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A radical based addition-elimination route for the preparation of indoles

Murphy, J.A. and Scott, K.A. and Sinclair, R.S. and Martin, C.G. and Kennedy, A.R. and Lewis, N. (2000) A radical based addition-elimination route for the preparation of indoles. Journal of the Chemical Society, Perkin Transactions 1, 2000 (15). pp. 2395-2408. ISSN 1472-7781

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Indoles, including tricyclic derivatives, are produced by cyclisations of aryl radicals onto vinyl halides followed by elimination of halide radical and tautomerism of the resulting product; the aryl radicals are produced using clean methodology either by reaction of iodide ions with arenediazonium salts or by reaction of phosphorus-centred radicals with aryl iodides.