Synthesis of a C1-symmetric Box macrocycle and studies towards active-template synthesis of mechanically planar chiral rotaxanes

A C1-symmetric Box macrocycle has been synthesized for the first time. The Box macrocycle along with other C1 and C2-symmetric Box ligands were evaluated and compared as ligands in the Cadiot–Chodkiewicz, oxidative Heck and CuAAC ‘click’ reactions as part of our studies towards achieving active-metal template synthesis of mechanically planar chiral rotaxanes. This study constitutes the first report of Cadiot–Chodkiewicz and CuAAC ‘click’ reactions using Box ligands, as well as the first dedicated study of oxidative Heck reactions using Box ligands.