Stereospecific Synthesis of Tri- and Tetrasubstituted α‑Fluoroacrylates by Mizoroki−Heck Reaction
Résumé
Ligand-free, efficient, palladium-catalyzed Mizoroki–Heck reaction between methyl α-fluoroacrylate and arene or hetarene iodides is reported for the first time. The reaction is stereospecific and provides fair to quantitative yields of fluoroalkenes. The Mizoroki–Heck reaction starting from more hindered and usually reluctant trisubstituted acrylate, to access tetrasubstituted fluoroalkenes, is also reported. Finally, the use of a three-step synthesis sequence, including Mizoroki–Heck reaction, allows the synthesis of fluorinated analogues of therapeutic agents with high yield.