Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides

M. Beller, C. Breindl, T. H. Riermeier, A. Tillack

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Abstract

Aliphatic and aromatic amines react with 2- and 3-chlorostyrene in the presence of potassium tert-butoxide to give N-substituted 2,3-dihydroindoles in good yields. The combination of this domino-amination protocol with a suitable dehydrogenation reaction gives access to pharmacologically interesting indoles in a one-pot procedure. Overall product yields of N-substituted indoles > 50% are obtained by this method starting from commercially available substrates. In addition to the intramolecular base-promoted amination of aromatic C-Cl, bonds, metal-free intermolecular aminations of aryl chlorides with primary and secondary amines are described. The use of potassium tert-butoxide as base allows the synthesis of various anilines in good to excellent yields. Due to the formation of aryne intermediates, either N-substituted anilines or meta-substituted anilines are produced with excellent selectivities.

Original languageEnglish
Pages (from-to)1403-1412
Number of pages10
JournalJournal of Organic Chemistry
Volume66
Issue number4
DOIs
StatePublished - 23 Feb 2001
Externally publishedYes

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