Differentiation and Functionalization of Adjacent, Remote C–H Bonds
2019
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.
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