Activation of manganese metal with a catalytic amount of lead and Me3SiCl and its application to organic synthesis

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 60, Issue 11 SPEC., 2002, Pages 1055-1062

  Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL ACTIVATION; ESTERS; FREE RADICALS; IODINE COMPOUNDS; LEAD COMPOUNDS; OLEFINS; REDUCTION; SILICON COMPOUNDS; X RAY PHOTOELECTRON SPECTROSCOPY;

ALKENYLSILANE; ALKYL IODIDE; ALKYL RADICAL; CARBONYL YLIDE; ELECTRON-DEFICIENT OLEFIN; REDUCTANT;

MANGANESE;

EID: 0036880141     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.60.1055     Document Type: Article

References (63)

1. (a) Hiyama, T.; Sawahata, M.; Obayashi, M. Chem. Lett. 1983, 1237
2. Hiyama, T.; Sawahata, M.; Obayashi, M. Nippon Kagakukaishi 1984, 1022.
3. (b) Cahiez, G.; Chavant, P. Y. Tetrahedron Lett. 1989, 30, 7373.
4. Highly activated Mn powder was prepared by reduction of manganese salts with lithium napthalenide. (a) Kim, S. H.; Hanson, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197
5. Rieke, R. D.; Kim, S.-H. J. Org. Chem. 1998, 63, 5235
6. Rieke, R. D. Aldrichimica Acta 2000, 33, 52.
7. 8K, see: Fürstner, A.; Brunner, H Tetrahedron Lett. 1996, 37, 7009.
8. (a) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533; 12349.
9. (b) Boeckman, R. K., Jr.; Hudack, R. A., Jr. J. Org. Chem. 1998, 63, 3524.
10. (c) Savatoš, A.; Boland, W. Synlett 1998, 549.
11. (d) Bandini, M.; Cozzi, P.C.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 1999, 38, 3357.
12. (e) Hari, A.; Karan, C.; Rodrigues, W. C.; Miller, B. L. J. Org. Chem. 2001, 66, 991.
13. (a) Mn-Ti: Green, M. L. H.; Lucas, C. R. J. Chem. Soc., Dalton Trans. 1972, 1000.
14. Coutts, R. S. P.; Wailes, P. C.; Martin, R. L. J. Organomet. Chem. 1973, 47, 375
15. Sekutowski, D.; Jungst, R.; Stucky, G. D. Inorg. Chem. 1978, 17, 1848
16. Stephan, D. W. Organometallics 1992, 11, 996.
17. (b) Gansaüer, A.; Bauer, D. J. Org. Chem. 1998, 63, 2070
18. Gansaüer, A.; Pierobon, M.; Bluhm, H. Angew. Chem., Int. Ed. 1998, 37, 101.
19. (c) Dunlap, M. S.; Nicholas, K. M. Synth. Commun. 1999, 27, 1097.
20. (d) Parrish, J. D.; Little, R. D. Org. Lett. 2002, 4, 1439.
21. (e) Mn-Cu: Li, C-J.; Meng, Y.; Yi, X.-H.; Ma, J.; Chan, T. H. J. Org. Chem. 1998, 63, 7498.
22. Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37 7049.
23. (a) Gaudemar, M. Bull. Soc. Chim. Fr. 1962, 974.
24. (b) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
25. (c) Takai, K.; Kakiuchi, T.; Utimoto, K. J. Org. Chem. 1994, 59, 2671.
26. (a) Takai, K.; Ikawa, Y. Org. Lett. 2002, 4, 1727.
27. (b) Tanaka, H.; Yamashita, S.; Ikemoto, Y.; Torii, S. Chem. Lett. 1987, 673.
28. Wender, P. A. (Ed.) Chem. Rev. 1996, 96 (1 & 2) "Frontiers in Organic Synthesis."
29. For some representative examples, see: (a) Cr: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732.
30. (b) Sm: Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439.
31. Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872
32. Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050
33. Curran, D. P.; Fevig, T. L.: Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943
34. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
35. (c) Zn: Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
36. Takai, K.; Ueda, T.; Ikeda, N.; Moriwake, T. J. Org. Chem. 1996, 61, 7990.
37. Suzuki, M.; Kawagishi, T.; Suzuki, T.; Noyori, R. Tetrahedron Lett. 1982, 23, 4057.
38. Shono, T.; Nishiguchi, I.; Sasaki, M. J. Am. Chem. Soc. 1978, 100, 4314.
39. Kaihara, H.; Ueda, T.; Takai, K.; Moriwake, T. 70th Annual Meeting of the Chemical Society of Japan, 3J136 (1996).
40. (a) Giese, B.; Lachhein, S. Angew. Chem., Int. Ed. Engl. 1982, 21, 768.
41. (b) Curran, D. P.; Kim, D. Tetrahedron 1991, 47, 6171
42. Curran, D. P.; Kim, D.; Ziegler, C. Tetrahedron 1991, 47, 6189.
43. (c) Lowinger, T. B.; Weiller, L. J. Org. Chem. 1992, 57, 6099.
44. Ueda, T.; Ishiyama, T.; Takai, K.; Moriwake, T. 70th Annual Meeting of the Chemical Society of Japan, 3PB104 (1996).
45. (a) Wittig, G.; Wingler, F. Liebigs Ann. Chem. 1962, 656, 18
46. Wittig, G.; Wingler, F. Chem. Ber. 1964, 97, 2139; 2146
47. (b) Wittig, G.; Jautelat, M. Liebigs Ann. Chem. 1967, 702, 24.
48. (c) Denis, J. M.; Girard, C. Conia, J. M. Synthesis 1972, 549.
49. (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1964, 81, 1640.
50. (b) Corey, E. J.; Jautelat, M. J. Am. Chem. Soc. 1967, 89, 3912.
51. (c) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965. 87, 1353.
52. (d) Truce, W. E.; Badiger, V. V. J. Org. Chem. 1964, 29, 3277.
53. Bassindale, A. R.; Stout, T. Tetrahedron Lett. 1985, 26, 3403.
54. Takai, K.; Ueda, T.; Kaihara, H.; Sunami, F.; Moriwake, T. J. Org. Chem. 1996, 61, 8728.
55. Aoki, Y.; Kuwajima, I. Tetrahedron Lett. 1990, 31, 7457.
56. Takai, K.; Kaihara, H.; Higashiura, K.-i. Ikeda, N. J. Org. Chem. 1997, 62, 8612.
57. Hojo, M.; Aihara, H.; Suginohara, Y.; Sakata, K.; Nakamura, S.; Murakami, C.; Hosomi, A. J. Org. Chem. 1997, 62, 8610.
58. Hojo, M.; Aihara, H.; Hosomi, A. J. Am. Chem. Soc. 1996, 118, 3533.
59. Takai, K.; Hikasa, S.; Ichiguchi, T.; Sumino, N. Synlett 1999, 1769.
60. Concellón, J. M.; Bernard, P. L.; Pérez-Andrés, J. A. Tetrahedron Lett. 1998, 39, 1409.
61. Takai, K.; Ichiguchi, T.; Hikasa, S. Synlett 1999, 1268.
62. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc., 1986, 108, 7408.
63. Tanaka, K.; Yamano, S.; Mitsunobu, O. Synlett 2001, 1620.