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Synlett 2023; 34(05): 471-476
DOI: 10.1055/s-0041-1738692
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Special Edition Thieme Chemistry Journals Awardees 2022

Photo-organocatalytic Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Acetates

Peng Wang‡
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Fuzhou University, 350108 Fuzhou, P. R. of China
,
Shao-Jie Li‡
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Fuzhou University, 350108 Fuzhou, P. R. of China
,
Honghai Zhang
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Fuzhou University, 350108 Fuzhou, P. R. of China
,
Na Yang
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Fuzhou University, 350108 Fuzhou, P. R. of China
,
Saihu Liao  ∗
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Fuzhou University, 350108 Fuzhou, P. R. of China
b   Beijing National Laboratory for Molecular Sciences (BNLMS), Beijing 100190, P. R. of China
› Author AffiliationsWe gratefully acknowledge the Recruitment Program of Global Experts, the Beijing National Laboratory for Molecular Sciences, 100-Talent Program of Fujian, and Fuzhou University for financial support. We also thank the National Natural Science Foundation of China (No. 21602028).
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Abstract

A metal-free synthesis of useful β-keto sulfonyl fluorides has been established via radical fluorosulfonylation of ketone-derived vinyl acetates under photoredox organocatalysis by using 1-fluorosulfonyl benzoimidazolium (FABI) as the fluorosulfonyl radical source and oxygen-doped anthanthrene (ODA) as the photocatalyst. A series of aryl and alkyl β-keto sulfonyl fluorides as well as cyclic analogues can be readily obtained in moderate to high yields from widely available ketone starting materials.

Key words

sulfonyl fluorides - radical fluorosulfonylation - vinyl acetates - photoredox - organocatalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738692.
  • Supporting Information


Publication History

Received: 30 June 2022

Accepted after revision: 09 August 2022

Article published online:
09 September 2022

© 2022. Thieme. All rights reserved

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