Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl Halides

• Published in: Journal of the American Chemical Society Vol. 128; no. 31; pp. 10028 - 10029
• Main Authors: Shen, Qilong, Hartwig, John F
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 09-08-2006
• Subjects: Amides - chemistry; Ammonia - chemistry; Catalysis; Chemistry; Exact sciences and technology; Halogens - chemistry; Lithium - chemistry; Noncondensed benzenic compounds; Organic chemistry; Palladium - chemistry; Preparations and properties; Ammonia; Catalytic reaction; Transition element complexes; Haloarene; Carboxamide; Lithium; Palladium complex; Platinoid Complexes
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja064005t

A mild, palladium-catalyzed coupling of aryl halides with ammonia or lithium amide to form primary arylamines as the major product is described. These reactions occurred with excellent selectivity for formation of the primary arylamine over formation of the diarylamine (9.5:1 to over 50:1 ratios of arylamine to diarylamine). In addition, the first organopalladium complex with a terminal −NH2 ligand has been isolated. This complex reductively eliminates to form arylamines.