"Back-to-Front" Indole Synthesis using Silver(I) Catalysis: Unexpected C-3 Pyrrole Activation Mode Supported by DFT

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An efficient silver(I)-catalyzed method is reported for the synthesis of substituted indoles, most notably 5-hydroxy-derivatives, via π-acidic alkyne activation. Most methods for the preparation of indoles involve annulation of a benzene precursor, but the method reported herein is unusual in that pyrrole precursors are used. Density Functional Theory (DFT) studies suggest that these reactions proceed via initial activation of the pyrrole C-3 position before undergoing subsequent rearrangement, contradicting the conventional wisdom that pyrroles are more nucleophilic through C-2.

Original languageEnglish
Pages (from-to)6844-6850
Number of pages7
JournalACS Catalysis
Issue number8
Publication statusPublished - 3 Aug 2018

Bibliographical note

© 2018 American Chemical Society.


  • alkynes
  • cyclization
  • indoles
  • silver(I)
  • spirocycles

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