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Differentiation and Functionalization of Adjacent, Remote C–H Bonds

preprint
submitted on 21.05.2019 and posted on 21.05.2019 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.

Funding

National Institute of General Medical Sciences grant 5R01GM102265

History

Email Address of Submitting Author

yu200@scripps.edu

Institution

Scripps Research

Country

USA

ORCID For Submitting Author

0000-0003-3560-5774

Declaration of Conflict of Interest

no conflict of interest

Exports