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

Ruixiang Cheng; Wenfang Xiong; Chaorong Qi; Lu Wang; Yanwei Ren; Huanfeng Jiang

doi:10.1039/d0cc00135j

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

Chem Commun (Camb). 2020 Jun 16;56(48):6495-6498. doi: 10.1039/d0cc00135j.

Authors

Ruixiang Cheng¹, Wenfang Xiong¹, Chaorong Qi², Lu Wang¹, Yanwei Ren¹, Huanfeng Jiang¹

Affiliations

¹ Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. crqi@scut.edu.cn.
² Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China. crqi@scut.edu.cn and State Key Lab of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, P. R. China.

PMID: 32409790
DOI: 10.1039/d0cc00135j

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.