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

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.

SUBMITTER: Maki BE

PROVIDER: S-EPMC2782717 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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

Maki Brooks E BE Scheidt Karl A KA

Organic letters 20090401 7

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 pre ...[more]

PMID: 19320508

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