Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons

We here report a catalytic strategy to enable the decarboxylative allylic amination of vinyl cyclic carbonates using various aliphatic and nucleophilic amines. The use of a protic medium and chelating diphosphine ligands is a main driver towards chemo-selective allylic amine formation, thereby minim...

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Detalhes bibliográficos
Autores: Gao, Fengyun, Ghorai, Debasish, Benet-Buchholz, Jordi, Kleij, Arjan W.
Tipo de documento: artigo
Estado:Versión aceptada para publicación
Data de publicação:2024
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/537803
Acesso em linha:http://hdl.handle.net/2072/537803
https://doi.org/10.1002/adsc.202400685
Access Level:Acceso aberto
Palavra-chave:Química
54 - Química
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spelling Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl SynthonsGao, FengyunGhorai, DebasishBenet-Buchholz, JordiKleij, Arjan W.Química54 - QuímicaWe here report a catalytic strategy to enable the decarboxylative allylic amination of vinyl cyclic carbonates using various aliphatic and nucleophilic amines. The use of a protic medium and chelating diphosphine ligands is a main driver towards chemo-selective allylic amine formation, thereby minimizing undesired ligand-driven complex speciation and aminolysis of the involved substrate. This improved approach amplifies the repertoire of allylic amine synthons that can be prepared from a variety of substrate combinations.Wiley-VCH2024info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion9 p.application/pdfhttp://hdl.handle.net/2072/537803https://doi.org/10.1002/adsc.202400685RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésCERCA Program/Generalitat de CatalunyaICREAMinisterio de Ciencia e Innovación (PID2020-112684GB-100, and Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-S)AGAUR (2021-SGR-00853).FG thanks the Chinese Research Council (CSC) for a predoctoral fellowship (2021-06180010)DG appreciates postdoctoral funding from AGAUR (2018-BP-00243) and AEI (PCI2021-122021-2B)CC-BY 4.0info:eu-repo/semantics/openAccessoai:recercat.cat:2072/5378032026-05-29T05:05:01Z
dc.title.none.fl_str_mv Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons
title Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons
spellingShingle Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons
Gao, Fengyun
Química
54 - Química
title_short Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons
title_full Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons
title_fullStr Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons
title_full_unstemmed Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons
title_sort Pd-Catalyzed Allylic Substitution using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons
dc.creator.none.fl_str_mv Gao, Fengyun
Ghorai, Debasish
Benet-Buchholz, Jordi
Kleij, Arjan W.
author Gao, Fengyun
author_facet Gao, Fengyun
Ghorai, Debasish
Benet-Buchholz, Jordi
Kleij, Arjan W.
author_role author
author2 Ghorai, Debasish
Benet-Buchholz, Jordi
Kleij, Arjan W.
author2_role author
author
author
dc.subject.none.fl_str_mv Química
54 - Química
topic Química
54 - Química
description We here report a catalytic strategy to enable the decarboxylative allylic amination of vinyl cyclic carbonates using various aliphatic and nucleophilic amines. The use of a protic medium and chelating diphosphine ligands is a main driver towards chemo-selective allylic amine formation, thereby minimizing undesired ligand-driven complex speciation and aminolysis of the involved substrate. This improved approach amplifies the repertoire of allylic amine synthons that can be prepared from a variety of substrate combinations.
publishDate 2024
dc.date.none.fl_str_mv 2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/537803
https://doi.org/10.1002/adsc.202400685
url http://hdl.handle.net/2072/537803
https://doi.org/10.1002/adsc.202400685
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv CERCA Program/Generalitat de Catalunya
ICREA
Ministerio de Ciencia e Innovación (PID2020-112684GB-100, and Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-S)
AGAUR (2021-SGR-00853)
.FG thanks the Chinese Research Council (CSC) for a predoctoral fellowship (2021-06180010)
DG appreciates postdoctoral funding from AGAUR (2018-BP-00243) and AEI (PCI2021-122021-2B)
dc.rights.none.fl_str_mv CC-BY 4.0
info:eu-repo/semantics/openAccess
rights_invalid_str_mv CC-BY 4.0
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 9 p.
application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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