Issue 24, 2014

Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group

Abstract

The majority of alkynyl(aryl)iodonium salts reported in the literature are derived from iodobenzene. This article describes the effects of varying this iodoarene building block on the synthesis, reactivity and stability of these salts. Two procedures to synthesize a variety of known and novel alkynyl(aryl)iodonium tosylates directly from the iodoarene are reported. In the reactions of these salts, those derived from 2-iodoanisole gave superior results than the others tested in every reaction. Isothermal microcalorimetry indicated that these novel salts were significantly more stable and less prone to decomposition than all of the other derivatives.

Graphical abstract: Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group

Supplementary files

Article information

Article type
Paper
Submitted
13 Mar 2014
Accepted
06 May 2014
First published
06 May 2014
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2014,12, 4156-4162

Author version available

Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group

D. J. Hamnett and W. J. Moran, Org. Biomol. Chem., 2014, 12, 4156 DOI: 10.1039/C4OB00556B

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