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Synthesis 2024; 56(11): 1727-1734
DOI: 10.1055/s-0042-1751535
paper
New Trends in Organic Synthesis from Chinese Chemists

FSO2 Radical-Initiated Photoredox Cyclization of 4-Enoic Acids to Functionalized γ-Lactones

Xin Fang
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
,
Xuebing Geng
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
,
Peng Wang
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
b   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
,
Honghai Zhang
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
c   State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, P. R. China
,
Saihu Liao  ∗
a   Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P. R. China
c   State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, P. R. China
› Author AffiliationsWe gratefully acknowledge the Recruitment Program of Global Experts, and the 100-talent project of Fujian, Fuzhou University, and Xiamen University for the financial support.
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Abstract

The incorporation of sulfonyl fluoride groups into molecules has been proven effective in enhancing their biological activities or introducing new functions. Herein, a transition-metal-free and visible-light-mediated radical tandem cyclization of unsaturated carboxylic acid is reported. This affords a facile access to FSO2-functionalized γ-lactones efficiently, which are critical structural motifs widely present in biologically active molecules.

Key words

FSO2 radical - photoredox - γ-lactone - cyclization - difunctionlization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751535.
  • Supporting Information


Publication History

Received: 08 September 2023

Accepted after revision: 14 November 2023

Article published online:
19 December 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
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