Oxidative coupling of indoles using thallium(III) trifluoroacetate

P. A. Keller, University of Wollongong
N. R. Yepuri, University of Wollongong
M. J. Kelso, University of Wollongong
M. Mariani, University of Wollongong
B. W. Skelton, University of Western Australia
A. H. White, University of Western Australia

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This article was originally published as Keller, PA, Yepuri, NR, Kelso, MJ, Mariani, M, Skelton, BW & White, AH, Oxidative coupling of indoles using thallium(III) trifluoroacetate, Tetrahedron, 64(33), 2008, 7787-7795. Original journal article available here

Abstract

The oxidative coupling of polysubstituted electron-rich indoles mediated by thallium trifluoroacetate was found to be a facile, clean, and high yielding reaction. Indolic coupling sites were determined by the nature of the substituents present, with dimerisation at the indole 2-position being the dominant outcome. Indoles bearing two potential reaction sites with similar reactivity were additionally found to undergo heterocoupling.