Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes

A dual Co/photoredox catalytic coupling of 1,3-enynes and α,ß-unsaturated aliphatic aldehydes and ketones has been developed that creates access to highly functional 1,3-diene synthons through a regio- and stereoselective carbon-carbon coupling process. The scope of the process features diverse func...

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Autores: Tóth, Balázs L., Delgado, Alejandro, Ghorai, Debasish, Meneses, Diego, García-Camacho, Aimara, Vicent-Morales, Maria, Benet-Buchholz, Jordi, Funes-Ardoiz, Ignacio, Kleij, Arjan W.
Formato: artículo
Fecha de publicación:2025
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/489064
Acesso em linha:http://hdl.handle.net/2072/489064
https://doi.org/10.1002/anie.202522561
Access Level:acceso embargado
Palavra-chave:Química
54
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spelling Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-DienesTóth, Balázs L.Delgado, AlejandroGhorai, DebasishMeneses, DiegoGarcía-Camacho, AimaraVicent-Morales, MariaBenet-Buchholz, JordiFunes-Ardoiz, IgnacioKleij, Arjan W.Química54A dual Co/photoredox catalytic coupling of 1,3-enynes and α,ß-unsaturated aliphatic aldehydes and ketones has been developed that creates access to highly functional 1,3-diene synthons through a regio- and stereoselective carbon-carbon coupling process. The scope of the process features diverse functionalized scaffolds with a high degree of molecular complexity. The synthetic utility of these 1,3-dienes is demonstrated including a telescoped, one-pot approach using an alkynyl cyclic carbonate as a 1,3-enyne surrogate offering direct access to the 1,3-diene product. Mechanistic analysis involving control reactions, deuterium labeling studies and DFT calculations are in line with the in situ formation of a Co─H species and an outer-sphere coupling pathway in which a regio- and stereoselective coupling occurs between a dienyl radical and carbonyl species.info:eu-repo/semantics/acceptedVersionWiley2025info:eu-repo/semantics/article13 p.application/pdfhttp://hdl.handle.net/2072/489064https://doi.org/10.1002/anie.202522561RECERCAT (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 CatalunyaICREA FoundationMICIU/AEI (PID2023-149295NB-I00, RED2022-134074-T and Severo Ochoa Excellence Accreditation CEX2024-001469-S)AGAUR (2021-SGR-00853)B.L.T. acknowledges support from the European Union's Horizon 2020 research and innovation program under the Marie Skłodowska-Curie grant agreement 101026029A.D. thanks MICINN for a predoctoral fellowship (PRE2021-100384)A.G.-C and I.F.A thank MICIU/AEI/ 10.13039/501100011033 and Feder/EU for funding of the projects PID2021-126075NB-I00 and MICIU/AEI/10.13039/501100011033, and FSE + for a Ramón y Cajal fellowship (RYC2022–035776-I)A.G-C. thanks the University of La Rioja and La Rioja Government for a predoctoral fellowship within the 2025 call.Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/embargoedAccessoai:recercat.cat:2072/4890642026-05-29T05:05:01Z
dc.title.none.fl_str_mv Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes
title Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes
spellingShingle Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes
Tóth, Balázs L.
Química
54
title_short Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes
title_full Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes
title_fullStr Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes
title_full_unstemmed Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes
title_sort Dual Co/Photoredox-Catalyzed Regio- and Stereoselective Synthesis of Highly Functional 1,3-Dienes
dc.creator.none.fl_str_mv Tóth, Balázs L.
Delgado, Alejandro
Ghorai, Debasish
Meneses, Diego
García-Camacho, Aimara
Vicent-Morales, Maria
Benet-Buchholz, Jordi
Funes-Ardoiz, Ignacio
Kleij, Arjan W.
author Tóth, Balázs L.
author_facet Tóth, Balázs L.
Delgado, Alejandro
Ghorai, Debasish
Meneses, Diego
García-Camacho, Aimara
Vicent-Morales, Maria
Benet-Buchholz, Jordi
Funes-Ardoiz, Ignacio
Kleij, Arjan W.
author_role author
author2 Delgado, Alejandro
Ghorai, Debasish
Meneses, Diego
García-Camacho, Aimara
Vicent-Morales, Maria
Benet-Buchholz, Jordi
Funes-Ardoiz, Ignacio
Kleij, Arjan W.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Química
54
topic Química
54
description A dual Co/photoredox catalytic coupling of 1,3-enynes and α,ß-unsaturated aliphatic aldehydes and ketones has been developed that creates access to highly functional 1,3-diene synthons through a regio- and stereoselective carbon-carbon coupling process. The scope of the process features diverse functionalized scaffolds with a high degree of molecular complexity. The synthetic utility of these 1,3-dienes is demonstrated including a telescoped, one-pot approach using an alkynyl cyclic carbonate as a 1,3-enyne surrogate offering direct access to the 1,3-diene product. Mechanistic analysis involving control reactions, deuterium labeling studies and DFT calculations are in line with the in situ formation of a Co─H species and an outer-sphere coupling pathway in which a regio- and stereoselective coupling occurs between a dienyl radical and carbonyl species.
publishDate 2025
dc.date.none.fl_str_mv 2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/489064
https://doi.org/10.1002/anie.202522561
url http://hdl.handle.net/2072/489064
https://doi.org/10.1002/anie.202522561
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv CERCA Program/Generalitat de Catalunya
ICREA Foundation
MICIU/AEI (PID2023-149295NB-I00, RED2022-134074-T and Severo Ochoa Excellence Accreditation CEX2024-001469-S)
AGAUR (2021-SGR-00853)
B.L.T. acknowledges support from the European Union's Horizon 2020 research and innovation program under the Marie Skłodowska-Curie grant agreement 101026029
A.D. thanks MICINN for a predoctoral fellowship (PRE2021-100384)
A.G.-C and I.F.A thank MICIU/AEI/ 10.13039/501100011033 and Feder/EU for funding of the projects PID2021-126075NB-I00 and MICIU/AEI/10.13039/501100011033, and FSE + for a Ramón y Cajal fellowship (RYC2022–035776-I)
A.G-C. thanks the University of La Rioja and La Rioja Government for a predoctoral fellowship within the 2025 call.
dc.rights.none.fl_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/embargoedAccess
rights_invalid_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv 13 p.
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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 15.812429

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