Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles

Rsuini U. Gutiérrez, Mayra Hernández-Montes, Aarón Mendieta-Moctezuma, Francisco Delgado, Joaquín Tamariz

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Abstract

An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.

Original languageEnglish
Article number4092
JournalMolecules
Volume26
Issue number13
DOIs
StatePublished - 1 Jul 2021

Keywords

  • Imines
  • Mercury(I)-catalyzed alkyne hydroamination
  • One-pot indole synthesis
  • Pd-catalyzed oxidative cyclization

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