2-And 3-phenylsulfonylindoles-synthetic equivalents of unsubstituted indole in n-alkylation reactions

Abstract

The N-alkylation of 2- and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions. © 2010 Springer Science+Business Media, Inc.