DIRECT SUBSTITUTION OF AROMATIC ETHERS BY LITHIUM AMIDES - A NEW AROMATIC AMINATION REACTION

Reaction of lithiated dialkylamines with methoxy aromatics in refluxin g THF leads to products resulting from a direct ipso-substitution. Esp ecially with lithiated secondary amines high conversions and selectivi ties are achieved. Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a co mpeting pathway via aryne intermediates. The scope and mechanistic imp lications of this novel nucleophilic amination reaction are described.