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A selective,tin-free radical mediated synthesis of indoles based on a sulfonate template
Authors:Vincent James Gray  Jonathan D Wilden
Institution:Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK
Abstract:A synthesis of indoles based on a vinyl sulfonate template is described. The approach employs a sulfonate group which plays three discrete roles in the synthetic sequence. Firstly the highly electron-withdrawing sulfonate group behaves as an activating group for a 1,4-addition of an aniline to the unsaturated system. Secondly, the electron-withdrawing nature of the same group also allows it to behave as a radical stabilising group which facilitates radical cyclisation to an aromatic ring to yield a transient indoline. Finally, the pendant sulfonate group behaves as a leaving group to yield the indole.
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