Synthesis of α-Difluoromethylene Ethers via Photoredox-Induced Hyperconjugative Ring Opening of -Difluorocyclopropanes.

J Org Chem

School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, Xi'an Jiaotong University, Xi'an 710049, China.

Published: March 2023

Fluorinated compounds have found widespread applications in pharmaceuticals, agrochemicals, and materials science. Precise construction of α-difluoromethylene ether (CFO) moiety in organic molecules is of high demand. Herein, a visible light-promoted reaction protocol for the synthesis of α-difluoromethylene ether from -difluorocyclopropane is described. The key ring-opening step is induced by hyperconjugative interaction of cyclopropane with photo-oxidized aromatic rings. This reaction is easy scale-up, and the products bearing a synthetic handle enable their further manipulation.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.2c03062DOI Listing

Publication Analysis

Top Keywords

synthesis α-difluoromethylene
8
α-difluoromethylene ether
8
α-difluoromethylene ethers
4
ethers photoredox-induced
4
photoredox-induced hyperconjugative
4
hyperconjugative ring
4
ring opening
4
opening -difluorocyclopropanes
4
-difluorocyclopropanes fluorinated
4
fluorinated compounds
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!