Metal-free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution

Authors

Alexander H. Sandtorv, Portland State University
David R. Stuart, Portland State UniversityFollow

Published In

Angewandte Chemie International Edition

Document Type

Citation

Publication Date

12-1-2016

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.

Locate the Document

http://dx.doi.org/10.1002/anie.201610086

DOI

10.1002/anie.201610086

Persistent Identifier

http://archives.pdx.edu/ds/psu/19401

Citation Details

Sandtorv, A. H., & Stuart, D. R. (2016). Metal‐free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution. Angewandte Chemie, 128(51), 16044-16047.