Merger of Visible-Light Photoredox Catalysis and C-H Activation for the Room-Temperature C-2 Acylation of Indoles in Batch and Flow

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. © 2017 American Chemical Society.

Authors
Sharma U.K.1 , Gemoets H.P.L.3 , Schröder F.1 , Noël T.3 , Van Der Eycken E.V.
Journal
Publisher
American Chemical Society
Number of issue
6
Language
English
Pages
3818-3823
Status
Published
Volume
7
Year
2017
Organizations
  • 1 Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 2 Peoples' Friendship University of Russia, RUDN University, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
  • 3 Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Process Technology, Eindhoven University of Technology, Den Dolech 2, Eindhoven, 5612 AZ, Netherlands
Keywords
C-H acylation; dual catalysis; flow chemistry; indoles; palladium catalysis; photocatalysis
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/5478/