Reactivity and Selectivity of Azaspirocycles in Radical C–H Functionalization

Investigations of saturated spirocycles
toward selective C–H
functionalization reactions are scarce, despite their potential applications.
In this work, we uncovered fundamental reactivity and selectivity
differences between saturated heterocycles and their spirocyclic analogues
using a model radical C–H xanthylation coupled with computational
analysis. Ultimately, this study sheds light on the fundamental, understudied
radical reactivity of spirocycles, thereby allowing for a pronounced
chemical tunability that will prove to be advantageous in the expansion
of their chemical space and applications in medicinal chemistry.