Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
The synthesis and characterization of new water-soluble dinuclear palladacycles of the general formula [{Pd(R-C^N-SO3Na)(μ-AcO)}2] (R = H (1), OMe (2), Cl (3)) incorporating an ortho-metalated sodium 4-(N-benzylideneamino)benzenesulfonate moiety is reported. These complexes have been revealed to be...
| Autores: | , , , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2020 |
| País: | España |
| Institución: | Universidad Politécnica de Cartagena(UPCT) |
| Repositorio: | Repositorio Digital UPCT |
| OAI Identifier: | oai:repositorio.upct.es:10317/12880 |
| Acceso en línea: | http://hdl.handle.net/10317/12880 https://pubs.acs.org/doi/10.1021/acs.organomet.0c00580 |
| Access Level: | acceso abierto |
| Palabra clave: | Catalysts Ligands Nucleic acids Palladium Solvents Química Inorgánica 2303 Química Inorgánica |
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Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous mediaSerrano Martínez, José LuisGarcía González, LuisPérez Pérez, JoséLozano, PedroCorreia, JevyKori, SantoshKapdi, Anant R.Sanghvi, Yogesh S.CatalystsLigandsNucleic acidsPalladiumSolventsQuímica Inorgánica2303 Química InorgánicaThe synthesis and characterization of new water-soluble dinuclear palladacycles of the general formula [{Pd(R-C^N-SO3Na)(μ-AcO)}2] (R = H (1), OMe (2), Cl (3)) incorporating an ortho-metalated sodium 4-(N-benzylideneamino)benzenesulfonate moiety is reported. These complexes have been revealed to be excellent phosphine-free catalysts for the synthesis of functionalized nucleoside analogues involving a low-temperature Suzuki–Miyaura coupling of 5-iodo-2′-deoxyuridine with different arylboronic acids in neat water. The potential of 1–3 as synthetic precursors was also tested, and bridging acetates were cleaved by reaction with neutral PPh3, yielding the corresponding mononuclear derivatives [Pd(R-C^N-SO3Na)(AcO)(PPh3)] (R = H (4), MeO (5), Cl (6)). Analytical and spectroscopic techniques confirmed the proposed formulas and reactivities reported for complexes 1–6. Structural characterization by X-ray diffraction of single crystals grown from samples of 4 and 6 produced the unexpected but valuable crystallization-mediated compounds 4cm and 6cm that also supported the results presented here.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 advise and supportAmerical Chemical Society (ACS)Ministerio de Ciencia e InnovaciónFundación SénecaExtramural Research (EMR)202320232020info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfapplication/pdfhttp://hdl.handle.net/10317/12880https://pubs.acs.org/doi/10.1021/acs.organomet.0c00580reponame:Repositorio Digital UPCTinstname:Universidad Politécnica de Cartagena(UPCT)Ingléshttps://pubs.acs.org/doi/abs/10.1021/acs.organomet.0c00580RTI2018-098233-B-C2120790/PI/18EMR/2016/005439info:eu-repo/semantics/openAccessoai:repositorio.upct.es:10317/128802026-05-15T06:39:02Z |
| dc.title.none.fl_str_mv |
Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media |
| title |
Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media |
| spellingShingle |
Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media Serrano Martínez, José Luis Catalysts Ligands Nucleic acids Palladium Solvents Química Inorgánica 2303 Química Inorgánica |
| title_short |
Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media |
| title_full |
Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media |
| title_fullStr |
Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media |
| title_full_unstemmed |
Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media |
| title_sort |
Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media |
| dc.creator.none.fl_str_mv |
Serrano Martínez, José Luis García González, Luis Pérez Pérez, José Lozano, Pedro Correia, Jevy Kori, Santosh Kapdi, Anant R. Sanghvi, Yogesh S. |
| author |
Serrano Martínez, José Luis |
| author_facet |
Serrano Martínez, José Luis García González, Luis Pérez Pérez, José Lozano, Pedro Correia, Jevy Kori, Santosh Kapdi, Anant R. Sanghvi, Yogesh S. |
| author_role |
author |
| author2 |
García González, Luis Pérez Pérez, José Lozano, Pedro Correia, Jevy Kori, Santosh Kapdi, Anant R. Sanghvi, Yogesh S. |
| author2_role |
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 |
Catalysts Ligands Nucleic acids Palladium Solvents Química Inorgánica 2303 Química Inorgánica |
| topic |
Catalysts Ligands Nucleic acids Palladium Solvents Química Inorgánica 2303 Química Inorgánica |
| description |
The synthesis and characterization of new water-soluble dinuclear palladacycles of the general formula [{Pd(R-C^N-SO3Na)(μ-AcO)}2] (R = H (1), OMe (2), Cl (3)) incorporating an ortho-metalated sodium 4-(N-benzylideneamino)benzenesulfonate moiety is reported. These complexes have been revealed to be excellent phosphine-free catalysts for the synthesis of functionalized nucleoside analogues involving a low-temperature Suzuki–Miyaura coupling of 5-iodo-2′-deoxyuridine with different arylboronic acids in neat water. The potential of 1–3 as synthetic precursors was also tested, and bridging acetates were cleaved by reaction with neutral PPh3, yielding the corresponding mononuclear derivatives [Pd(R-C^N-SO3Na)(AcO)(PPh3)] (R = H (4), MeO (5), Cl (6)). Analytical and spectroscopic techniques confirmed the proposed formulas and reactivities reported for complexes 1–6. Structural characterization by X-ray diffraction of single crystals grown from samples of 4 and 6 produced the unexpected but valuable crystallization-mediated compounds 4cm and 6cm that also supported the results presented here. |
| publishDate |
2020 |
| dc.date.none.fl_str_mv |
2020 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/10317/12880 https://pubs.acs.org/doi/10.1021/acs.organomet.0c00580 |
| url |
http://hdl.handle.net/10317/12880 https://pubs.acs.org/doi/10.1021/acs.organomet.0c00580 |
| dc.language.none.fl_str_mv |
Inglés |
| language_invalid_str_mv |
Inglés |
| dc.relation.none.fl_str_mv |
https://pubs.acs.org/doi/abs/10.1021/acs.organomet.0c00580 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 |
Americal Chemical Society (ACS) |
| publisher.none.fl_str_mv |
Americal Chemical Society (ACS) |
| dc.source.none.fl_str_mv |
reponame:Repositorio Digital UPCT instname:Universidad Politécnica de Cartagena(UPCT) |
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Universidad Politécnica de Cartagena(UPCT) |
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Repositorio Digital UPCT |
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Repositorio Digital UPCT |
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| repository.mail.fl_str_mv |
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1869423129856573441 |
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15,300724 |