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Base-Catalyzed Intramolecular Defluorination/O-Arylation Reaction for the Synthesis of 3-Fluoro-1,4-oxathiine 4,4-Dioxide

Lei Kang, Jinlong Zhang, Huameng Yang, Jinlong Qian*, Gaoxi Jiang*

*Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China, Email: q124802q163.com, gxjianglicp.cas.cn

L. Kang, J. Zhang, H. Yang, J. Qian, G. Jiang, Synlett, 2021, 32, 785-789.

DOI: 10.1055/a-1387-8862 (free Supporting Information)


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Abstract

A base-catalyzed intramolecular defluorination/O-arylation of readily available α-fluoro-β-one-sulfones provides a series of 3-fluoro-1,4-oxathiine 4,4-dioxide derivatives in very good yields. This process is triggered by a catalytic amount of tetramethylguanidine (TMG) as base and molecular sieves as both an adsorbent to remove HF acid and an activator to assist C-F bond cleavage.


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Key Words

base catalysis, defluorination, O-arylation, metal-free reactions, 1,4-oxathiines, benzo-fused S-heterocycles, benzo-fused O-heterocycles


ID: J72-Y2021