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Ruthenium-Catalyzed para-Selective C-H Alkylation of Aniline Derivatives.

Jamie A LeitchClaire L McMullinAndrew J PatersonMary F MahonYunas BhonoahChristopher G Frost
Published in: Angewandte Chemie (International ed. in English) (2017)
The para-selective C-H alkylation of aniline derivatives furnished with a pyrimidine auxiliary is herein reported. This reaction is proposed to take place via an N-H-activated cyclometalate formed in situ. Experimental and DFT mechanistic studies elucidate a dual role of the ruthenium catalyst. Here the ruthenium catalyst can undergo cyclometalation by N-H metalation (as opposed to C-H metalation in meta-selective processes) and form a redox active ruthenium species, to enable site-selective radical addition at the para position.
Keyphrases
  • room temperature
  • ionic liquid
  • highly efficient
  • metal organic framework
  • molecular docking
  • density functional theory