A facile metal-free one-flask synthesis of multi-substituted furans via a BF3·Et2O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones

Zixin Zhang; Aimin Huang; Lin Ma; Jian-hua Xu; Min Zhang

doi:10.1039/D2RA01472F

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A facile metal-free one-flask synthesis of multi-substituted furans via a BF₃·Et₂O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones†

Zixin Zhang,^a Aimin Huang,^a Lin Ma,^a Jian-hua Xu^b and Min Zhang

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, China
E-mail: chemizhang@gxu.edu.cn

^b School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210093, China

Abstract

A facile, efficient and metal free one-flask approach to diversely substituted furans from easily accessible 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones is reported. This protocol integrates three steps of cyclopropanation, Cloke–Wilson rearrangement and elimination of HCl in one-flask to give products in moderate to good yields. It provides a metal and oxidant free approach to multi-substituted furans with the advantages of easy operation, mild reaction conditions and a broad scope of substrates.

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Article information

DOI: https://doi.org/10.1039/D2RA01472F
Article type: Paper
Submitted: 06 Mar 2022
Accepted: 11 May 2022
First published: 18 May 2022
This article is Open Access

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RSC Adv., 2022,12, 15190-15195

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A facile metal-free one-flask synthesis of multi-substituted furans via a BF₃·Et₂O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones

Z. Zhang, A. Huang, L. Ma, J. Xu and M. Zhang, RSC Adv., 2022, 12, 15190 DOI: 10.1039/D2RA01472F

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