p -Cresol-Enabled Nickel-Catalyzed Intermolecular Redox-Economical Coupling of Allyl Alcohols with Alkynes through oxa-Nickelacycle

An intermolecular redox-economical coupling reaction of allyl alcohols with alkynes, catalyzed by Ni-Brønsted acid cocatalysis, has been developed. This method allows for the synthesis of a diverse range of γ,δ-unsaturated ketones with yields ranging from 40% to 94%, while maintaining excellent comp...

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Veröffentlicht in:Organic letters 2023-12, Vol.25 (47), p.8463-8468
Hauptverfasser: Wang, Rong-Hua, Zhang, Zhou, Li, Bo, Zhu, Gao-Feng, Shi, Jing, Tang, Lei
Format: Artikel
Sprache:eng
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Zusammenfassung:An intermolecular redox-economical coupling reaction of allyl alcohols with alkynes, catalyzed by Ni-Brønsted acid cocatalysis, has been developed. This method allows for the synthesis of a diverse range of γ,δ-unsaturated ketones with yields ranging from 40% to 94%, while maintaining excellent compatibility with various functional groups. The transformation of the resulting product demonstrates the significant practical value of this method. Further mechanistic investigations have revealed that the reaction proceeds through the formation of an oxa-nickelacycle intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03320