Sonochemical, aerobic conversion of alkyl halides into alcohols promoted by trialkyltin halide/NaBH3CN catalytic system

Chemistry Letters

Volumn , Issue 8, 1997, Pages 705-706

  Sawamura, Masaya ^a   Kawaguchi, Yasuhide ^a   Sato, Kenichi ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031490829     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.705     Document Type: Article

References (13)

1. E. Nakamura, T. Inubushi, S. Aoki,and D Machii, J. Am. Chem. Soc., 113, 8980 (1991).
2. For an example of radical-mediated halide-to-alcohol conversion, see: A. G. Barrett and D. J. Rys, J. Chem. Soc., Chem. Commun., 1994, 837.
3. For our previous studies on sonochemistry, see: a) E. Nakamura, D. Machii and T. Inubushi, J. Am. Chem. Soc., 111, 6849 (1989).
4. b) E. Nakamura, Y. Imanishi and D. Machii, J. Org. Chem., 59, 8178 (1994), and references cited therein.
5. A part of this work has been orally communicated at the 68th annual meeting of the Chemical Society of Japan, Kyoto (1995).
6. For catalytic radical dehalogenation, see: a) H. Kuivila and L. W. Menapace, J. Org. Chem., 28, 2165 (1963).
7. b) E. J. Corey and J. W. Suggs, J. Org. Chem., 40, 2554 (1975).
8. 2. See: A. G. Davis, B. Muggleton, B. P. Robert, M. W. Tse and J. N. Winter, J. Organometal. Chem., 118, 289 (1976).
9. a) G. V. Koten, C. A. Schaap, and J. G. Noltes, J. Organomet. Chem, 99, 157 (1975).
10. b) E. Vedejs, S. M. Duncan and A. R. Haighl, J Org. Chem., 58, 3046 (1993).
11. 4 concentrated under reduced pressure, and purified by flash chromatography (silica gel, 20% EtOAc in hexane) to afford 96.2 mg (100%) of pure 2a.
12. M. Pereyre, J.-P. Quintard, and A. Rahm, Tin in Organic-Synthesis, Butterworth & Co. Ltd (1987).
13. 2(t-Bu)SnH, see: E. Nakamura, K. Sato, and Y. Imanishi, Synlett, 1995, 525.