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Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes. 2017
Borja Cendón, and
Noelia Casanova, and
Cezar Comanescu, and
Rebeca García-Fandiño, and
Andrés Seoane, and
Moisés Gulías, and
José L Mascareñas
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela , 15782 Santiago de Compostela, Spain.
2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C-H activation of the alkenylanilide involves a classical concerted metalation-deprotonation (CMD) mechanism.
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