PdCl2-catalyzed reduction of organic halides by triethylsilane

Organometallics

Volumn 15, Issue 5, 1996, Pages 1508-1510

  Boukherroub, R ^a,b   Chatgilialoglu, C ^a   Manuel, G ^b  

^a CNR   (Italy)

^b UNIVERSITÉ PAUL SABATIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000802385     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950514k     Document Type: Article

References (30)

1. Imamoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 8, pp 793-809.
2. Chatgilialoglu, C.; Ferreri, C.; Lucarini, M. J. Org. Chem. 1993, 58, 249.
3. Larson, G. L. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; Vol. 1, Chapter 11.
4. (a) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
5. (b) Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229 and references cited therein.
6. (a) Keinan, E.; Greenspoon, N. J. Am. Chem. Soc. 1986, 108, 7314.
7. (b) Perez, D.; Greenspoon, N.; Keinan, E. J. Org. Chem. 1987, 52, 5570.
8. (c) Keinan, E. Pure Appl. Chem. 1989, 61, 1737.
9. (a) Berk, S. C.; Buchwald, S. L. J. Org. Chem. 1992, 57, 3751.
10. (b) Barr, K. J.; Berk, S. C.; Buchwald, S. L. J. Org. Chem. 1994, 59, 4323.
11. (c) Breeden, S. W.; Lawrence, N. J. Synlett 1994, 833.
12. Whitemore, F. C.; Pietrusza, E. W.; Sommer, L. H. J. Am. Chem. Soc. 1947, 69, 2108.
13. Doyle, M. P.; McOsker, C. C.; West, C. T. J. Org. Chem. 1976, 41, 1393.
14. (a) Sommer, L. H.; Citron, J. D. J. Org. Chem. 1967, 32, 2470.
15. (b) Citron, J. D.; Lyons, J. E.; Sommer, L. H. J. Org. Chem. 1969, 34, 638.
16. (a) Nagai, Y.; Matsumoto, H.; Yagihara, T.; Moxishita, K. Kogyo Kagaku Zasshi 1968, 71, 1112.
17. (b) Seyferth, D.; Prud'homme, C. C.; Wang, W. L. J. Organomet. Chem. 1984, 277, 203.
18. (c) Corey, J. Y.; John, C. S.; Ohmsted, M. C.; Chang, L. S. J. Organomet. Chem. 1986, 304, 93.
19. (d) Igarashi, Y.; Kabe, Y.; Hagiwara, T.; Ando, W. Tetrahedron 1992, 48, 89.
20. (e) Boukherroub, R.; Dejean, V.; Manuel, G.; Weber, W. P. Main Group Met. Chem. 1994, 17, 8.
21. Kunai, A.; Sakurai, T.; Toyoda, E.; Ishikawa, M.; Yamamoto, Y. Organometallics 1994, 13, 3233.
22. Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347.
23. (a) Augé, J.; David, S. Carbohydr. Res. 1977, 59, 255.
24. (b) Praly, J.-P. Tetrahedron Lett. 1983, 24, 3075.
25. 3SnH the direct reduction product is accompanied by 1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranose via a reductive rearrangement (see: Giese, B.; Gröninger, K. S. Org. Synth. 1990, 69, 66 and references cited therein).
26. For example, see: (a) Kramer, A. V.; Labinger, J. A.; Bradley, J. S.; Osborn, J. A. J. Am. Chem. Soc. 1974, 96, 7145. (b) Kramer, A. V.; Osborn, J. A. J. Am. Chem. Soc. 1974, 96, 7832.
27. For example, see: (a) Kramer, A. V.; Labinger, J. A.; Bradley, J. S.; Osborn, J. A. J. Am. Chem. Soc. 1974, 96, 7145. (b) Kramer, A. V.; Osborn, J. A. J. Am. Chem. Soc. 1974, 96, 7832.
28. Newcomb, M. Tetrahedron 1993, 49, 1151.
29. Bickelhaupt, F. M.; Ziegler, T.; Schleyer, P. v. R. Organometallics 1995, 14, 2288 and references therein.
30. Fainberg, A. H.; Winstein, J. J. Am. Chem. Soc. 1956, 78, 2763.