Categories: C-H Bond Formation >
Reduction of carboxyl compounds to aldehydes
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Recent Literature
A palladium-catalyzed reduction of 2-pyridinyl esters using hydrosilanes is
applicable to the preparation of aliphatic, aromatic, and α,β-unsaturated
aldehydes. Various functional groups, such as fluoro, methoxy, aldehyde, acetal,
and ester, are tolerated.
J. Nakanishi, H. Tatamidani, Y. Fukumoto, N. Chatani, Synlett,
2006, 869-872.
Treatment of ethanethiol esters with triethylsilane and palladium on carbon
at ambient temperature furnished aldehydes. In addition, a variety of
ketones has been prepared by a palladium-catalyzed reaction of ethanethiol
esters with organozinc reagents. Both transformations tolerate various
functional groups, including esters, ketones, aromatic halides and
aldehydes.
H. Tokuyama, S. Yokoshima, T. Yamashita, S.-C. Lin, L. Li, T. Fukuyama,
J. Braz. Chem. Soc., 1998, 9, 381-387.
Reduction of ethanethiol esters of α-amino acids to α-amino aldehydes by
triethylsilane and catalytic palladium-on-carbon is described. α-Amino
aldehydes with Boc, Cbz, or Fmoc protection could be obtained without
racemization in high yield.
H. Tokuyama, S. Yokoshima, S.-C. Lin, L. Li, T. Fukuyama, Synthesis,
2002, 1121-1123.
