Frustrated Ion Pair-Enabled Cross-Electrophile Coupling of Unactivated Alkyl Electrophiles

Cross-electrophile coupling reactions have evolved into a major strategy for rapidly assembling important molecules, yet challenges remain for the formation of C(sp3)–C(sp3) bonds that form the core of nearly all organic compounds. Herein, we report a distinct, transition metal-free platform to form such bonds without the need for activating or stabilizing groups on the coupling partners. The reaction is enabled by an unusual single electron transfer in a frustrated ion pair and is complementary in terms of scope to transition metal-catalyzed processes. Moreover, we could further leverage this new mechanistic manifold in the design of other reactions, showing the broad potential of this new reactivity in organic synthesis.