Flow chemistry as enabling technology for controlling the reactivity of fluorocarbenoids

Fluorinated compounds have attracted a great deal of interest by scientists involved in many field of science and technology. However, despite their importance, the selective introduction of monofluoromethyl groups (-CH2F) into a small organic molecules is still a challenging task. Unlike the extensive use of other halocarbenoids in organic synthesis, fluorocarbenoids are still considered the "beast" in carbenoid chemistry due to their chemical instability that severely limited its use in synthetic process. In this communication, we report how we tried to face this challenge by employing flow microreactor technology. Fluorocarbenoids could be effectively generated and trapped with electrophiles providing a new successfully application of flash chemistry in short-lived intermediate reactions. Mechanistic insights and applications will be presented.