ArticleJournal of the American Chemical Society2019
Catalyst Behavior in Metal-Catalyzed Carbonyl-Olefin Metathesis.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Article
- Controlling Catalyst Behavior in Lewis Acid-Catalyzed Carbonyl-Olefin Metathesis.Journal of the American Chemical Society · 2023Article
- Synthesis and characterization of trigonal bipyramidal FePolyhedron · 2021Article
- Carbonyl-Olefin Metathesis.Chemical reviews · 2021Review
- Combined Theoretical and Experimental Investigation of Lewis Acid-Carbonyl Interactions for Metathesis.ACS catalysis · 2021Article
- Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis.Organic letters · 2020Article
- Ring-opening carbonyl-olefin metathesis of norbornenes.Chemical science · 2020Article
- Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy.Journal of visualized experiments : JoVE · 2020Article
- Investigation of Lewis Acid-Carbonyl Solution Interactions via Infrared-Monitored Titration.The Journal of organic chemistry · 2020Article
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Authors and funding
4 authors.
Funding
Abstract
Iron(III)-catalyzed carbonyl-olefin ring-closing metathesis employs reactivity not typically observed in Lewis acid-catalyzed reactions. In converting a ketone with a pendant olefin into a cycloalkene and a simple carbonyl byproduct, the reaction requires the Lewis acid catalyst to differentiate between the carbonyl of the substrate and that of the byproduct. It is necessary to determine how this solution interaction imparts the desired reactivity to best employ this method. Herein, we report detailed kinetic, spectroscopic, and colligative measurements applied toward the identification of the solution structures of the active Fe(III) and Ga(III) carbonyl-olefin metathesis catalysts. These data are consistent with formation of Lewis acid-carbonyl pairs for both metal systems under stoichiometric conditions. However, they diverge in the presence of higher equivalents of carbonyl, with Fe(III) forming highly ligated complexes, and no observed change for Ga(III). These findings are consistent with the resting state identity of the Fe(III) metathesis catalyst changing over the course of the reaction.
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