These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
2 files

Differentiation and Functionalization of Adjacent, Remote C–H Bonds

submitted on 21.05.2019, 00:06 and posted on 21.05.2019, 15:26 by Hang Shi, Lu Yi, Jiang Weng, Katherine Bay, Xiangyang Chen, Keita Tanaka, pritha verma, Kendall N. Houk, jin-quan yu

Site-selective functionalizations of C–H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures1-4. Towards this goal, developing strategies to activate C–H bonds that are distal from a functional group is essential4-6. 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-leukemia agent, and hydrocinnamic acid substrates.


National Institute of General Medical Sciences grant 5R01GM102265


Email Address of Submitting Author


Scripps Research



ORCID For Submitting Author


Declaration of Conflict of Interest

no conflict of interest