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

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 tolera...

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Veröffentlicht in:Organic letters 2021-10, Vol.23 (19), p.7472-7476
Hauptverfasser: He, Fu-Sheng, Bao, Ping, Yu, Feiyan, Zeng, Ling-Hui, Deng, Wei-Ping, Wu, Jie
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Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02665