Metal-free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution
Angewandte Chemie International Edition
A mild and metal-free approach to C−N coupling is described that employs diaryliodonium salt electrophiles and secondary aliphatic amine nucleophiles. This reaction results in direct ipso-substitution of the iodonium moiety and unsymmetrical aryl(TMP)iodonium salts are primarily employed. Moreover, arene substituents and substitution patterns that currently pose a challenge to classical metal-free methods are accommodated and the alicyclic amine nucleophiles used here are unprecedented in other contemporary metal-free C−N coupling reactions.
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Sandtorv, A. H., & Stuart, D. R. (2016). Metal‐free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution. Angewandte Chemie, 128(51), 16044-16047.