Merger of visible-light photoredox catalysis and C–H activation for the room-temperature C-2 acylation of indoles in batch and flow

Upendra Sharma, H.P.L. Gemoets, F.S. Schroeder, T. Noël, E.V. van der Eycken

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Abstract

A mild and versatile protocol for the C-H acylation of indoles via dual photoredox/transition-metal catalysis was established in batch and flow. The C-H bond functionalization occurred selectively at the C-2 position of N-pyrimidylindoles. This room-temperature protocol tolerated a wide range of functional groups and allowed for the synthesis of a diverse set of acylated indoles. Various aromatic as well as aliphatic aldehydes (both primary and secondary) reacted successfully. Interestingly, significant acceleration (20 to 2 h) and higher yields were obtained under micro flow conditions.

Original languageEnglish
Pages (from-to)3818-3823
Number of pages6
JournalACS Catalysis
Volume7
Issue number6
DOIs
Publication statusPublished - Jun 2017

Keywords

  • C-H acylation
  • dual catalysis
  • flow chemistry
  • indoles
  • palladium catalysis
  • photocatalysis

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