Our group has recently reported a series of ruthenium-based metathesis catalysts that contain a chelating NHC. These catalysts demonstrate high Z-selectivity in a variety of metathesis reactions including cross metathesis, ring-closing metathesis and ring-opening metathesis polymerization.  However, the substrate scope has so far been limited to relatively unhindered olefins. In order to probe the origin of this selectivity, a series of catalysts with N-heterocyclic carbene (NHC) substituents of varying steric bulk were prepared.  These catalysts were subsequently examined for improved reactivity in a range of olefins that contain bulky substituents. In addition, the mechanism of the C-H-activation step in the synthesis of such catalysts was probed through variation of the sterics and electronics of both the adamantyl and aryl NHC substituents.

Design and synthesis of new ruthenium-based catalysts for improved activity in challenging Z-selective metathesis reactions

245th National Meeting (2013)

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