Synthesis of 3-benzylidenetetrahydrofurans: Tf2O-catalyzed hydroxylation/cyclization of cyclopropanemethanols with DMSO

Zhenjie Qi; Hongchen Wang; Yi Ren; Yanning Niu; Yong Jiang; Rulong Yan

doi:10.1039/D0CC07002E

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Synthesis of 3-benzylidenetetrahydrofurans: Tf₂O-catalyzed hydroxylation/cyclization of cyclopropanemethanols with DMSO†

Zhenjie Qi,‡^a Hongchen Wang,‡^a Yi Ren,^a Yanning Niu,^b Yong Jiang

^c and Rulong Yan

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, Key laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, China
E-mail: yanrl@lzu.edu.cn
Fax: +86 931-8912596

^b Department of Teaching and Research, Nanjing Forestry University, Huaian, China

^c School of Chemistry and Chemical Engineering, Yangtze Normal University, Chongqing, China

Abstract

A formal hydroxylation/cyclization of cyclopropanemethanols with DMSO is described, which involves isomerization and cyclization under Tf₂O catalysis. This reaction undergoes ring-opening of the cyclopropane moiety to generate homoallylic alcohols, which react with DMSO to produce 3-benzylidenetetrahydrofurans. With various substituted groups on cyclopropanemethanols the reactions proceed smoothly and the desired 3-benzylidenetetrahydrofurans are obtained in moderate to good yields.

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Article information

DOI: https://doi.org/10.1039/D0CC07002E
Article type: Communication
Submitted: 21 Oct 2020
Accepted: 18 Nov 2020
First published: 19 Nov 2020

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Chem. Commun., 2020,56, 15627-15630

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Synthesis of 3-benzylidenetetrahydrofurans: Tf₂O-catalyzed hydroxylation/cyclization of cyclopropanemethanols with DMSO

Z. Qi, H. Wang, Y. Ren, Y. Niu, Y. Jiang and R. Yan, Chem. Commun., 2020, 56, 15627 DOI: 10.1039/D0CC07002E

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