Pd-catalyzed silicon hydride reductions of aromatic and aliphatic nitro groups

Organic Letters

Volumn 7, Issue 22, 2005, Pages 5087-5090

  Rahaim Jr , Ronald J ^a   Maleczka Jr , Robert E ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; HYDROCARBON; NITRO DERIVATIVE; PALLADIUM; POLYMETHYLHYDROSILOXANE; SILANE DERIVATIVE; SILOXANE; TRIETHYLSILANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

CATALYSIS; HYDROCARBONS; HYDROCARBONS, AROMATIC; MOLECULAR STRUCTURE; NITRO COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM; SILANES; SILOXANES;

EID: 27644596403     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052120n     Document Type: Article

References (35)

1. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
2. Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanisms; Feuer, H., Ed.; VCH: New York, 1989.
3. (a) Evans, D. A.; Seidel, D. J. Am. Chem. Soc. 2005, 127, 9958-9959.
4. (b) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119-125.
5. (c) Ishii, T.; Fujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558-9559.
6. (d) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423-2425.
7. (a) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692-12693.
8. (b) Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett. 2002, 4, 2621-2623.
9. (c) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388-7389.
10. (a) Kabalka, G. W.; Varma, R. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ed.; Pergamon: Oxford, 1991; Vol. 8, pp 363-379.
11. (b) Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparation, 2nd ed.; Wiley-VCH: New York, 1999; pp 821-828.
12. (a) Adams, J. P. J. Chem. Soc., Perkin Trans. 1 2002, 2586-2597.
13. (b) Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035-2052.
14. For selected examples of newly developed nitro reductions being employed by others, see: (a) Jacobsen, M. F.; Moses, J. E.; Adlington, R. M.; Baldwin, J. E. Org. Lett. 2005, 7, 641-644.
15. (b) Camerei, F.; Ulrich, G.; Ziessel, R. Org. Lett. 2004, 6, 4171-4174.
16. (c) Berque-Bestel, I.; Soulier, J.-L.; Giner, M.; Rivail, L.; Langlois, M.; Sicsic, S. J. Med. Chem. 2003, 46, 2606-2620.
17. (a) Vorbrüggen, H. Silicon-mediated Transformations of Functional Groups, Wiley-VCH: New York, 2004.
18. (b) The Chemistry of Organic Silicon Compounds Parts 1 & 2; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989.
19. (c) Nagai, Y. Org. Prep. Proced. Int. 1980, 12, 13-48.
20. (a) Andrianov, K. A.; Sidorov, V. I.; Filimonova, M. I. Zh. Obshch. Khim. 1977, 47, 485.
21. (b) Andrianov, K. A.; Tartakovskaya, L. M.; Shapiro, B. I. Zh. Obshch. Khim. 1972, 42, 176-180.
22. (c) Andrianov, K. A.; Sidorov, V. I.; Tartakovskaya, L. M.; Anpilogova, A. I.; Nepomnina, V. V.; Pushchevaya, K. S. Dokl. Akad. Nauk. 1970, 195, 352-355.
23. Lipowitz, J.; Bowman, S. A. J. Org. Chem. 1973, 38, 162-165.
24. Nitro group reductions by tin hydrides generated in situ from PMHS reductions of stannoxanes or alkoxystannanes have been reported: Nitzsche, H. S.; Wick, M. Angew. Chem. 1957, 69, 96.
25. For reviews of PMHS as a reagent for organic synthesis, see: (a) Lawrence, N. J.; Drew, M. D.; Bushell, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 3381-3391.
26. (b) Lavis, J. M.; Maleczka, R. E., Jr. Polymethylhydrosiloxane (PMHS). In eEROS-Electronic Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Crich, D., Fuchs, P. L., Wipf, P., Eds.; Wiley: New York 2003; [Online].
27. Brinkman, H. R.; Miles, W. H.; Hilborn, M. D.; Smith, M. C. Synth. Commun. 1996, 26, 973-980.
28. Rahaim, R. J., Jr.; Maleczka, R. E., Jr. Tetrahedron Lett. 2002, 43, 8823-8826.
29. th Organosilicon Symposium, Philadelphia, PA, May 20-22, 2004; Poster P-34.
30. 2, Poly(methyl-hydrosiloxane), and Aqueous KF. Presented at the 37th Organosilicon Symposium, Philadelphia, PA, May 20-22, 2004; Poster P-35.
31. (a) Chauhan, B. P. S.; Rathore, J. S.; Bandoo, T. J. Am. Chem. Soc. 2004, 126, 8493-8500.
32. For related observations see: (b) Fowely, L. A.; Michos, D.; Luo, X.-L.; Crabtree, R. H. Tetrahedron Lett. 1993, 34, 3075-3078.
33. (c) Tour, J. M.; Pendalwar, S. L.; Cooper, J. P. Chem. Mater. 1990, 2, 647-649.
34. Yactine, B.; Ganachaud, F.; Senhaji, O.; Boutevin, B. Macromolecules 2005, 38, 2230-2236.
35. Zschiesche, R.; Reissig, H.-U. Tetrahedron Lett. 1988, 65, 1685-1686.