Etherification of Phenols by Amines via Transient Diazonium Intermediates

In this paper, the synthesis of alkyl aryl ethers from electron poor phenols and amines, using 1,3-propanedinitrite, is described. Due to the mild conditions, functionalized primary, secondary, and tertiary alkyl groups were successfully introduced, denoting a highly tolerant process that allows for unprotected alcohols and acetals. The reaction is thought to proceed through the formation of a diazonium intermediate that undergoes subsequent S(N)2 or S(N)1 reactions.