Bu3SnH-Catalyzed Reduction of Nitroalkanes to Alkanes

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5296-5297

  Tormo, Jordi ^a   Hays, David S ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542600377     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980789k     Document Type: Article

References (33)

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3. Based on a search of the Beilstein Crossfire database.
4. For a review, see: Ono, N.; Kaji, A. Synthesis 1986, 693-704. See also: Larock, Richard C. Comprehensive Organic Transformations; VCH: New York, 1989; p 26.
5. For a review, see: Ono, N.; Kaji, A. Synthesis 1986, 693-704. See also: Larock, Richard C. Comprehensive Organic Transformations; VCH: New York, 1989; p 26.
6. For mechanistic studies, see: (a) Dupuis, J.; Giese, B.; Hartung, J.; Leising, M.; Korth, H.-G.; Sustmann, R. J. Am. Chem. Soc. 1985, 707, 4332-4333. Korth, H.-G.; Sustmann, R.; Dupuis, J.; Giese, B. Chem. Ber. 1987, 120, 1197-1202. (b) Kamimura, A.; Ono, N. Bull. Chem. Soc. Jpn. 1988, 61, 3629-3635. (c) Tanner, D. D.; Harrison, D. J.; Chen, J.; Kharrat, A.; Wayner, D. D. M.; Griller, D.; McPhee, D. J. J. Org. Chem. 1990, 55, 3321-3325.
7. For mechanistic studies, see: (a) Dupuis, J.; Giese, B.; Hartung, J.; Leising, M.; Korth, H.-G.; Sustmann, R. J. Am. Chem. Soc. 1985, 707, 4332-4333. Korth, H.-G.; Sustmann, R.; Dupuis, J.; Giese, B. Chem. Ber. 1987, 120, 1197-1202. (b) Kamimura, A.; Ono, N. Bull. Chem. Soc. Jpn. 1988, 61, 3629-3635. (c) Tanner, D. D.; Harrison, D. J.; Chen, J.; Kharrat, A.; Wayner, D. D. M.; Griller, D.; McPhee, D. J. J. Org. Chem. 1990, 55, 3321-3325.
8. For mechanistic studies, see: (a) Dupuis, J.; Giese, B.; Hartung, J.; Leising, M.; Korth, H.-G.; Sustmann, R. J. Am. Chem. Soc. 1985, 707, 4332-4333. Korth, H.-G.; Sustmann, R.; Dupuis, J.; Giese, B. Chem. Ber. 1987, 120, 1197-1202. (b) Kamimura, A.; Ono, N. Bull. Chem. Soc. Jpn. 1988, 61, 3629-3635. (c) Tanner, D. D.; Harrison, D. J.; Chen, J.; Kharrat, A.; Wayner, D. D. M.; Griller, D.; McPhee, D. J. J. Org. Chem. 1990, 55, 3321-3325.
9. For mechanistic studies, see: (a) Dupuis, J.; Giese, B.; Hartung, J.; Leising, M.; Korth, H.-G.; Sustmann, R. J. Am. Chem. Soc. 1985, 707, 4332-4333. Korth, H.-G.; Sustmann, R.; Dupuis, J.; Giese, B. Chem. Ber. 1987, 120, 1197-1202. (b) Kamimura, A.; Ono, N. Bull. Chem. Soc. Jpn. 1988, 61, 3629-3635. (c) Tanner, D. D.; Harrison, D. J.; Chen, J.; Kharrat, A.; Wayner, D. D. M.; Griller, D.; McPhee, D. J. J. Org. Chem. 1990, 55, 3321-3325.
10. For applications of nitroalkanes in organic synthesis, see; Rosini, G.; Ballini, R. Synthesis 1988, 833-847.
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16. (a) Barton-McCombie deoxygenation of alcohols: Lopez, R. M.; Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 6949-6950.
17. (b) Reduction of azides: Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796-2797.
18. (c) Reductive cyclization of enals and enones: Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4-5.
19. (d) Conjugate reduction of enones; Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751-6752.
20. For the work of others, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. Lipowitz, J.; Bowman, S. A. Aldrichim. Acta 1973, 6, 1-6. (b) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
21. For the work of others, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. Lipowitz, J.; Bowman, S. A. Aldrichim. Acta 1973, 6, 1-6. (b) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
22. For the work of others, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. Lipowitz, J.; Bowman, S. A. Aldrichim. Acta 1973, 6, 1-6. (b) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
23. For the work of others, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. Lipowitz, J.; Bowman, S. A. Aldrichim. Acta 1973, 6, 1-6. (b) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
24. (a) Itoi, K. Fr. Patent 1,368,522, 1964. Itoi, K.; Kumano, S. Kogyo Kagaku Zasshi 1967, 70, 82-86.
25. (a) Itoi, K. Fr. Patent 1,368,522, 1964. Itoi, K.; Kumano, S. Kogyo Kagaku Zasshi 1967, 70, 82-86.
26. (b) Hayashi, K; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94.
27. (c) Pijselman, J.; Pereyre, M. J. Organomet. Chem. 1973, 63, 139-157.
28. (d) See also ref 10a.
29. Kobayashi, K.; Kwanisi, M.; Kozima, S. Synth, React. Inorg. Met.-Org. Chem. 1978, 8, 75-82.
30. n-TMS; PMHS) is ineffective for this reduction.
31. 3 (0.061 mL, 0.50 mmol), and 1,1′-azobis(cyclohexanecarbonitrile) (ACHN; 49 mg, 0.20 mmol) in toluene (0.3 mL) was added to a solution of the nitroalkane (1.00 mmol) in toluene (0.2 mL). The resulting mixture was immersed in a 110 °C oil bath and stirred for 5 h. Additional ACHN (49 mg, 0.20 mmol) was then added, and the mixture was stirred for 3 more hours at 110 °C. The reaction product was then purified by flash chromatography.
32. Reductions can be achieved with lower catalyst loadings, but longer reaction times are required. The use of smaller amounts of initiator sometimes leads to incomplete reduction.
33. 2).