View in EDS

C–S couplings catalyzed by Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)].

Saved in:
Bibliographic Details
Title: C–S couplings catalyzed by Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)].
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]
Copyright of Journal of Catalysis is the property of Academic Press Inc. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
FullText Text:
  Availability: 0
Header DbId: egs
DbLabel: Engineering Source
An: 170066497
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: C–S couplings catalyzed by Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)].
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AR" term="%22Jaimes–Romano%2C+Eduardo%22">Jaimes–Romano, Eduardo</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Valdés%2C+Hugo%22">Valdés, Hugo</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<i> hugo.valdes@udg.edu</i><br /><searchLink fieldCode="AR" term="%22Hernández–Ortega%2C+Simon%22">Hernández–Ortega, Simon</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Mollfulleda%2C+Rosa%22">Mollfulleda, Rosa</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Swart%2C+Marcel%22">Swart, Marcel</searchLink><relatesTo>1,3</relatesTo> (AUTHOR)<i> marcel.swart@udg.edu</i><br /><searchLink fieldCode="AR" term="%22Morales–Morales%2C+David%22">Morales–Morales, David</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> damor@unam.mx</i>
– Name: TitleSource
  Label: Source
  Group: Src
  Data: <searchLink fieldCode="JN" term="%22Journal+of+Catalysis%22">Journal of Catalysis</searchLink>. Oct2023, Vol. 426, p247-256. 10p.
– Name: Subject
  Label: Subjects
  Group: Su
  Data: <searchLink fieldCode="DE" term="%22Catalytic+activity%22">Catalytic activity</searchLink><br /><searchLink fieldCode="DE" term="%22Nickel+catalysts%22">Nickel catalysts</searchLink><br /><searchLink fieldCode="DE" term="%22Ligands+%28Chemistry%29%22">Ligands (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Iodobenzene%22">Iodobenzene</searchLink><br /><searchLink fieldCode="DE" term="%22Thiophenol%22">Thiophenol</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: [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]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Catalysis is the property of Academic Press Inc. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=egs&AN=170066497
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1016/j.jcat.2023.07.001
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 10
        StartPage: 247
    Subjects:
      – SubjectFull: Catalytic activity
        Type: general
      – SubjectFull: Nickel catalysts
        Type: general
      – SubjectFull: Ligands (Chemistry)
        Type: general
      – SubjectFull: Iodobenzene
        Type: general
      – SubjectFull: Thiophenol
        Type: general
    Titles:
      – TitleFull: C–S couplings catalyzed by Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)].
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Jaimes–Romano, Eduardo
      – PersonEntity:
          Name:
            NameFull: Valdés, Hugo
      – PersonEntity:
          Name:
            NameFull: Hernández–Ortega, Simon
      – PersonEntity:
          Name:
            NameFull: Mollfulleda, Rosa
      – PersonEntity:
          Name:
            NameFull: Swart, Marcel
      – PersonEntity:
          Name:
            NameFull: Morales–Morales, David
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 01
              M: 10
              Text: Oct2023
              Type: published
              Y: 2023
          Identifiers:
            – Type: issn-print
              Value: 00219517
          Numbering:
            – Type: volume
              Value: 426
          Titles:
            – TitleFull: Journal of Catalysis
              Type: main
ResultId 1