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Toward Homogeneous Brønsted-Acid-Catalyzed Intramolecular Carbonyl-Olefin Metathesis Reactions.

The carbonyl-olefin metathesis (COM) reaction is an attractive approach for the formation of a new carbon-carbon double bond from a carbonyl precursor. In principle, this reaction can be promoted by… Click to show full abstract

The carbonyl-olefin metathesis (COM) reaction is an attractive approach for the formation of a new carbon-carbon double bond from a carbonyl precursor. In principle, this reaction can be promoted by the activation of the carbonyl group with a Brønsted acid catalyst; however, it is often complicated as a result of unwanted side reactions under acidic conditions. Thus, there have been only a very few examples of Brønsted-acid-catalyzed COM reactions, all of which required specially designed setups. Herein, we report a new practical homogeneous Brønsted-acid-catalyzed protocol using nitromethane, a readily available solvent, to promote intramolecular ring-closing COM reactions.

Keywords: homogeneous nsted; olefin metathesis; carbonyl; carbonyl olefin; nsted acid; acid catalyzed

Journal Title: Organic letters
Year Published: 2022

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