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Selective and Scalable Perfluoroarylation of Nitroalkanes

Day, Jon I., Weaver, Jimmie D.
Journal of organic chemistry 2017 v.82 no.13 pp. 6801-6810
Lewis bases, aromatic hydrocarbons, carbon, chemical reactions, chemical structure, chromatography, halogens, nitroalkanes, organic chemistry, regioselectivity
Functionalized per- and polyfluoroarenes are important building blocks, with many industrially and medicinally important molecules containing them. Nucleophilic aromatic substitution can be employed as a quick and straightforward way to synthesize these building blocks. While many methods to derivatize fluoroarenes exist that use heteroatom centered nucleophiles, there are fewer methods that use carbon centered nucleophiles, and of those many are poorly defined. This work presents the SNAr reaction of nucleophiles generated from nitroalkanes with a variety of fluorinated arenes. Given that the products are versatile, accessing polyfluorinated arene building blocks in substantial scale is important. This method is highly regioselective, and produces good to moderate yields on a large scale, sans chromatography, and thus fulfills this need. In addition, the regioselectivity of the addition was probed using both DFT calculations and experimentally via halogen exchange.