Regioselective Alkylacylation of 1,3-Dienes by Merging -Heterocyclic Carbene Catalysis with Photoinduced Palladium Catalysis.

Org Lett

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Published: January 2025

Herein, we develop a dual catalytic platform for the 1,2- or 1,4-alkylacylation reaction of 1,3-dienes with readily available alkyl halides and aldehydes by merging -heterocyclic carbene catalysis with photoinduced palladium catalysis. A series of β,γ-unsaturated ketones are obtained in good to high yields. Mechanistic studies suggest that this reaction involves a radical process. The direct synthesis of flavanone from salicylaldehyde exemplified the potential capability of this dual catalytic platform.

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http://dx.doi.org/10.1021/acs.orglett.4c04453DOI Listing

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