Magnesium iodide promoted defluorinative reactions of 2,2-difluorocyclopropyl aryl ketones with aryl imines: A new, general synthesis of 2-alkylideneazetidines

Upon treatment with anhydrous MgI2, 2,2-difluorocyclopropyl aryl ketones undergo a ring-opening process leading to complete loss of fluorine. When carried out in the presence of aryl imines, the reaction leads to a novel synthesis of 2-alkylideneazetidenes. A fluorine-free allenyl ketone is proposed as an intermediate in these reactions.

Graphical abstractA novel synthesis of 2-alkylideneazetidenes via the defluorinative ring-opening reaction of 2,2-difluorocyclopropyl ketones with imines.Figure optionsDownload full-size imageDownload as PowerPoint slide