Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction

Homogeneous transition metal catalysis is a constantly developing field in chemical sciences. A growing interest in this area is photoswitchable catalysis, which pursues in situ modulation of catalyst activity through noninvasive light irradiation. Phosphorus ligands are excellent targets to accompl...

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Autores: Sherstiuk, Anastasiia|||0000-0002-4628-6433, Lledós, Agustí|||0000-0001-7909-422X, Lönnecke, Peter|||0000-0003-1335-0897, Hernando, Jordi|||0000-0002-1126-4138, Sebastián, Rosa María|||0000-0001-5519-9131, Hey-Hawkins, Evamarie|||0000-0003-4267-0603
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:291322
Acceso en línea:https://ddd.uab.cat/record/291322
https://dx.doi.org/urn:doi:10.1021/acs.inorgchem.3c04423
Access Level:acceso abierto
Palabra clave:Dithienylethenes
Phosphines
Catalysis
Photoswitch
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spelling Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reactionSherstiuk, Anastasiia|||0000-0002-4628-6433Lledós, Agustí|||0000-0001-7909-422XLönnecke, Peter|||0000-0003-1335-0897Hernando, Jordi|||0000-0002-1126-4138Sebastián, Rosa María|||0000-0001-5519-9131Hey-Hawkins, Evamarie|||0000-0003-4267-0603DithienylethenesPhosphinesCatalysisPhotoswitchHomogeneous transition metal catalysis is a constantly developing field in chemical sciences. A growing interest in this area is photoswitchable catalysis, which pursues in situ modulation of catalyst activity through noninvasive light irradiation. Phosphorus ligands are excellent targets to accomplish this goal by introducing photoswitchable moieties; however, only a limited number of examples have been reported so far. In this work, we have developed a series of palladium complexes capable of catalyzing the Stille coupling reaction that contain photoisomerizable phosphine ligands based on dithienylethene switches. Incorporation of electron-withdrawing substituents into these dithienylethene moieties allows variation of the electron density on the phosphorus atom of the ligands upon light irradiation, which in turn leads to a modulation of the catalytic properties of the formed complexes and their activity in a model Stille coupling reaction. These results are supported by theoretical computations, which show that the energy barriers for the rate-determining steps of the catalytic cycle decrease when the photoswitchable phosphine ligands are converted to their closed state. 22024-01-0120242024-01-01Articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://ddd.uab.cat/record/291322https://dx.doi.org/urn:doi:10.1021/acs.inorgchem.3c04423reponame:Dipòsit Digital de Documents de la UABinstname:Universitat Autònoma de BarcelonaInglésengEuropean Commission https://doi.org/10.13039/501100000780 860322Agència de Gestió d'Ajuts Universitaris i de Recerca https://doi.org/10.13039/501100003030 2021/SGR-00064open accesshttp://purl.org/coar/access_right/c_abf2Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, la comunicació pública de l'obra i la creació d'obres derivades, fins i tot amb finalitats comercials, sempre i quan es reconegui l'autoria de l'obra original.https://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:ddd.uab.cat:2913222026-06-06T12:50:31Z
dc.title.none.fl_str_mv Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction
title Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction
spellingShingle Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction
Sherstiuk, Anastasiia|||0000-0002-4628-6433
Dithienylethenes
Phosphines
Catalysis
Photoswitch
title_short Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction
title_full Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction
title_fullStr Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction
title_full_unstemmed Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction
title_sort Dithienylethene-based photoswitchable phosphines for palladium-catalyzed Stille coupling reaction
dc.creator.none.fl_str_mv Sherstiuk, Anastasiia|||0000-0002-4628-6433
Lledós, Agustí|||0000-0001-7909-422X
Lönnecke, Peter|||0000-0003-1335-0897
Hernando, Jordi|||0000-0002-1126-4138
Sebastián, Rosa María|||0000-0001-5519-9131
Hey-Hawkins, Evamarie|||0000-0003-4267-0603
author Sherstiuk, Anastasiia|||0000-0002-4628-6433
author_facet Sherstiuk, Anastasiia|||0000-0002-4628-6433
Lledós, Agustí|||0000-0001-7909-422X
Lönnecke, Peter|||0000-0003-1335-0897
Hernando, Jordi|||0000-0002-1126-4138
Sebastián, Rosa María|||0000-0001-5519-9131
Hey-Hawkins, Evamarie|||0000-0003-4267-0603
author_role author
author2 Lledós, Agustí|||0000-0001-7909-422X
Lönnecke, Peter|||0000-0003-1335-0897
Hernando, Jordi|||0000-0002-1126-4138
Sebastián, Rosa María|||0000-0001-5519-9131
Hey-Hawkins, Evamarie|||0000-0003-4267-0603
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Dithienylethenes
Phosphines
Catalysis
Photoswitch
topic Dithienylethenes
Phosphines
Catalysis
Photoswitch
description Homogeneous transition metal catalysis is a constantly developing field in chemical sciences. A growing interest in this area is photoswitchable catalysis, which pursues in situ modulation of catalyst activity through noninvasive light irradiation. Phosphorus ligands are excellent targets to accomplish this goal by introducing photoswitchable moieties; however, only a limited number of examples have been reported so far. In this work, we have developed a series of palladium complexes capable of catalyzing the Stille coupling reaction that contain photoisomerizable phosphine ligands based on dithienylethene switches. Incorporation of electron-withdrawing substituents into these dithienylethene moieties allows variation of the electron density on the phosphorus atom of the ligands upon light irradiation, which in turn leads to a modulation of the catalytic properties of the formed complexes and their activity in a model Stille coupling reaction. These results are supported by theoretical computations, which show that the energy barriers for the rate-determining steps of the catalytic cycle decrease when the photoswitchable phosphine ligands are converted to their closed state.
publishDate 2024
dc.date.none.fl_str_mv 2
2024-01-01
2024
2024-01-01
dc.type.none.fl_str_mv Article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://ddd.uab.cat/record/291322
https://dx.doi.org/urn:doi:10.1021/acs.inorgchem.3c04423
url https://ddd.uab.cat/record/291322
https://dx.doi.org/urn:doi:10.1021/acs.inorgchem.3c04423
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv European Commission https://doi.org/10.13039/501100000780 860322
Agència de Gestió d'Ajuts Universitaris i de Recerca https://doi.org/10.13039/501100003030 2021/SGR-00064
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Dipòsit Digital de Documents de la UAB
instname:Universitat Autònoma de Barcelona
instname_str Universitat Autònoma de Barcelona
reponame_str Dipòsit Digital de Documents de la UAB
collection Dipòsit Digital de Documents de la UAB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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