Stereoconvergent Synthesis of Monofluoroalkenes viaPhotoinduced Dual Decarboxylative Cross-Coupling ofα-Fluoroacrylic Acids with Redox-Active Esters

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

Automated summary

A new strategy for synthesizing monofluoroalkenes using α-fluoroacrylic acids and N-hydroxyphthalimide (NHPI) redox-active esters as coupling partners is developed. This decarboxylative reaction enables the formation of C(sp2)-C(sp3) bonds, providing a practical and efficient approach for constructing various monofluoroalkenes with excellent functional group compatibility and Z-stereoselectivity. Furthermore, this work also serves as a platform for modifying complex biologically active molecules containing carboxylic acids.