Selenium and tellurium chalcogenides as mild and efficient reducing agents for α-halo ketones

Synthesis

Volumn , Issue 8, 1998, Pages 1137-1140

  Schultz, Erwin K V ^a   Harpp, David N ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Chalcogenides; Reductive dehalogenation; Selenium; Tellurium; halo ketones

Indexed keywords

FLUORIDE ION; KETONE DERIVATIVE; REDUCING AGENT; SELENIUM; TELLURIUM;

CONTROLLED STUDY; DEHALOGENATION; DRUG SYNTHESIS; FREEZING; NONHUMAN; SHORT SURVEY; SYNTHESIS;

EID: 0031849498     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2130     Document Type: Short Survey

References (53)

1. 4-heavy metal salts: Goto, T.; Kishi, Y. Tetrahedron Lett. 1961, 513.
2. Phosphines: Borowitz, I. J.; Grossman, L. I. Tetrahedron Lett. 1962, 471.
3. Hoffmann, H.; Diehr, H. J. Tetrahedron Lett. 1962, 583.
4. Borowitz, I. J.; Virkhaus, R. J. Am. Chem. Soc. 1963, 55, 2183.
5. Borowitz, I. J.; Kirby, K. C., Jr.; Virkhaus, R. J. Org. Chem. 1966, 31, 4031.
6. Borowitz, I. J.; Kirby, K. C., Jr.; Rusek, P. E.; Lord, E. J. Org. Chem. 1969, 34, 2687.
7. Organotin hydrides: Kuivila, H. G.; Menapace, L. W. J. Org. Chem. 1963, 28, 2165.
8. N,N-Dimethylaniline: Giumanini, A. G. Chimia 1967, 21, 464.
9. Zn/HOAc: Sauers, R. R.; Hu, C. K. J. Org. Chem. 1971, 36, 1153.
10. 2O-Lil: Townsend, J. M.; Spencer, T. A. Tetrahedron Lett. 1971, 137.
11. For a review of reductive dehalogenation of polyhalo ketones, see Noyori, R; Hayakawa, Y. Org. React. 1983, 29, 163.
12. Dubois, J. E.; Lion, C.; Dugast, J. Y. Tetrahedron Lett. 1983, 24, 4207.
13. Ho, T. L.; Wong, C. Synth. Commun. 1973, 3, 237.
14. Gemal, A. L.; Luche, J. L. Tetrahedron Lett. 1980, 21, 3195.
15. Olah, G. A.; Arvanaghi, M.; Vankar, Y. D. J. Org. Chem. 1980, 45, 3531.
16. Ho, T. L. Synth. Commun. 1981, 11, 101.
17. Olah, G. A.; Husain, A.; Sing, B. P.; Mehrotra, A. K. J. Org. Chem. 1983, 48, 3667.
18. Ono, A.; Fujimoto, E.; Ueno, M. Synthesis 1986, 570.
19. Renso, M.; Mottadelli, S.; Albanese, D. Synth. Commun. 1993, 23, 1385.
20. Mandai, A. K.; Nijasure, A. M. Synlett 1990, 554.
21. Akane, N.; Kanagawa, Y.; Nishiyama, Y.; Ishi, Y. Chem. Lett. 1992, 12, 2431.
22. Denis, J. N.; Krief, A. Tetrahedron Lett. 1981, 22, 1431.
23. Osuka, A.; Suzuki, H. Chem. Lett. 1983, 119.
24. Clive, D. L.; Beaulieu, P. L. J. Org. Chem. 1982, 47, 1124.
25. Engman, L.; Cava, M. P. J. Org. Chem. 1982, 47, 3946.
26. Seshadri, R.; Pegg, W. J.; Israel, M. J. Org. Chem. 1981, 46, 2596.
27. Fuji, K.; Node, M.; Kawabata, T.; Fujimoto, M. Chem. Lett. 1984, 1153.
28. Oriyama, T.; Mukaiyama, T. Chem. Lett. 1984, 2069.
29. Ono, A.; Fujimoto, E.; Ueno, M. Synth. Commun. 1986, 16, 653.
30. Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 1135.
31. Fuji, K.; Node, M.; Kawabata, T.; Fujimoto, M. J. Chem. Soc., Perkin Trans. I 1987, 1043.
32. Ono, A.; Maruyama, T.; Kamimura, J. Synthesis 1987, 1093.
33. Ono, A.; Kamimura, J.; Suzuki, N. Synthesis 1987, 406.
34. Borah , H.; Boruah, R. C.; Sandhu, J. S. J. Chem. Soc., Chem. Commun. 1991, 154.
35. Hutchins, R. O.; Kandasamy, D.; Maryanoff, C. A.; Masilamani, D.; Maryanoff, B. J. Org. Chem. 1977, 42, 82.
36. Kim, S.; Kim, Y. J.; Ahn, K. H. Tetrahedron Lett. 1983, 24, 3369.
37. Urata, H.; Suzuki, H.; Moro-Oka, Y.; Ikawa, T. J. Organomet. Chem. 1982, 234, 367.
38. Perez, D.; Greenspoon, N.; Keinan, E. J. Org. Chem. 1987, 52, 5570.
39. Ho, T. L.; Pattee, L. J. Org. Chem. 1974, 39, 562.
40. Chung, S. K.; Hu, Q. Y. Synth. Commun. 1982, 12, 261.
41. Sarma, J. C.; Borbaruah, M.; Sharma, R. P. Tetrahedron Lett. 1985, 26, 4657.
42. Alper, H.; Logbo, K. D.; des Abbayes, H. Tetrahedron Lett. 1977, 2861.
43. Alper, H.; Pattee, L. J. Org. Chem. 1979, 44, 2568.
44. Luh, T. Y.; Lai, C. H.; Lei, K. H.; Tam, S. W. J. Org. Chem. 1979, 44, 641.
45. Li, C. L.; Harpp, D. N. Tetrahedron Lett. 1991, 32, 1545.
46. Einstein, F. W. B.; Jones, C. H. W.; Jones, T.; Sharma, R. D. Can. J. Chem. 1983, 61, 2611.
47. Schumann, H.; Thom, K. F.; Schmidt, M. J. Organomet. Chem. 1964, 2, 361.
48. Detty, M. R.; Seidler, M. D. J. Org. Chem. 1982, 47, 1354.
49. Li, C. J. Ph.D. Thesis, McGill University, Montreal, Canada 1991.
50. 21 are consistent with this structural assignment. Additional information was obtained fron an APT (Attached Proton Test) and an isotopic distribution report.
51. 21 are also consistent with this structural assignment.
52. Duddeck, H. Prog. Nucl. Magn. Reson. Spectrosc. 1995, 27, 1.
53. Gingras, M.; Harpp, D. N. J. Am. Chem. Soc. 1988, 110, 7737.