Direct substitution of aromatic ethers by lithium amides. A new aromatic amination reaction

W ten Hoeve, CG Kruse, JM Luteyn…

Index: Hoeve, Wolter ten; Kruse, Chris, G.; Luteyn, Jan M.; Thiecke, Janet R. G.; Wynberg, Hans Journal of Organic Chemistry, 1993 , vol. 58, # 19 p. 5101 - 5106

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Citation Number: 50

Abstract

Reaction of lithiated dialkylamines with methoxy aromatics in refluxing THF leads to products resulting from a direct ipso-substitution. Especially with lithiated secondary amines high conversions and selectivities are achieved. Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a competing pathway via aryne intermediates. The scope and mechanistic implications of this novel nucleophilic ...