Preparation of Aryl−Alkylamines via Electrophilic Amination of Functionalized Arylazo Tosylates with Alkylzinc Reagents

[reaction: see text] 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 N-N bond is achieved using Raney nickel in refluxing ethanol, leading to substituted secondary aryl-alkylamines in 45-79% yield.