Issue 94, 2021

Synthesis of β-cyanoalkylsulfonylated vinyl selenides through a four-component reaction

Abstract

A mild copper-catalyzed four-component selenosulfonylation of alkynes, cycloketone oxime esters, DABCO (SO2)2 and diselenides has been developed. This method enables the rapid assembly of β-cyanoalkylsulfonylated vinyl selenides in moderate to good yields. Advantages of this protocol include a broad substrate scope, good functional group tolerance and the late-stage functionalization of complex molecules. Moreover, the potential utility of this methodology is demonstrated through simple oxidation of the products to access synthetically important alkynyl sulfones. Mechanistic studies suggest that a cyanoalkylsulfonyl radical intermediate is involved in this process.

Graphical abstract: Synthesis of β-cyanoalkylsulfonylated vinyl selenides through a four-component reaction

Supplementary files

Article information

Article type
Communication
Submitted
08 10 2021
Accepted
27 10 2021
First published
28 10 2021

Chem. Commun., 2021,57, 12603-12606

Synthesis of β-cyanoalkylsulfonylated vinyl selenides through a four-component reaction

F. He, Y. Yao, Z. Tang, Y. Qiu, W. Xie and J. Wu, Chem. Commun., 2021, 57, 12603 DOI: 10.1039/D1CC05690E

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