Synthesis of α-Difluoromethylene Ethers via Photoredox-Induced Hyperconjugative Ring Opening of <i>gem</i>-Difluorocyclopropanes
Yu‐Rou Zhao, Zhiyong Ma, Le Liu, Pin Gao, Xin‐Hua Duan, Mingyou Hu
Abstract
Fluorinated compounds have found widespread applications in pharmaceuticals, agrochemicals, and materials science. Precise construction of α-difluoromethylene ether (CF 2 – O) moiety in organic molecules is of high demand. Herein, a visible light-promoted reaction protocol for the synthesis of α-difluoromethylene ether from gem -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.
Topics & Concepts
CyclopropaneMoietyRing (chemistry)EtherChemistryWilliamson ether synthesisMoleculeCombinatorial chemistryPhotochemistryOrganic chemistryFluorine in Organic ChemistryCyclopropane Reaction Mechanisms