Friedel-Crafts Addition of 3-Alkylated Indoles to Aldehydes: 2-Hydroxyalkylation Promoted by Trimethylsilyl Trifluoromethanesulfonate
Abstract
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,6-lutidine, 3-alkylated indoles undergo Friedel-Crafts silyloxyalkylation when treated with nonenolizable aldehydes. The reaction is general across a wide range of aromatic aldehydes and tolerates a variety of N-alkylated indoles. Deprotection of the silylated product occurs under standard conditions, and in certain cases the initial TMS-protected product can be isolated in high yield.
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