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Arylation of anilines: formation of diarylamines using diaryliodonium salts

Lookup NU author(s): Dr Michael Carroll, Reice Wood

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Abstract

Extensive studies on the reaction of the fluoride ion with diaryliodonium salts demonstrated that this is a generic process for the formation of fluoroarenes and has particular advantages for the preparation of fluorine-18 radiopharmaceuticals. During these studies it became apparent that nucleophiles other than the fluoride ion may be employed for generating substituted aromatics. This approach can be applied, using substituted anilines as the nucleophilic reagent, to the formation of a range of diarylamines in good yield. Optimised conditions for the reaction of a diaryliodonium salt with an aniline utilise TFA as the preferred counter-ion in DMF (130 °C, 24 h). © 2007 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Carroll MA, Wood RA

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2007

Volume: 63

Issue: 46

Pages: 11349-11354

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/j.tet.2007.08.076

DOI: 10.1016/j.tet.2007.08.076

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