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Rhodium‐Catalyzed Amination of Vinylpyridines: Hydroamination versus Oxidative Amination
Author(s) -
Beller Matthias,
Trauthwein Harald,
Eichberger Martin,
Breindl Claudia,
Müller Thomas E.
Publication year - 1999
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199907)1999:7<1121::aid-ejic1121>3.0.co;2-8
Subject(s) - hydroamination , amination , chemistry , rhodium , cationic polymerization , cyclooctadiene , morpholine , regioselectivity , catalysis , organic chemistry , oxidative addition , medicinal chemistry
Cationic rhodium complexes catalyze the amination of 2‐ and 4‐vinylpyridine with secondary amines. Depending on the substrate and the reaction conditions either oxidative amination to yield the corresponding enamines 1a–8a or hydroamination to give 2‐aminoethylpyridines 1b–8b occurs. In all cases products with anti‐Markovnikov regioselectivity are obtained. For mechanistic studies novel cationic complexes of rhodium(I)‐containing cyclooctadiene and vinylpyridine 12 as well as complexes containing cyclooctadiene, vinylpyridine, and morpholine 13 were prepared and characterized by NMR spectroscopy and X‐ray diffraction analysis.