C–S couplings catalyzed by Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)]
dc.contributor.author
dc.date.accessioned
2023-10-25T10:31:13Z
dc.date.available
2023-10-25T10:31:13Z
dc.date.issued
2023-10
dc.identifier.issn
0021-9517
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dc.description.abstract
The catalytic activities of three Ni(II) complexes with fluorinated and non–fluorinated N–heterocyclic carbene (NHC) ligands were evaluated in the C–S cross–coupling reaction between iodobenzene and thiophenol. The complexes with fluorinated–NHC ligands exhibited lower catalytic activities compared to the non–fluorinated derivative. This can be attributed to the lower electron–donating character of the fluorinated ligands in comparison to the non–fluorinated ligand. Complex 3–Ni was tested towards different substrates, achieving moderate to good conversions. Additionally, the reaction mechanism of the C–S cross–coupling using two substrates, tert–butylthiol and 2,4–dichlorobenzenethiol, was determined. Tert–butylthiol produced a stable intermediate that inhibited the last step of the reaction mechanism (reductive elimination). On the other hand, 2,4–dichlorobenzenethiol formed a less stable intermediate, favoring the reductive elimination. This observation aligns with the lower yield observed when using tert–butylthiol compared to 2,4–dichlorobenzenethiol (20% vs 99%)
dc.description.sponsorship
We would like to thank Dr. Francisco Javier Pérez Flores, Q. Eréndira García Ríos, M.Sc. Lucia del Carmen Márquez Alonso, M.Sc. Lucero Ríos Ruíz, M.Sc. Alejandra Núñez Pineda (CCIQS), Q. María de la Paz Orta Pérez, Q. Roció Patiño–Maya and Ph.D. Nuria Esturau Escofet for technical assistance. E. J.-R. thanks Programa de Becas CONACyT (Número de becario: 837819). Hugo Valdés thanks the Generalitat de Catalunya for a Beatriu de Pinós contract (grant ID: 2019–BP–0080). The financial support of this research by PAPIIT–DGAPA–UNAM (PAPIIT IN223323), CONACYT A1–S–033933, AEI/MCIU (PID2020–114548 GB–I00, PRE2021–097669), the Generalitat de Catalunya (2021SGR00487), and FEDER (UNGI10–4E–801) is gratefully acknowledged.
Open Access funding provided thanks to the CRUE-CSIC agreement with Elsevier
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application/pdf
dc.language.iso
eng
dc.publisher
Elsevier
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Reproducció digital del document publicat a: https://doi.org/10.1016/j.jcat.2023.07.001
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Journal of Catalysis, 2023, vol. 426, p. 247-256
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Articles publicats (D-Q)
dc.rights
Attribution-NonCommercial-NoDerivatives 4.0 International
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dc.subject
dc.title
C–S couplings catalyzed by Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)]
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.type.peerreviewed
peer-reviewed
dc.identifier.eissn
1090-2694