Stereoconvergent Synthesis of Monofluoroalkenes via Photoinduced Dual Decarboxylative Cross-Coupling of α-Fluoroacrylic Acids with Redox-Active Esters.
Xiao-Yu LuAng GaoMeng-Yuan GeZe-Jie XiaQi-Le LiuTing-Hua TaoXiao-Mei SunPublished in: The Journal of organic chemistry (2022)
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(sp 2 )-C(sp 3 ) 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.