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Ruthenium-catalyzed oxidative coupling of primary amines with internal alkynes through C-H bond activation: scope and mechanistic studies

AuthorsRuiz Morte, Sara ; Villuendas, Pedro ; Ortuño, M. A.; Lledós, Agustí; Urriolabeitia, Esteban P.
Density functional calculations
Nitrogen heterocycles
Issue Date2015
CitationChemistry - A European Journal 21(23): 8626-8636 (2015)
AbstractThe oxidative coupling of primary amines with internal alkynes catalyzed by Ru complexes is presented as a general atom-economy methodology with a broad scope of applications in the synthesis of N-heterocycles. Reactions proceed through regioselective C-H bond activation in 15 minutes under microwave irradiation or in 24 hours with conventional heating. The synthesis of 2,3,5-substituted pyridines, benzo[h]isoquinolines, benzo[g]isoquinolines, 8,9-dihydro-benzo[de]quinoline, 5,6,7,8-tetrahydroisoquinolines, pyrido[3,4g]isoquinolines, and pyrido[4,3g]isoquinolines is achievable depending on the starting primary amine used. DFT calculations on a benzylamine substrate support a reaction mechanism that consists of acetate-assisted C-H bond activation, migratory-insertion, and C[BOND]N bond formation steps that involve 28–30 kcal mol−1. The computational study is extended to additional substrates, namely, 1-naphthylmethyl-, 2-methylallyl-, and 2-thiophenemethylamines.
Identifiersdoi: 10.1002/chem.201500338
issn: 0947-6539
e-issn: 1521-3765
Appears in Collections:(ISQCH) Artículos
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