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Copper-Catalyzed Sulfonylation/Cyclization of Pent-4-ynamides toward Sulfonyl-Functionalized Pyrrol-2-ones

Danhua Wu, Menglu Jiang, Juanjuan Wang, Wei Yu

2023Organic Letters11 citationsDOI

Abstract

A domino sulfonylation/intramolecular C–N coupling/dehydrogenation reaction was realized between pent-4-ynamides and sulfonyl chlorides by catalysis of Cu(acac) 2 and 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthalene. The reaction provides a convenient approach to sulfonyl-functionalized pyrrol-2-ones. This method can also be applied to the synthesis of 3-alkylidene isoindolinones from 2-ethynyl-benzamides.

Topics & Concepts

SulfonylChemistryCatalysisCopperMedicinal chemistryCombinatorial chemistryOrganic chemistryAlkylSulfur-Based Synthesis TechniquesCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods
Copper-Catalyzed Sulfonylation/Cyclization of Pent-4-ynamides toward Sulfonyl-Functionalized Pyrrol-2-ones | Litcius