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Preparation of substituted tetrahydroisoquinolines by Pd(II)-catalyzed NH2-directed insertion of Michael acceptors into C-H bonds followed by NH2-conjugated additions
Mancinelli, Andrea; Alamillo, Carla; Albert Mach, Joan; Ariza Piquer, Xavier; Etxabe, Haizea; Farràs i Soler, Jaume; García Gómez, Jordi; Granell Sanvicente, Jaime Ramón; Quijada, F. Javier
Universitat de Barcelona
3,3-Disubstituted tetrahydroisoquinolines are prepared in one step from Michael acceptors and 2-phenylethylamines under Pd catalysis and Ag2CO3 as an oxidant. Presumably, activation of an ortho C-H bond of the aromatic ring with Pd(II) is directed by the primary amine to form a palladacycle. Insertion of the olefin, subsequent conjugated addition of the amine, and reductive elimination of Pd(0) affords the expected products. Silver carbonate is not necessary when 2-phenylethylamines are converted previously to N-benzoyloxy-2-phenylethylamines.
Compostos heterocíclics
Pal·ladi (Element químic)
Catàlisi
Heterocyclic compounds
Palladium
Catalysis
cc-by-nc (c) American Chemical Society , 2017
http://creativecommons.org/licenses/by-nc/3.0/es
Artículo
info:eu-repo/semantics/publishedVersion
American Chemical Society
         

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