Simple generation of various α-monofluoroalkyl radicals by organic photoredox catalysis: modular synthesis of β-monofluoroketones
Ryo Taniguchi, Naoki Noto, Seiya Tanaka, Keigo Takahashi, Sujan K. Sarkar, Ryoko Oyama, Manabu Abe, Takashi Koike, Munetaka Akita
Abstract
A metal-free and operationally simple strategy for the generation of various α-monofluoroalkyl radicals has been developed. A combination of 1,4-bis(diarylamino)naphthalene photocatalyst and sulfoximine-based fluoroalkylating reagents is the key to success. The protocol can be applied to modular synthesis of β-monofluoroketones through radical monofluoroalkylation of alkenyl acetates.
Topics & Concepts
Photoredox catalysisRadicalCatalysisOrganic synthesisSimple (philosophy)ChemistryModular designCombinatorial chemistryPhotochemistryOrganic chemistryPhotocatalysisComputer scienceOperating systemEpistemologyPhilosophyFluorine in Organic ChemistryRadical Photochemical ReactionsInorganic Fluorides and Related Compounds