C–S couplings catalyzed by Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)].
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| Title: | C–S couplings catalyzed by Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)]. |
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| Authors: | Jaimes–Romano, Eduardo1 (AUTHOR), Valdés, Hugo1,2 (AUTHOR) hugo.valdes@udg.edu, Hernández–Ortega, Simon1 (AUTHOR), Mollfulleda, Rosa2 (AUTHOR), Swart, Marcel1,3 (AUTHOR) marcel.swart@udg.edu, Morales–Morales, David1 (AUTHOR) damor@unam.mx |
| Source: | Journal of Catalysis. Oct2023, Vol. 426, p247-256. 10p. |
| Subjects: | Catalytic activity, Nickel catalysts, Ligands (Chemistry), Iodobenzene, Thiophenol |
| Abstract: | [Display omitted] • Two fluorinated and one non–fluorinated complex of the type [(NHC)Ni(Cp)(Br)] were synthesized and characterized. • The non–fluorinated complex showed higher catalytic activity than the fluorinated ones in the C–S cross–coupling reaction. • The catalytic reaction mechanism was studied by theoretical calculations. • Strong nucleophilic substrates quenched the C–S cross–coupling by forming a stable intermediate complex. 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%). [ABSTRACT FROM AUTHOR] |
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| Database: | Engineering Source |
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