Macrocyclization of 3-triflyloxybenzynes with tetrahydrofuran via an anionic thia-Fries rearrangement

Authors:Cheng, Ruixiang; Xiong, Wenfang; Qi, Chaorong*; Wang, Lu; Ren, Yanwei; Jiang, Huanfeng
Source:Chemical Communications, 2020, 56(48): 6495-6498.
DOI:10.1039/d0cc00135j

Summary

A novel and uncommon macrocyclization reaction between 3-triflyloxybenzynes and tetrahydrofuran has been developed for the first time, providing a direct method for the synthesis of a range of functionalized 19-membered polyether macrocycles in moderate to good yields. The process was proposed to proceed through an anionic thia-Fris rearrangement under transition metal-free conditions, leading to the formation of four new C-O bonds and one new C-S bond in a single step.

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