title: Metal-free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution.
abstract: 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.
authors.affiliation: Department of Chemistry, Portland State University, Portland, OR, 97201, USA.
authors.forename: Alexander H
authors.initials: AH
authors.lastname: Sandtorv
authors.affiliation: Department of Chemistry, Portland State University, Portland, OR, 97201, USA.
authors.forename: David R
authors.initials: DR
authors.lastname: Stuart
keywords: alicyclic amines; amination; hypervalent iodine reagents; metal-free synthesis; nucleophilic aromatic substitution