Facile reduction of carboxylic acids, esters, acid chlorides, amides and nitriles to alcohols or amines using NaBH4/BF3· Et2O

Bulletin of the Korean Chemical Society

Volumn 25, Issue 3, 2004, Pages 407-409

  Cho, Su Dong ^b   Park, Yong Dae ^a   Kim, Jeum Jong ^a   Falck, J R ^c   Yoon, Yong Jin ^a  

^a Gyeongsang National University   (South Korea)

^b Changwon National University   (South Korea)

^c UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

Acid chloride; Amide; Ester; NaBH4 BF3 Et2O; Nitrile; Reduction of carboxylic acid

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; AMINE; BORANE DERIVATIVE; BORON TRIFLUORIDE ETHERATE; CARBOXYLIC ACID; CHLORIDE; ETHANE; FLUORIDE; NITRILE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION;

EID: 3042585348     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2004.25.3.407     Document Type: Article

References (41)

1. Walker, J. Chem. Soc. Rev. 1976, 5, 23.
2. Brown, H. C.; Heim, P.; Yoon, N. M. J. Am. Chem. Soc. 1970, 92, 1637.
3. Yoon, N. M.; Pak, C. S.; Brown, H. C.; Krishnamurthy, S.; Stocky, T. P. J. Org. Chem. 1973, 38, 2786.
4. Cho, B. T.; Yoon, N. M. Synth. Commun. 1985, 15, 917.
5. Das, J.; Chandrasekharan, S. Synth. Commun. 1990, 20, 907.
6. Brown, H. C.; Weissman, P. M.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1458.
7. Brown, H. C.; Weissman, P. M. J. Am. Chem. Soc. 1956, 78, 6714.
8. Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1956, 78, 2582.
9. Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1960, 82, 681.
10. Kano, S.; Tanaka, Y.; Sugino, E.; Hibino, S. Synthesis 1980, 695.
11. Lane, C. F.; Myatt, H. L.; Daniels, J.; Hopps, H. B. J. Org. Chem. 1974, 39, 3052.
12. Smith, G. A.; Gawley, R. E. Org. Syn. 1984, 63, 136.
13. Paquette, L. A. Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: New York, 1995; Vol 7, pp 4522-4528.
14. Periasamy, M.; Thirumalaikumar, M. J. Organometal. Chem. 2000, 609, 137.
15. Ward, D. E.; Rhee, C. K. Canadian J. Chem. 1989, 67, 1206.
16. Brown, H. C.; Narasimhan, S.; Choi, Y. M. J. Org. Chem. 1982, 47, 4702.
17. Yamakawa, T.; Masaki, M.; Nohira, H. Bull. Chem. Soc. Jpn. 1991, 64, 2730.
18. Yoo, S.; Lee, S. Synlett. 1990, 419.
19. Prasad, A. S. B.; Kanth, J. V. B.; Periasamy, M. Tetrahedron 1992, 48, 4623.
20. Saito, S.; Ishikawa, T.; Kuroda, A.; Koga, K.; Moriwake, T. Tetrahedron 1992, 48, 4067.
21. Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517.
22. Suseela, Y.; Periasamy, M. Tetrahedron 1992, 48, 371.
23. Lalancette, J. M.; Freche, A.; brindle, J. R.; Laliberte, M. Synthesis 1972, 526.
24. Itsuno, S.; Sakurai, Y.; Ito, K. Synthesis 1988, 995.
25. Akabori, S.; Takanohashi, Y. J. Chem. Soc. Perkin Trans. I 1991, 479.
26. Wann, S. R.; Thorsen, P. T.; Kreevoy, M. M. J. Org. Chem. 1981, 46, 2579.
27. Giannis, A.; Sandhoff, K. Angew. Chem. Int. Ed. Engl. 1989, 28, 218.
28. Ono, A.; Hayakawa, H. Chem. Lett. 1987, 853.
29. Fujii, H.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1991, 32, 6147.
30. Komiya, S.; Tsutsumi, O. Bull. Chem. Soc. Jpn. 1987, 60, 3423.
31. Caycho, J, R.; Tellado, F. G.; de Armas, P.; Tellado, J. J. M. Tetrahdron Lett. 1997, 38, 277.
32. Santaniello, E.; Poni, F.; Anzocchi, A. Synthesis 1978, 891.
33. Bianchi, G.; Achilli, F.; Gamba, A.; Vercesi, D. J. Chem. Soc. Perkin Trans. 1 1988, 417.
34. Yatagai, M.; Ohnuki, T. J. Chem. Soc. Perkin Trans. 1 1990, 1826.
35. Nagata, T.; Yorozu, K.; Yamada, T.; Mukiyama, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 2145.
36. Sarker, A.; Rao, B. R. Tetrahedron Lett. 1991, 32, 1247.
37. Okawa, H.; Katsuki, T.; Nakamura, M.; Kumagai, N.; Shuin, Y.; Shinmyozu, T; Kida, S. J. Chem. Soc. Chem. Commun. 1989, 139.
38. Sarkar, A.; Aao, B. R.; Bhattacharya, P. K. Indian J. Chem. 1995, 34B, 156.
39. Gribble, G. W.; Jasinski, J. M.; Pellicone, J. T.; Panetta, J. A. Synthesis 1978, 766.
40. Tale, R. H.; Patil, K. M.; Dapurkar, S. E. Tetrahedron Lett. 2003, 44, 3427.
41. Pettit, G. R.; Piatak, D. M. J. Org. Chem. 1962, 27, 2127.