Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives

A method for amide-directed Ni-catalyzed diaster-eoselective arylboration of cyclopentenes is disclosed. The reaction allows for the synthesis of sterically congested cyclopentane scaffolds that contain an easily derivatized boronic ester and amide functional handles. The nature of the amide directing group and its influence on the reaction outcome are investigated and ultimately reflect a predictably selective reaction based on the solvent and base counterion.

Automated summary

The method utilizes amide-directed nickel catalysis to achieve highly selective synthesis of cyclopentane scaffolds containing boronic ester and amide functional groups. The nature of the amide directing group influences the reaction outcome, leading to predictably selective reactions based on the solvent and base counterion.