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Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp(3))–H Bonds

[Image: see text] Cycloaddition reactions are among the most practical strategies to assemble cyclic products; however, they usually require the presence of reactive functional groups in the reactants. Here, we report a palladium-catalyzed formal (4 + 2) cycloaddition that involves the activation of...

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Autores principales: Vidal, Xandro, Mascareñas, José Luis, Gulías, Moisés
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8488958/
https://www.ncbi.nlm.nih.gov/pubmed/34165984
http://dx.doi.org/10.1021/acs.orglett.1c01594
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author Vidal, Xandro
Mascareñas, José Luis
Gulías, Moisés
author_facet Vidal, Xandro
Mascareñas, José Luis
Gulías, Moisés
author_sort Vidal, Xandro
collection PubMed
description [Image: see text] Cycloaddition reactions are among the most practical strategies to assemble cyclic products; however, they usually require the presence of reactive functional groups in the reactants. Here, we report a palladium-catalyzed formal (4 + 2) cycloaddition that involves the activation of C(sp(3))–H bonds and provides a direct, unconventional entry to tetrahydroquinoline skeletons. The reaction utilizes amidotolyl precursors and allenes as annulation partners, and is catalyzed by Pd(II) precursors in combination with specific N-acetylated amino acid ligands. The reactivity can be extended to ortho-methyl benzylamides, which provide for the assembly of appealing tetrahydro-2-benzazepines in a formal (5 + 2) annulation process.
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spelling pubmed-84889582021-10-05 Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp(3))–H Bonds Vidal, Xandro Mascareñas, José Luis Gulías, Moisés Org Lett [Image: see text] Cycloaddition reactions are among the most practical strategies to assemble cyclic products; however, they usually require the presence of reactive functional groups in the reactants. Here, we report a palladium-catalyzed formal (4 + 2) cycloaddition that involves the activation of C(sp(3))–H bonds and provides a direct, unconventional entry to tetrahydroquinoline skeletons. The reaction utilizes amidotolyl precursors and allenes as annulation partners, and is catalyzed by Pd(II) precursors in combination with specific N-acetylated amino acid ligands. The reactivity can be extended to ortho-methyl benzylamides, which provide for the assembly of appealing tetrahydro-2-benzazepines in a formal (5 + 2) annulation process. American Chemical Society 2021-06-24 2021-07-16 /pmc/articles/PMC8488958/ /pubmed/34165984 http://dx.doi.org/10.1021/acs.orglett.1c01594 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Vidal, Xandro
Mascareñas, José Luis
Gulías, Moisés
Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp(3))–H Bonds
title Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp(3))–H Bonds
title_full Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp(3))–H Bonds
title_fullStr Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp(3))–H Bonds
title_full_unstemmed Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp(3))–H Bonds
title_short Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp(3))–H Bonds
title_sort assembly of tetrahydroquinolines and 2-benzazepines by pd-catalyzed cycloadditions involving the activation of c(sp(3))–h bonds
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8488958/
https://www.ncbi.nlm.nih.gov/pubmed/34165984
http://dx.doi.org/10.1021/acs.orglett.1c01594
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