Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles

Cedric Holzapfel, Etelinda Dasilva, Laetitia Den Drijver, Tyler Bredenkamp

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 %) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises RhI(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 % for the desired 3-substituted indoles.

Original languageEnglish
Pages (from-to)2912-2915
Number of pages4
JournalChemCatChem
Volume8
Issue number18
DOIs
Publication statusPublished - 21 Sept 2016

Keywords

  • alkynes
  • hydroformylation
  • regioselectivity
  • rhodium
  • synthesis design

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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