Mechanochemical Synthesis of Corannulene Flanked N-heterocyclic Carbene (NHC) Precursors and Preparation of Their Metal Complexes.

The synthesis of new compounds is an important pillar for the advancement of the field of chemistry and adjacent fields. In this regard, over the last decades huge efforts have been made to not only develop new molecular entities but also more efficient sustainable synthetic methodologies due to the increasing concerns over environmental sustainability. In this context, we have developed synthetic routes to novel corannulene flanked imidazolium bromide NHC precursors both in the solid-state and solution phases. Our work presents a comprehensive comparative study of mechanochemical routes and conventional solution-based methods. Green metrics and energy consumption comparison were performed for both routes revealing ball-milling generation of these compounds to be an environmentally greener technique to produce such precursors compared to conventional solvent-based methods. In addition, we have demonstrated proof-of-concept of the herein reported corannulene flanked NHCs to be robust ligands for transition metals and their ligand substitution reactions.