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Issue 35, 2013
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Unprecedented regiochemical control in the formation of aryl[1,2-a]imidazopyridines from alkynyliodonium salts: mechanistic insights

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Abstract

Aryl(alkynyl)iodonium salts have been demonstrated to be valuable precursors to a diverse range of heteroaromatic ring systems including aryl[1,2-a]imidazopyridines. Successful application, using the recently described aryl(alkynyl)iodonium trifluoroacetate salts, is described, highlighting for the first time that the regioselectivity of this process is both counter-ion and concentration dependent. Studies with a carbon-13 labelled substrate established that the reactions of alkynyliodonium salts are highly complex and that multiple mechanistic processes appear to be underway simultaneously.

Graphical abstract: Unprecedented regiochemical control in the formation of aryl[1,2-a]imidazopyridines from alkynyliodonium salts: mechanistic insights

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Publication details

The article was received on 28 May 2013, accepted on 12 Jul 2013 and first published on 15 Jul 2013


Article type: Paper
DOI: 10.1039/C3OB41112E
Citation: Org. Biomol. Chem., 2013,11, 5877-5884
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    Unprecedented regiochemical control in the formation of aryl[1,2-a]imidazopyridines from alkynyliodonium salts: mechanistic insights

    L. I. Dixon, M. A. Carroll, T. J. Gregson, G. J. Ellames, R. W. Harrington and W. Clegg, Org. Biomol. Chem., 2013, 11, 5877
    DOI: 10.1039/C3OB41112E

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