Cargando…
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...
Autores principales: | , , |
---|---|
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 |
_version_ | 1784578255585542144 |
---|---|
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. |
format | Online Article Text |
id | pubmed-8488958 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT vidalxandro assemblyoftetrahydroquinolinesand2benzazepinesbypdcatalyzedcycloadditionsinvolvingtheactivationofcsp3hbonds AT mascarenasjoseluis assemblyoftetrahydroquinolinesand2benzazepinesbypdcatalyzedcycloadditionsinvolvingtheactivationofcsp3hbonds AT guliasmoises assemblyoftetrahydroquinolinesand2benzazepinesbypdcatalyzedcycloadditionsinvolvingtheactivationofcsp3hbonds |