28487-18-5Relevant articles and documents
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Burger et al.
, p. 3175 (1952)
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Lewis acid activation of pyridines for nucleophilic aromatic substitution and conjugate addition
Abou-Shehada, Sarah,Teasdale, Matthew C.,Bull, Steven D.,Wade, Charles E.,Williams, Jonathan M. J.
, p. 1083 - 1087 (2015/03/30)
A clean, mild and sustainable method for the functionalization of pyridines and their analogues is reported. A zinc-based Lewis acid is used to activate pyridine and its analogues towards nucleophilic aromatic substitution, conjugate addition, and cyclization reactions by binding to the nitrogen on the pyridine ring and activating the pyridine ring core towards further functionalization.
Anti-Markonikov reactions, 6. Rhodium-catalyzed amination of vinylpyridines: Hydroamination versus oxidative amination
Beller, Matthias,Trauthwein, Harald,Eichberger, Martin,Breindl, Claudia,Mueller, Thomas E.
, p. 1121 - 1132 (2007/10/03)
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.
