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 Okt 2021
Accepted
27 Okt 2021
First published
28 Okt 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements