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Synthesis of α‐Fluoroenones by Elimination of α‐Chloro‐α‐fluoroketones
Author(s) -
Naruse Atsushi,
Kitahara Kazumasa,
Iwasa Seiji,
Shibatomi Kazutaka
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900072
Subject(s) - chemistry , base (topology) , organic chemistry , combinatorial chemistry , reaction conditions , elimination reaction , catalysis , mathematical analysis , mathematics
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.