Organic letters

Preparation of aryl-alkylamines via electrophilic amination of functionalized arylazo tosylates with alkylzinc reagents

P Sinha, CC Kofink, P Knochel

Index: Sinha, Pradipta; Kofink, Christiane C.; Knochel, Paul Organic Letters, 2006 , vol. 8, # 17 p. 3741 - 3744

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Citation Number: 29

Abstract

A new electrophilic amination reaction of functionalized arylazo tosylates with alkylzinc halides or dialkylzinc reagents in THF leads to the corresponding hydrazines. A facile cleavage of the NN bond is achieved using Raney nickel in refluxing ethanol, leading to substituted secondary aryl-alkylamines in 45-79% yield.