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 oct. 2021
First published
20 oct. 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

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