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

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3741-3744

  Sinha, Pradipta ^a   Kofink, Christiane C ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

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EID: 33748611081     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061303m     Document Type: Article

References (39)

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39. Typical procedure: preparation of cyclopentyl-(3,5-dimethyphenyl)-amine 3g. In a flame-dried argon-flushed 25 mL two-neck round-bottom flask equipped with a magnetic stirrer and septum, cyclopentylzinc iodide 2a (0.92 mL, 1.2 mmol, 1.31 M in THF) was dissolved in dry THF (1 mL) and cooled to -20 °C. 3.5-Dimethylphenylazo tosylate 1d (288 mg, 1.0 mmol) was dissolved in dry THF (2 mL) and added dropwise to the organozinc reagent. The reaction mixture was stirred at -20 °C for 30 min to form the intermediate zinc hydrazide. The solvent was removed, and the residue was dissolved in ethanol (5 mL). Raney nickel (activated catalyst 50%, in water; Acros Chemical) (2.5 g) was added, and the reaction mixture was refluxed for 1.5 h. The reaction mixture was allowed to cool to room temperature, and the Raney nickel residue was separated by filtration. Ethanol was removed in vacuo and the residue extracted with diethyl ether (2 × 10 mL), washed with brine (2 × 10 mL), and dried over sodium sulfate. Purification by flash chromatography (n-pentane/diethyl ether 99: 1) yielded 144 mg (76% isolated yield) of 3g as a light-yellow viscous liquid.