Nickel-Catalyzed C(sp3)-C(sp3) Cross-Electrophile Coupling of InSitu Generated NHP Esters with Unactivated Alkyl Bromides

The formation of C(sp3)-C(sp3) bonds by cross-coupling remains a challenge in synthesis. Here, we demonstrate atwo-step, one-pot protocol for the in situ generation ofN-hydroxyphthalimide esters and their nickel-catalyzed cross-electrophilecoupling with unactivated alkyl bromides for the construction of 1 degrees/1 degrees C(sp3)-C(sp3) bonds. The conditions tolerate an array of functionalgroups, and mechanistic studies indicate that both substrates areconverted to alkyl radicals during the reaction.

Automated summary

This study successfully develops a two-step, one-pot protocol for the in situ generation of N-hydroxyphthalimide esters and their nickel-catalyzed cross-electrophile coupling with unactivated alkyl bromides, enabling the construction of C(sp3)-C(sp3) bonds. The conditions tolerate various functional groups, and mechanistic studies demonstrate the conversion of both substrates to alkyl radicals during the reaction.