Ring-closing carbonyl-olefin metathesis (COM) reactions provide a straightforward method for producing cyclic alkenes from precursors containing carbonyl functional groups tethered to nucleophilic alkenes. COM reactions typically require high temperatures or catalysis to go to completion. Recently, several methods for carrying out Lewis-acid catalyzed COM reactions were reported; however, many of these methods necessitate the use of anhydrous solvents and inert atmospheres that complicate reaction setup. Herein we describe our efforts to optimize Bronsted-Lowry acid-catalyzed COM reactions on a variety of aldehyde- and ketone-containing substrates. Our preliminary results indicate that phosphoric acid-derived organocatalysts mediate reactions set up in open air with non-dried glassware and solvents, which significantly simplifies the reaction procedure compared to other reported methods. Moreover, these organocatalyts can be recovered from reaction mixtures and purified for re-use. We anticipate that our propsed research will result in a method for synthesizing cyclic alkenes that serves as an attractive complement to currently reported COM methods.

Organocatalyzed carbonyl-olefin metathesis: Exploring catalyst reactivity and substrate scope

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ACS Fall 2022

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