α-halocarbonyl and benzyl halides and broadens the scope of
indium-mediated reductions.
References
1 P. Cintas, Synlett, 1995, 1087.
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Experimental
α-Halocarbonyl compounds have been prepared by standard
procedures.7 Indium metal was purchased from SRL, India,
and was used without any treatment.
General procedure for reduction
3 S. Araki, A. Imai, K. Shimizu, M. Yamada, A. Mori and
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Sim, Tetrahedron Lett., 1997, 38, 865; S. Araki, H. Nakano,
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6 C.-J. Li and T.-H. Chan, Organic Reactions in Aqueous Media, John
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A mixture of α-halocarbonyl compound or benzyl halide
(1 mmol) and indium metal (1 mmol, cut into small pieces)
in water (2 cm3) was sonicated in an ultrasonic cleaner for
a certain period of time as required to complete the reaction
(monitored by TLC). The reaction mixture was extracted with
ether and the ether extract was washed with brine and dried
(Na2SO4). Evaporation of solvent followed by purification by
silica gel column chromatography produced the corresponding
dehalogenated compound. Identification of the products was
made on the basis of IR and 1H NMR evidence in comparison
with authentic samples.
7 S. Motohashi and M. Satomi, Synthesis, 1982, 1021; P. Dowd and
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Acknowledgements
We gratefully acknowledge the financial support from CSIR,
New Delhi [Grant No. 01(1504)/98] for this investigation. P. D.
also thanks CSIR for his fellowship.
Communication 9/01493D
1140
J. Chem. Soc., Perkin Trans. 1, 1999, 1139–1140