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Issue 24, 2014
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Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group

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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

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Publication details

The article was received on 13 Mar 2014, accepted on 06 May 2014, published on 06 May 2014 and first published online on 06 May 2014


Article type: Paper
DOI: 10.1039/C4OB00556B
Citation: Org. Biomol. Chem., 2014,12, 4156-4162
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    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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