Rhodium-Catalyzed Amination of Vinylpyridines: Hydroamination versus Oxidative Amination

✍ Scribed by Matthias Beller; Harald Trauthwein; Martin Eichberger; Claudia Breindl; Thomas E. Müller

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 378 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-1948
• DOI: 10.1002/(sici)1099-0682(199907)1999:7<1121::aid-ejic1121>3.0.co;2-8

✦ Synopsis

Cationic rhodium complexes catalyze the amination of 2-and regioselectivity are obtained. For mechanistic studies novel cationic complexes of rhodium(I)-containing cyclooctadiene 4-vinylpyridine with secondary amines. Depending on the substrate and the reaction conditions either oxidative and vinylpyridine 12 as well as complexes containing cyclooctadiene, vinylpyridine, and morpholine 13 were amination to yield the corresponding enamines 1a؊8a or hydroamination to give 2-aminoethylpyridines 1b؊8b prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. occurs. In all cases products with anti-Markovnikov amination of olefins occurs, we became interested in the