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Single step polyfluoroarylation of amides

Noel, Alyssa
Hamilton, Matthew
Jesperson, Daniel
Keen, Brockton
Per- and polyfluoroarenes are important synthetic chemistry targets because they are active components in many pharmaceuticals, agrichemicals, and industrial manufacturing products. Many of the current methods of synthesizing these fluoroarenes involves selectively adding fluorines one at a time. These procedures are rudimentary and often demand long and harsh reaction conditions and often result in poor yields. Novel substrates can be reached, however, through selective hydrodefluorination or functionalization, i.e. fluorine sculpting. This research compliments recently developed chemistry which synthesizes starting material fluoroarenes in two steps by shortening the synthesis by 50%. This chemistry utilizes nucleophilic aromatic substitution to synthesize per- and poly-fluoroaryl amides in a single step under mild reaction conditions which can then be utilized for fluorine sculpting.