Issue 100, 2024

Rhodium-catalyzed C–H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones

Abstract

A Rh(III)-catalyzed C–H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones was realized, which afforded various o-fluoroalkenylation β-ketosulfoxonium ylides with high Z-selectivity and diverse oxadiazolone fused-isoquinolines. This protocol featured mild conditions, broad substrate scope, and functional-group compatibility. In addition, scale-up synthesis, related applications and preliminary mechanistic explorations were also accomplished.

Graphical abstract: Rhodium-catalyzed C–H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones

Supplementary files

Article information

Article type
Communication
Submitted
22 Oct 2024
Accepted
20 Nov 2024
First published
21 Nov 2024

Chem. Commun., 2024,60, 15000-15003

Rhodium-catalyzed C–H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones

J. Song, Z. Yang, S. Fang, W. Chen, L. Ye, X. Liu and B. Shu, Chem. Commun., 2024, 60, 15000 DOI: 10.1039/D4CC05621C

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