Synthesis of α‐Fluoroenones by Elimination of α‐Chloro‐α‐fluoroketones

A new synthetic route to α‐fluoroenones was developed. Decarboxylative chlorination of α‐fluoro‐β‐oxocarboxylic acids afforded α‐chloro‐α‐fluoroketones, and subsequent base‐mediated elimination yielded the corresponding α‐fluoroenones. The method successfully produced both cyclic and acyclic α‐fluor...

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Veröffentlicht in:Asian journal of organic chemistry 2019-05, Vol.8 (5), p.691-693
Hauptverfasser: Naruse, Atsushi, Kitahara, Kazumasa, Iwasa, Seiji, Shibatomi, Kazutaka
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Sprache:eng
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Zusammenfassung:A new synthetic route to α‐fluoroenones was developed. Decarboxylative chlorination of α‐fluoro‐β‐oxocarboxylic acids afforded α‐chloro‐α‐fluoroketones, and subsequent base‐mediated elimination yielded the corresponding α‐fluoroenones. The method successfully produced both cyclic and acyclic α‐fluoroenones in good yields. Furthermore, the method was applicable to the synthesis of not only aromatic but also aliphatic enones. The method allows the preparation of a variety of α‐fluoroenones, which are useful intermediates for the synthesis of various fluoroorganic compounds. A new synthetic route to α‐fluoroenones has been developed. Decarboxylative chlorination of α‐fluoro‐β‐oxocarboxylic acids afforded α‐chloro‐α‐fluoroketones, and subsequent base‐mediated elimination yielded the corresponding α‐fluoroenones in good yield. The method could be applied to the synthesis of a variety of α‐fluoroenones, including both cyclic and acyclic enones.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900072