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J Org Chem ; 87(7): 4654-4669, 2022 04 01.
Article in English | MEDLINE | ID: mdl-35313107

ABSTRACT

Herein, a new strategy for the synthesis of monofluoroalkenes via employing α-fluoroacrylic acids and N-hydroxyphthalimide (NHPI) redox-active esters as coupling partners has been developed. This decarboxylative reaction enabled the formation of C(sp2)-C(sp3) bonds to provide a practical and efficient approach for the construction of a variety of monofluoroalkenes, which are key structural motifs in organic chemistry, under mild reaction conditions. The protocol exhibited excellent functional group compatibility and delivered monofluoroalkene products with excellent Z-stereoselectivity. This work also provides a platform for the modification of complex biologically active molecules containing carboxylic acids.


Subject(s)
Carboxylic Acids , Esters , Carboxylic Acids/chemistry , Decarboxylation , Esters/chemistry , Oxidation-Reduction
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