Issue 13, 2022

Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates

Abstract

We present herein an efficient photocatalytic transformation of vinyl fluorosulfates to aromatic β-keto sulfonyl fluorides with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluorosulfates through a free fluorosulfonyl radical (FSO2˙). This methodology provides a facile approach to aromatic β-keto sulfonyl fluorides, featuring sustainable conditions and a broad substrate scope (32 examples) with 33%–90% isolated yields.

Graphical abstract: Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates

Supplementary files

Article information

Article type
Research Article
Submitted
14 mar 2022
Accepted
09 may 2022
First published
11 may 2022

Org. Chem. Front., 2022,9, 3540-3545

Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates

J. Cui, S. Ke, J. Zhao, S. Wu, W. Luo, S. Xu, X. Su and Y. Li, Org. Chem. Front., 2022, 9, 3540 DOI: 10.1039/D2QO00416J

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