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Iron-Catalyzed para -Selective C-H Allylation of Aniline Derivatives.

Qiulin YouXin XiaoYang ShiYimin WuGuangying Tan
Published in: Organic letters (2023)
Transition-metal-catalyzed directed C-H allylation of arenes offers an efficient and straightforward approach to construct value-added allylic arenes. However, these reactions are often performed with precious transition-metal catalysts and mainly limited to ortho- C-H allylation of arenes. Herein, we disclose a novel iron-catalyzed para -C-H allylation of aniline derivatives with allyl alcohols via a chelation-induced strategy, providing various allylic arenes in good yields with excellent regio- and chemoselectivity. A simple FeCl 3 ·6H 2 O is employed as a catalyst, serving a dual role in the reaction: (1) coordination with N -arylpicolinamide to alter the electronic property of the aromatic ring and (2) reaction with allyl alcohol to form allyl-Fe species.
Keyphrases
  • transition metal
  • room temperature
  • ionic liquid
  • iron deficiency
  • metal organic framework
  • amino acid
  • reduced graphene oxide