Article ID Journal Published Year Pages File Type
1315436 Journal of Fluorine Chemistry 2008 13 Pages PDF
Abstract

In an effort to find new methodologies to introduce difluoromethylene and trifluoromethyl moieties into organic molecules of synthetic and biological interest, tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of a series of good electron-acceptors such as bromodifluoromethyl heterocycles, chlorodifluoromethylated ketones as well as perfluoroalkyl iodides; the corresponding anions thus generated under very mild conditions, were successfully engaged in a number of intra- and intermolecular coupling reactions with a series of electrophiles (aldehydes, ketones, α-keto esters, N-tosyl aldimines, acyl chlorides, diol sulphates, disulfides, and diselenides). The corresponding adducts were usually obtained in moderate to good yields and the present method was found to be as good or even better as other most popular approaches. This paper gives an overview of our research efforts in this area as well as results from other groups.

Graphical abstractIn an effort to find new methodologies to introduce difluoromethylene and trifluoromethyl moieties into organic molecules of synthetic and biological interest, the tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of a series of good electron-acceptors such as bromodifluoromethyl heterocycles, chlorodifluoromethylated ketones as well as perfluoroalkyl iodides; the corresponding anions thus generated under very mild conditions, were successfully engaged in a number of intra- and intermolecular coupling reactions with a series of electrophiles (aldehydes, ketones, α-keto esters, N-tosyl aldimines, acyl chlorides, diol sulphates, disulfides, and diselenides). The corresponding adducts were usually obtained in moderate to good yields and the present method was found to be as good or even better as other most popular approaches. This paper gives an overview of our research efforts in this area as well as results from other groups. Figure optionsDownload full-size imageDownload as PowerPoint slide

Related Topics
Physical Sciences and Engineering Chemistry Inorganic Chemistry
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