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

ABSTRACT: 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.

SUBMITTER: Shi H

PROVIDER: S-EPMC7155936 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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

Shi Hang H Lu Yi Y Weng Jiang J Bay Katherine L KL Chen Xiangyang X Tanaka Keita K Verma Pritha P Houk Kendall N KN Yu Jin-Quan JQ

Nature chemistry 20200302 4

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 ...[more]

PMID: 32123338

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