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Differentiation and functionalization of remote C-H bonds in adjacent positions.

  • Author(s): Shi, Hang
  • Lu, Yi
  • Weng, Jiang
  • Bay, Katherine L
  • Chen, Xiangyang
  • Tanaka, Keita
  • Verma, Pritha
  • Houk, Kendall N
  • Yu, Jin-Quan
  • et al.

Site-selective functionalization of C-H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures. Towards this goal, it is essential to develop strategies to activate C-H bonds that are distal from a functional group. In this context, distinguishing remote C-H bonds on adjacent carbon atoms is an extraordinary challenge due to the lack of electronic or steric bias between the two positions. Herein, we report the design of a catalytic system leveraging a remote directing template and a transient norbornene mediator to selectively activate a previously inaccessible remote C-H bond that is one bond further away. The generality of this approach has been demonstrated with a range of heterocycles, including a complex anti-leukaemia agent and hydrocinnamic acid substrates.

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