Chemoselective Ru-Catalyzed Oxidative Lactamization vs Hydroamination of Alkynylamines: Insights from Experimental and Density Functional Theory Studies
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ISSN: 0022-3263
E-ISSN: 1520-6904
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American Chemical Society
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Abstract
The Ru-catalyzed intramolecular oxidative amidation (lactamization) of aromatic alkynylamines with 4-picoline N-oxide as an external oxidant has been developed. This
chemoselective process is very efficient to achieve medium-sized ε- and ζ-lactams (seven- and eight-membered rings) but not for the formation of common δ-lactams (six-membered rings). DFT studies unveiled the capital role of the chain length between the amine and the alkyne functionalities: the longer the connector, the more favored the lactamization process vs hydroamination.
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Álvarez-Constantino, A., Álvarez-Pérez, A., Varela, J. A., Sciortino, G., Ujaque, G., Saá, C. (2023). Chemoselective Ru-Catalyzed Oxidative Lactamization vs Hydroamination of Alkynylamines: Insights from Experimental and Density Functional Theory Studies. J. Org. Chem., 88, 2, 1185-193
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https://doi.org/10.1021/acs.joc.2c02770Sponsors
This work has received financial support from MICINN (projects PID2020-118048GB-I00, PID2020-116861GB-I00, and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2022/27, Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03), and the European Union (European Regional Development Fund)
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© 2021 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/)