gem-Heteroatom-Substituted Fluoroalkenes as Mimics of Amide Derivatives or Phosphates: A Comprehensive Review |
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Authors: | Solène Morand Prof Philippe Jubault Prof Jean-Philippe Bouillon Dr Samuel Couve-Bonnaire |
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Institution: | Normandie Université INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France |
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Abstract: | gem-Heteroatom-substituted fluoroalkenes have received little attention despite their great potential in medicinal chemistry or in fine chemistry. Indeed, due to the electronic and steric similarity between the fluoroalkene moiety and the amide bond as well as the high strength of the carbon-fluorine bond, these gem-heteroatom-substituted fluoroalkenes could be envisioned as stable mimics of various important organic functions, such as phosphates, carbamates, S-thiocarbamates and ureas. We present herein an overview describing the syntheses over the last decade of heteroatom-substituted fluoroalkenes in geminal position. This review will be divided into several sections covering each the common following heteroatom: oxygen-, nitrogen-, sulfur-, phosphorus-, boron- and silicon-substituted fluoroalkenes. |
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Keywords: | alkene amide fluorine isostere phosphate |
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