, E. Saito, T. Naota, Tetrahedron. 49, 8805 (1993)
56. Betty, R. P. WO 9623753
57. H. Yamada, M. Kobayashi, Biosci. Biotechnol. Biochem., 60, 1391 (1996)
58. W. Huang, J. Jia, J. Cummings, M. Nelson, G. Shneider, Y Lindqvist, Structure, 5, 691 (1997)
59. T. Naota, Y. Shichijo, S.-I. Murahashi, J. Chem. Soc., Chem. Commun., 1994, 1359
60. R. Adams, A. F. Thal, Org. Syn. Coll., 1, 270 (1956)
61. (a) S.-I. Murahashi, K. Ito, T. Naota, Y. Maeda, Tetrahedron Lett., 22, 5327 (1981)
62. (b) S.-I. Murahashi, K. Ito, T. Naota, Y. Maeda, H. Taki, J. Org. Chem., 52, 4319 (1987)
63. S.-I. Murahashi, T. Naota, E. Saito, J. Am. Chem. Soc., 108, 7846 (1986)
64. G. W. Parshall, S. D. Ittel, Homogeneous Catalysis, 2nd Ed., Wiley, New York, 42 (1980)
65. G. Achhammer, P. Basler, R. Fischer, E. Fuchs, H. Luyken, W. Schnurr, G. Voit, L. Hilprecht, DE 19548289
66. D. A. O'Sullivan, Chem. Eng. News, March 3, 21 (1986)
67. H. Takaya, T. Naota, S.-I. Murahashi, J. Am. Chem. Soc., 120, 4244 (1998)
68. H. Takaya, K. Yoshida, K. Isozaki, S.-I. Murahashi, 48th Symposium on Organometallic Chem. Jp. 2001, Abstract p 338
69. R. W. Hartmann, J. Med. Chem., 29, 1362 (1986)
70. H. Takaya, S.-I. Murahashi, Synlett, 2001, 991