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

LI Dixon, MA Carroll, TJ Gregson, GJ Ellames…

Index: Dixon, Luke I.; Carroll, Michael A.; Gregson, Thomas J.; Ellames, George J.; Harrington, Ross W.; Clegg, William Organic and Biomolecular Chemistry, 2013 , vol. 11, # 35 p. 5877 - 5884

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Citation Number: 10

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 ...