Towards Sustainable Catalysis – Highly Efficient Olefin Metathesis in Protic Media Using Phase Labelled Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Catalysts
Márton Nagyházi, Gábor Turczel, Áron Balla, Gábor Szálas, Imre Tóth, G. Tamás Gál, Bombicz Petra, Paul T. Anastas, Róbert Tuba
Abstract
Abstract New generations of Hoveyda and bis‐carbene type of ruthenium‐based olefin metathesis catalysts ( 10 and 12 ), containing cationic cyclic alkyl amino carbene (CAAC) ligands, have been synthetized. The catalysts show exceptional stability and activity in environmentally benign, protic media. Various olefin metatheses reactions of OH functionalized feedstock (e. g. RCM, ROMP CM) can be carried out at as low as 0.05 mol % catalyst loading in methanol, isopropanol, water or methanol/water solvent mixture, accomplishing the lowest applied catalyst loading reported so far in these media. The facile olefin metathesis of renewable feedstocks including phospholipids ( 23 ) and vegetable oils ( 20 ) in protic media has also been demonstrated.