Deoxygenative Intramolecular Etherification of Alkyl Diols

Abstract

Ethers are a ubiquitous functional group in natural products and drug compounds due to their high stability and mild polarity. However, robust synthetic methods to access ether functionalities with wide functional group tolerance remain scarce. Herein, a method to synthesize dialkyl ethers from aliphatic diols under mild conditions is disclosed, utilizing N-heterocyclic carbene reagents to generate alkyl radicals from alcohols and copper catalysis for C O bond formation. Studies were conducted on the mechanism of this reaction that indicate a triplet sensitization cycle is operative, and a preliminary isolated scope is presented.