1352621-99-8Relevant articles and documents
A selective, tin-free radical mediated synthesis of indoles based on a sulfonate template
Gray, Vincent James,Wilden, Jonathan D.
, p. 41 - 44 (2012/01/05)
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.