A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines

Abstract

summary, we have developed a facile and general catalytic method for the conversion of aryl bromides to arylamines, which works well for inter- and intramolecular processes. Particularly noteworthy features of this method include the experimental sim- plicity, the tin/boron-free conditions, and the broad substrate scope. Efforts to discover improved catalyst systems which op- erate under milder reaction conditions as well as to employ these methods in synthetic organic chemistry are in progress.[13, l4] Esper imen tal Procedure 3: A mixture of 2-bromonaphthalene (205 mg. 0.99 mmol), N-niethylhomoveratry- lamine (234 mg, 1.20 mmol), sodium rert-hutoxide (134 mg. 1.39 mmol) and [Pd- CI,(P(o-tolyl),),] (14 mg. 0.02 mmol) in toluene (8-9 mL) was heated under argon at 100 C for 3 h. Aftercooling to room temperature, the reaction mixture was taken up in Et,O (30-40 mL) and washed with brine (15-20 mL). The organic fraction was dried with MgSO,, and concentrated using a rotary evaporator. The crude material was purified by flash chromatography on silica gel using hexane (100 mL), 1iexane:EtOAc