Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media

Commercially available Quadrol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine (THPEN), has been used for the first time as N^N- donor neutral hydrophilic ligand in the synthesis and characterization of new water soluble palladium (II) complexes containing chloride, phthalimidate or sa...

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Autores: Serrano Martínez, José Luis, Gaware, Sujeet, Pérez López, José Antonio, Pérez Pérez, José, Lozano Rodríguez, Pedro, Kori, Santosh, Dandela, Rambabu, Sanghvi, Yogesh, Kapdi, Anant
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2022
País:España
Institución:Universidad Politécnica de Cartagena(UPCT)
Repositorio:Repositorio Digital UPCT
OAI Identifier:oai:repositorio.upct.es:10317/12899
Acceso en línea:http://hdl.handle.net/10317/12899
https://pubs.rsc.org/en/content/articlelanding/2022/dt/d1dt03778a/unauth
Access Level:acceso abierto
Palabra clave:Compuestos solubles
Mecánica de fluidos
Nucleósis en agua
Mecánica de Fluidos
2204.04 Mecánica de Fluidos
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spelling Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous mediaSerrano Martínez, José LuisGaware, SujeetPérez López, José AntonioPérez Pérez, JoséLozano Rodríguez, PedroKori, SantoshDandela, RambabuSanghvi, YogeshKapdi, AnantCompuestos solublesMecánica de fluidosNucleósis en aguaMecánica de Fluidos2204.04 Mecánica de FluidosCommercially available Quadrol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine (THPEN), has been used for the first time as N^N- donor neutral hydrophilic ligand in the synthesis and characterization of new water soluble palladium (II) complexes containing chloride, phthalimidate or saccharinate as co-ligands. [PdCl2(THPEN)] (1) [Pd(phthal)2(THPEN)] (2), [Pd(sacc)2(THPEN)] (3) and the analogous complex with the closely related N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine (THEEN) [Pd(sacc)2(THEEN)] (4) were efficiently prepared in a one-pot reaction from [PdCl2(CH3CN)2] or Pd(OAc)2. Structural characterization of 1 and 3 by single crystal X-ray diffraction produced the first structures reported to date of palladium complexes with Quadrol. The resultant palladium complexes are highly soluble in water and were found to be effective as phosphine-free catalysts for the synthesis of functionalized nucleoside analogues under room-temperature Suzuki-Miyaura cross-coupling conditions between 5-iodo-2'-deoxyuridine (& 5-iodo-2'-deoxycytidine) with different aryl boronic acids in neat water. This is the first report of the coupling process performed on nucleosides in water at room temperature.This work has been partially supported by RTI2018-098233-B-C21 (MICINN) and 20790/PI/18 (Fundación SENECA CARM) grants. A.R.K would like to acknowledge SERB for EMR grant (EMR/2016/005439). Professor Gregorio Sánchez, who recently passed away, is gratefully acknowledged for his contribution to this work and his wise and continuous advice and support.Royal Society of ChemistryMinisterio de Ciencia e InnovaciónFundación SénecaExtramural Research (EMR)202320232022info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfapplication/pdfhttp://hdl.handle.net/10317/12899https://pubs.rsc.org/en/content/articlelanding/2022/dt/d1dt03778a/unauthreponame:Repositorio Digital UPCTinstname:Universidad Politécnica de Cartagena(UPCT)InglésRTI2018-098233-B-C2120790/PI/18EMR/2016/005439info:eu-repo/semantics/openAccessoai:repositorio.upct.es:10317/128992026-05-15T06:39:02Z
dc.title.none.fl_str_mv Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
title Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
spellingShingle Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
Serrano Martínez, José Luis
Compuestos solubles
Mecánica de fluidos
Nucleósis en agua
Mecánica de Fluidos
2204.04 Mecánica de Fluidos
title_short Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
title_full Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
title_fullStr Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
title_full_unstemmed Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
title_sort Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
dc.creator.none.fl_str_mv Serrano Martínez, José Luis
Gaware, Sujeet
Pérez López, José Antonio
Pérez Pérez, José
Lozano Rodríguez, Pedro
Kori, Santosh
Dandela, Rambabu
Sanghvi, Yogesh
Kapdi, Anant
author Serrano Martínez, José Luis
author_facet Serrano Martínez, José Luis
Gaware, Sujeet
Pérez López, José Antonio
Pérez Pérez, José
Lozano Rodríguez, Pedro
Kori, Santosh
Dandela, Rambabu
Sanghvi, Yogesh
Kapdi, Anant
author_role author
author2 Gaware, Sujeet
Pérez López, José Antonio
Pérez Pérez, José
Lozano Rodríguez, Pedro
Kori, Santosh
Dandela, Rambabu
Sanghvi, Yogesh
Kapdi, Anant
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación
Fundación Séneca
Extramural Research (EMR)
dc.subject.none.fl_str_mv Compuestos solubles
Mecánica de fluidos
Nucleósis en agua
Mecánica de Fluidos
2204.04 Mecánica de Fluidos
topic Compuestos solubles
Mecánica de fluidos
Nucleósis en agua
Mecánica de Fluidos
2204.04 Mecánica de Fluidos
description Commercially available Quadrol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine (THPEN), has been used for the first time as N^N- donor neutral hydrophilic ligand in the synthesis and characterization of new water soluble palladium (II) complexes containing chloride, phthalimidate or saccharinate as co-ligands. [PdCl2(THPEN)] (1) [Pd(phthal)2(THPEN)] (2), [Pd(sacc)2(THPEN)] (3) and the analogous complex with the closely related N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine (THEEN) [Pd(sacc)2(THEEN)] (4) were efficiently prepared in a one-pot reaction from [PdCl2(CH3CN)2] or Pd(OAc)2. Structural characterization of 1 and 3 by single crystal X-ray diffraction produced the first structures reported to date of palladium complexes with Quadrol. The resultant palladium complexes are highly soluble in water and were found to be effective as phosphine-free catalysts for the synthesis of functionalized nucleoside analogues under room-temperature Suzuki-Miyaura cross-coupling conditions between 5-iodo-2'-deoxyuridine (& 5-iodo-2'-deoxycytidine) with different aryl boronic acids in neat water. This is the first report of the coupling process performed on nucleosides in water at room temperature.
publishDate 2022
dc.date.none.fl_str_mv 2022
2023
2023
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/10317/12899
https://pubs.rsc.org/en/content/articlelanding/2022/dt/d1dt03778a/unauth
url http://hdl.handle.net/10317/12899
https://pubs.rsc.org/en/content/articlelanding/2022/dt/d1dt03778a/unauth
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv RTI2018-098233-B-C21
20790/PI/18
EMR/2016/005439
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:Repositorio Digital UPCT
instname:Universidad Politécnica de Cartagena(UPCT)
instname_str Universidad Politécnica de Cartagena(UPCT)
reponame_str Repositorio Digital UPCT
collection Repositorio Digital UPCT
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300724

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