Volume 2013, Issue 12 p. 2334-2345
Full Paper

Synthesis and Reactivity of Aryl(alkynyl)iodonium Salts

Luke I. Dixon

Luke I. Dixon

School of Chemistry, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK, Fax: +44-(0)191-2226929

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Michael A. Carroll

Michael A. Carroll

School of Chemistry, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK, Fax: +44-(0)191-2226929

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Thomas J. Gregson

Thomas J. Gregson

Department of Isotope Chemistry and Metabolite Synthesis, Sanofi-aventis, Willowburn Avenue, Alnwick, Northumberland, NE66 2JH, UK

Current address: Department of Isotope Chemistry, Covance Laboratories, Alnwick, Northumberland, NE66 2JH, UK

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George J. Ellames

George J. Ellames

Department of Isotope Chemistry and Metabolite Synthesis, Sanofi-aventis, Willowburn Avenue, Alnwick, Northumberland, NE66 2JH, UK

Current address: Department of Isotope Chemistry, Covance Laboratories, Alnwick, Northumberland, NE66 2JH, UK

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Ross W. Harrington

Ross W. Harrington

School of Chemistry, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK, Fax: +44-(0)191-2226929

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William Clegg

William Clegg

School of Chemistry, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK, Fax: +44-(0)191-2226929

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First published: 08 March 2013
Citations: 32

Graphical 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 these materials with independent variation of both alkynyl and aryliodo groups. Application to the synthesis of a series of 2-arylfuro[3,2-c]pyridines is also demonstrated.

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.