A selective, tin-free radical mediated synthesis of indoles based on a sulfonate template

作者：Gray Vincent James; Wilden Jonathan D^*

来源：Tetrahedron Letters, 2012, 53(1): 41-44.

DOI：10.1016/j.tetlet.2011.10.093

• Sulfonate ester
• Indole
• Radical
• Cyclisation

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.

• 出版日期2012-1-4