Published In

Beilstein Journal of Organic Chemistry

Document Type

Article

Publication Date

5-2018

Subjects

Imides -- Arylation, Diaryliodonium, Hypercoordinate iodine, Metal-free, C–N coupling

Abstract

Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP)iodonium tosylate salts. The aryl transfer from the iodonium moiety occurs under electronic control with the electronrich trimethoxyphenyl group acting as a competent dummy ligand. The yields of N-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups.

Description

This article is part of the Thematic Series "Hypervalent iodine chemistry in organic synthesis".

Originally appeared in the Beilstein Journal of Organic Chemistry, volume 14, number 1, 2018. The definitive version of this article is the electronic one which can be found at: https://doi.org/10.3762/bjoc.14.90

© 2018 Basu et al.; licensee Beilstein-Institut.

This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

DOI

10.3762/bjoc.14.90

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