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Facile Palladium-Mediated Conversion of Ethanethiol Esters to Aldehydes and Ketones

Hidetoshi Tokuyama, Satoshi Yokoshima, Tohru Yamashita, Shao-Cheng Lin, Leping Li and Tohru Fukuyama*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: fukuyamamol.f.u-tokyo.ac.jp

H. Tokuyama, S. Yokoshima, T. Yamashita, S.-C. Lin, L. Li, T. Fukuyama, J. Braz. Chem. Soc., 1998, 9, 381-387.

DOI: 10.1590/S0103-50531998000400011



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Abstract

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.

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Details

The article discusses a palladium-mediated method for converting ethanethiol esters into aldehydes and ketones. The process involves treating ethanethiol esters with triethylsilane and palladium on carbon at room temperature to produce aldehydes. Additionally, ketones are synthesized by reacting ethanethiol esters with organozinc reagents in the presence of a palladium catalyst. This method is notable for its mild conditions and high chemoselectivity, tolerating various functional groups such as esters, ketones, aromatic halides, and aldehydes. The procedure is particularly effective for synthesizing α-amino aldehyde and α-amino ketone derivatives from L-α-amino thiol esters without causing racemization. The article also details the preparation of ethanethiol esters from carboxylic acids using a mixed anhydride method and demonstrates the utility of the method in synthesizing complex natural products. The findings offer a powerful alternative for transforming acids into aldehydes and ketones, potentially benefiting synthetic organic chemistry.


Reduction of Ethanethiol Esters to Aldehydes

H. Tokuyama, S. Yokoshima, S.-C. Lin, L. Li, T. Fukuyama, Synthesis, 2002, 1121-1123.


Key Words

thioesters, aldehydes, ketones, triethylsilane, organozinc reagents, palladium catalysts, Fukuyama Coupling, Fukuyama Reduction


ID: JXX-Y1998-180