Stereoconvergent Synthesis of Monofluoroalkenes via Photoinduced Dual Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with Redox-Active Esters

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 effic...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-04, Vol.87 (7), p.4654-4669
Main Authors: Lu, Xiao-Yu, Gao, Ang, Ge, Meng-Yuan, Xia, Ze-Jie, Liu, Qi-Le, Tao, Ting-Hua, Sun, Xiao-Mei
Format: Article
Language:English
Subjects:
Carboxylic Acids - chemistry
Decarboxylation
Esters - chemistry
Oxidation-Reduction
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c03088