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Cooperative Photoredox- and Nickel-Catalyzed Alkylative Cyclization Reactions of Alkynes with 4-Alkyl-1,4-dihydropyridines

Yulin Zhang, Yoshiaki Tanabe, Shogo Kuriyama, Yoshiaki Nishibayashi

2021The Journal of Organic Chemistry20 citationsDOI

Abstract

Cooperative photoredox- and nickel-catalyzed alkylative cyclization reactions of iodoalkynes with 4-alkyl-1,4-dihydropyridines as alkylation reagents under visible light irradiation have been achieved to afford the corresponding alkylated cyclopentylidenes in good to high yields. Introduction of substituents at the propargylic position of iodoalkynes has led to the stereoselective formation of E-isomers. The present reaction system provides a novel synthetic method for alkylative cyclization reactions of both terminal and internal alkynes with cooperative photoredox and nickel catalysis.

Topics & Concepts

ChemistryAlkylationReagentPhotoredox catalysisAlkylNickelCatalysisStereoselectivityCombinatorial chemistryOrganic chemistryPhotochemistryPhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions
Cooperative Photoredox- and Nickel-Catalyzed Alkylative Cyclization Reactions of Alkynes with 4-Alkyl-1,4-dihydropyridines | Litcius