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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/107929
Preparation of substituted tetrahydroisoquinolines by Pd(II)-catalyzed NH2-directed insertion of Michael acceptors into C-H bonds followed by NH2-conjugated additions
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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.
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MANCINELLI, Andrea, et al. Preparation of substituted tetrahydroisoquinolines by Pd(II)-catalyzed NH2-directed insertion of Michael acceptors into C-H bonds followed by NH2-conjugated additions. Organometallics. 2017. Vol. 36, num. 4, pags. 911-919. ISSN 0276-7333. [consulted: 13 of June of 2026]. Available at: https://hdl.handle.net/2445/107929