Palladium-Catalyzed [5+2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines
| Autor: | Alvaro Velasco Rubio, CDMF FAPESP, Jesús A. Varela, Carlos Saa |
|---|---|
| Přispěvatelé: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares, Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Phenethylamides
Benzazepines Molecular Structure [5+2] Heteroannulation 010405 organic chemistry Organic Chemistry Dopaminergic chemistry.chemical_element Polyenes 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Catalysis 0104 chemical sciences 3-Benzazepines chemistry 1 3-Dienes Physical and Theoretical Chemistry Palladium |
| Zdroj: | Minerva: Repositorio Institucional de la Universidad de Santiago de Compostela Universidad de Santiago de Compostela (USC) Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela instname |
| Popis: | NOTICE: 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-archiving Phenethyltriflamides 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. This work has received financial support from MINECO (project CTQ2017-87939R and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03) and the European Union (European Regional Development Fund – ERDF). A.V.-R. thanks Xunta de Galicia for a predoctoral fel-lowship (ED481A-2018/34, 2018-2021) SI |
| Databáze: | OpenAIRE |
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