Velasco Rubio, ÁlvaroVarela Carrete, Jesús ÁngelSaá Rodríguez, Carlos2020-10-052021-05-012020Velasco-Rubio, A., Varela, J. A., Saá, C. (2020). Palladium-Catalyzed [5+2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines. Org. Lett., 22, 9, 3591-35951523-7060http://hdl.handle.net/10347/23358NOTICE: This is the peer reviewed version of the following article: Velasco-Rubio, A., Varela, J. A., Saá, C. (2020). Palladium-Catalyzed [5+2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines. Org. Lett., 22, 9, 3591-3595. [doi: 10.1021/acs.orglett.0c01053]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archivingPhenethyltriflamides react with 1,3-dienes upon treatment with a catalytic amount of Pd(OAc)2 and Cu(OAc)2/O2 as oxidant to afford chemo-, regio- and diastereoselectively 2,3,4,5-tetrahydro-1H-benzo[d]azepines (3-benzazepine derivatives) in good to excellent yields. A DFT study of the [5+2] heteroannulation suggests a mechanistic pathway starting by the formation of the six-membered palladacycle cis-PdX2L2 via a CMD process followed by η2 coordination and insertion of the 1,3-diene unit in a diastereoselective manner.engCopyright © 2020 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving3-Benzazepines1,3-Dienes[5+2] HeteroannulationPalladiumPhenethylamidesjournal article10.1021/acs.orglett.0c010531523-7052open access