Metal-Free Etherification of Aryl Methyl Ether Derivatives by C-OMe Bond Cleavage

Article abstract of DOI:10.1021/acs.orglett.8b01696

A general and efficient protocol was developed for the synthesis of aryl alkyl ethers through metal-free C-OMe bond cleavage under mild reaction conditions. This process displays a wide scope of methoxyarenes and alcohols, including primary, secondary, and tertiary alcohols, as well as natural products, pharmaceuticals, and biologically active alcohols. DFT calculations and experimental results simultaneously confirm that a potassium ion plays a critical role in the activation of methoxy group via binding with the nitrile and provide support for an S_NAr mechanism.