10.1002/cjoc.201100412
The research explores the Michael addition reactions of fluorinated nitro compounds with electron-deficient olefins to synthesize γ-fluoro-γ-nitro-esters, nitriles, and ketones that feature a fluorinated quaternary carbon center. The study aims to develop a practical method for constructing fluorinated nitro quaternary carbon centers, which are significant in pharmaceuticals and agrochemicals. The researchers used fluorinated nitro compounds as nucleophilic donors and electron-deficient olefins as acceptors, with N,N,N',N'-tetramethylguanidine (TMG) as the most effective catalyst. The reactions were optimized in dichloromethane (DCM) solvent, yielding the desired adducts in acceptable to good yields. The study concludes that this method provides a practical and efficient route for preparing biologically useful fluorinated derivatives, avoiding tedious decarboxylation steps and demonstrating potential applications in the synthesis of fluorinated pharmaceuticals and agrochemicals.