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

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Abstract

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.

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

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Article information


Submitted
07 Jan 2020
Accepted
04 May 2020
First published
04 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

R. Cheng, W. Xiong, C. Qi, L. Wang, Y. Ren and H. Jiang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00135J

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