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Copper-Catalyzed Regioselective 1,4-Selenosulfonylation of 1,3-Enynes to Access Cyanoalkylsulfonylated Allenes

Fu‐Sheng He, Ping Bao, Feiyan Yu, Linghui Zeng, Wei‐Ping Deng, Jie Wu

2021Organic Letters83 citationsDOI

Abstract

By employing CuOAc as the catalyst, we realize a four-component reaction of 1,3-enynes, diselenides, DABCO·(SO2)2, and cycloketone oxime esters, providing facile access to diverse cyanoalkylsulfonylated allenyl selenides in moderate to good yields. This reaction features high functional group tolerance and a broad substrate scope, enabling the regioselective, sequential formation of C–SO2 and C–Se bonds under mild reaction conditions. Moreover, the utility of this methodology is further illustrated through the late-stage functionalization of drug-based molecules.

Topics & Concepts

RegioselectivityChemistryDABCOCatalysisFunctional groupSubstrate (aquarium)Combinatorial chemistryReaction conditionsMoleculeOximeOrganic chemistryGeologyPolymerOceanographySulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsOrganoselenium and organotellurium chemistry