Organic Letters 2009-04-02

Single-flask synthesis of N-acylated indoles by catalytic dehydrogenative coupling with primary alcohols.

Brooks E Maki, Karl A Scheidt

Index: Org. Lett. 11(7) , 1651-4, (2009)

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Abstract

Indoles and alcohols can be coupled in a dehydrogenative process catalyzed by tetrapropylammonium perruthenate. This efficient approach to indolylamides proceeds in a single flask under mild conditions. By employing substituted indoles and alkyl, branched, or benzylic alcohols, a variety of indolylamides can be formed. Aryl indolylamides can be functionalized through an additional dehydrogenative coupling to furnish elaborated polycyclic heterocycles similar to biologically active structures previously reported.