Issue 92, 2021

Selective synthesis of enol ethers via nickel-catalyzed cross coupling of α-oxy-vinylsulfones with alkylzinc reagents

Abstract

We describe here a Ni-catalyzed Negishi coupling reaction to prepare 1,2-dialkyl enol ethers in a stereoconvergent fashion. This method employs readily available and bench-stable α-oxy-vinylsulfones as electrophiles. The C–sulfone bond in the α-oxy-vinylsulfone motif is cleaved chemoselectively in these reactions. The mild conditions are tolerant of a variety of functional groups on both partners, thus representing a general strategy for enol ether synthesis. This unique reactivity of α-oxy-vinylsulfones indicates their further application as electrophilic partners in cross-coupling reactions.

Graphical abstract: Selective synthesis of enol ethers via nickel-catalyzed cross coupling of α-oxy-vinylsulfones with alkylzinc reagents

Supplementary files

Article information

Article type
Communication
Submitted
23 Sept. 2021
Accepted
19 Okt. 2021
First published
20 Okt. 2021

Chem. Commun., 2021,57, 12273-12276

Selective synthesis of enol ethers via nickel-catalyzed cross coupling of α-oxy-vinylsulfones with alkylzinc reagents

L. Gong, Q. Zhang, D. Xie, W. Zhang, S. Xu, X. Zhang and D. Niu, Chem. Commun., 2021, 57, 12273 DOI: 10.1039/D1CC05347G

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