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Synthesis and Reactivity of Aryl(alkynyl)iodonium Salts

Lookup NU author(s): Dr Michael Carroll, Dr Ross Harrington, Emeritus Professor Bill CleggORCiD

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Abstract

The first practical, yet simple, preparation of aryl(alkynyl)iodonium trifluoroacetate salts is described. The generic nature of this synthetic method has allowed the production of a range of aryl(alkynyl)iodonium trifluoroacetate salts with independent variation of both the alkynyl and aryliodo groups in yields of 30–85 %. Application of these new reagents to the synthesis of a series of 2-arylfuro[3,2-c]pyridines (40–64 %) highlights the potential of this class of materials as precursors to bioactive heterocyclic structures. These experiments have also demonstrated that, in this case, the effect of the aryliodo group on the reaction is negligible.

Publication metadata

Author(s): Dixon LI, Carroll MA, Gregson TJ, Ellames GJ, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: European Journal of Organic Chemistry

Year: 2013

Volume: 2013

Issue: 12

Pages: 2334-2345

Print publication date: 08/03/2013

ISSN (print): 1434-193X

ISSN (electronic): 1099-0690

Publisher: Wiley

URL: http://dx.doi.org/10.1002/ejoc.201300092

DOI: 10.1002/ejoc.201300092

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