Schiff-base substituted ruthenium carbon complexes were prepared by treating Grubbs' catalyst with Schiff-base ligand salts that potentially supports chiral substituents.  These complexes demonstrated high metathesis activity in organic solvents. The complexes were prepared in three steps in moderate yields but the final step required the use of Schiff-base ligands in the form of their thallium salts (toxic!). Using microwave irradiation, our lab prepared the aforementioned organometallic complex in NMR tubes using sodium salts.  However, scale-up of the reaction proved to be difficult.  The goal of this study is to determine the best microwave method for producing gram quantities of Schiff-base substituted ruthenium complexes using nontoxic salts. Q-NMR analyses of the complexes' carbene peak were conducted to determine the best microwave method to effect a quantitative reaction. The methodology will provide a nontoxic route into ruthenium Schiff-base catalyst that possesses chiral character, which in turn, opens the possibility for asymmetric catalysts.

Preparing gram quantities of ruthenium bidentate Schiff-base complexes via microwave irradiation

243rd National Meeting (2012)

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