Olefin metathesis has had a major impact on organic synthesis, and holds enormous potential in applications ranging from pharmaceutical manufacturing to the metathesis of renewable oils. A long-recognized challenge, however, is low metathesis productivity. The important ruthenium metathesis catalysts, although justly prized for their ease of handling, readily decompose via both intrinsic and induced pathways. Of keen interest, therefore, is the extraordinary productivity established for catalysts bearing a cyclic alkyl amino carbene (CAAC; Figure 1). Within the topical contexts of metathesis macrocyclization and ethenolysis of renewable oils, turnover numbers are up to 2 orders of magnitude higher than those attainable with leading H<sub>2</sub>IMes catalysts. The basis for this performance difference will be outlined, in studies focusing on the resistance to decomposition of key catalytic intermediates.

Origin of the breakthrough success of Ru-CAAC catalysts in olefin metathesis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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