Dramatic Effect of Solvent Hydrogen Bond Basicity on the Regiochemistry of SNAr Reactions of Electron-Deficient Polyfluoroarenes
Organic Letters2009Vol. 11(24), pp. 5662–5664
Citations Over TimeTop 10% of 2009 papers
Abstract
It was found that solvent hydrogen bond basicity (SHBB) significantly affects the regiochemistry of the S(N)Ar reaction between secondary amines and activated polyfluoroarenes. A plausible mechanism involving a six-membered transition state is invoked for the formation of an ortho-substituted isomer, which is likely organized by a hydrogen bond. Evidence for this hypothesis is presented, and a regioselective amination reaction of activated polyfluoroarenes has been developed.
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