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

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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… Click to show full 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.

Keywords: enynes access; selenosulfonylation enynes; regioselective selenosulfonylation; catalyzed regioselective; access; copper catalyzed

Journal Title: Organic letters
Year Published: 2021

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