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Addition of aliphatic, secondary amines to coordinated isonitriles. N-acyclic carbene (NAC) platinum(II) complexes from trans-[Pt(μ-Cl)Cl(PPh3)]2.

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Title: Addition of aliphatic, secondary amines to coordinated isonitriles. N-acyclic carbene (NAC) platinum(II) complexes from trans-[Pt(μ-Cl)Cl(PPh3)]2.
Authors: Farasat, Anna1 (AUTHOR), Labella, Luca1 (AUTHOR), Marchetti, Fabio1 (AUTHOR), Samaritani, Simona1 (AUTHOR) simona.samaritani@unipi.it
Source: Inorganica Chimica Acta. Sep2022, Vol. 540, pN.PAG-N.PAG. 1p.
Subjects: Secondary amines, Isocyanides, Platinum, Nucleophilic reactions, Pyrrolidine
Abstract: [Display omitted] • Isonitriles RNC react with trans -[Pt(μ-Cl)Cl(PPh 3)] 2 giving cis -[PtCl 2 (PPh 3)(CNR)]. • cis -[PtCl 2 (PPh 3)(CNR)] add acyclic N, N -dialkylamines affording cis- carbenes. • Substitution of the chlorido ion trans to carbene is observed with cyclic amines. • Both isonitrile- and carbene Pt(II) complexes prepared are stable in DMSO. • The sequence can afford libraries of potentially antiproliferative compounds. Isocyanide ligands RNC (R = 4-(MeO)C 6 H 4 -, PhCH 2) react smoothly with trans- [Pt(μ-Cl)Cl(PPh 3)] 2 to afford trans- [PtCl 2 (PPh 3)(CNR)] complexes, which are promptly converted, in solution, to the corresponding cis isomers. The obtained derivatives react with N,N -dialkylamines to afford the corresponding N -acyclic carbene (NAC) addition products. When alicyclic N,N -dialkylamine (Ŕ 2 NH, Ŕ= ethyl, benzyl) were used, only the expected neutral dichlorocarbene product cis- [PtCl 2 (PPh 3)(Ŕ 2 NCN(H)R)] were obtained in high yields, while when cyclic amines R ′ 2 N ^ H were used (morpholine, piperidine, pyrrolidine), variable amounts of ionic [PtCl(PPh 3)( R ′ 2 N ^ H)(R ′ 2 N ^ CN(H)R)]Cl were observed, arising from the substitution of a residual chlorido ligand by the used amine. The amount of the ionic derivative observed depends on the amine nucleophilicity. [ABSTRACT FROM AUTHOR]
Copyright of Inorganica Chimica Acta is the property of Elsevier B.V. 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.)
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Items – Name: Title
  Label: Title
  Group: Ti
  Data: Addition of aliphatic, secondary amines to coordinated isonitriles. N-acyclic carbene (NAC) platinum(II) complexes from trans-[Pt(μ-Cl)Cl(PPh3)]2.
– Name: Author
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  Data: <searchLink fieldCode="AR" term="%22Farasat%2C+Anna%22">Farasat, Anna</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Labella%2C+Luca%22">Labella, Luca</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Marchetti%2C+Fabio%22">Marchetti, Fabio</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Samaritani%2C+Simona%22">Samaritani, Simona</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> simona.samaritani@unipi.it</i>
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  Data: <searchLink fieldCode="JN" term="%22Inorganica+Chimica+Acta%22">Inorganica Chimica Acta</searchLink>. Sep2022, Vol. 540, pN.PAG-N.PAG. 1p.
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  Label: Subjects
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  Data: <searchLink fieldCode="DE" term="%22Secondary+amines%22">Secondary amines</searchLink><br /><searchLink fieldCode="DE" term="%22Isocyanides%22">Isocyanides</searchLink><br /><searchLink fieldCode="DE" term="%22Platinum%22">Platinum</searchLink><br /><searchLink fieldCode="DE" term="%22Nucleophilic+reactions%22">Nucleophilic reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Pyrrolidine%22">Pyrrolidine</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: [Display omitted] • Isonitriles RNC react with trans -[Pt(μ-Cl)Cl(PPh 3)] 2 giving cis -[PtCl 2 (PPh 3)(CNR)]. • cis -[PtCl 2 (PPh 3)(CNR)] add acyclic N, N -dialkylamines affording cis- carbenes. • Substitution of the chlorido ion trans to carbene is observed with cyclic amines. • Both isonitrile- and carbene Pt(II) complexes prepared are stable in DMSO. • The sequence can afford libraries of potentially antiproliferative compounds. Isocyanide ligands RNC (R = 4-(MeO)C 6 H 4 -, PhCH 2) react smoothly with trans- [Pt(μ-Cl)Cl(PPh 3)] 2 to afford trans- [PtCl 2 (PPh 3)(CNR)] complexes, which are promptly converted, in solution, to the corresponding cis isomers. The obtained derivatives react with N,N -dialkylamines to afford the corresponding N -acyclic carbene (NAC) addition products. When alicyclic N,N -dialkylamine (Ŕ 2 NH, Ŕ= ethyl, benzyl) were used, only the expected neutral dichlorocarbene product cis- [PtCl 2 (PPh 3)(Ŕ 2 NCN(H)R)] were obtained in high yields, while when cyclic amines R ′ 2 N ^ H were used (morpholine, piperidine, pyrrolidine), variable amounts of ionic [PtCl(PPh 3)( R ′ 2 N ^ H)(R ′ 2 N ^ CN(H)R)]Cl were observed, arising from the substitution of a residual chlorido ligand by the used amine. The amount of the ionic derivative observed depends on the amine nucleophilicity. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Inorganica Chimica Acta is the property of Elsevier B.V. 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.)
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      – Type: doi
        Value: 10.1016/j.ica.2022.121062
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      – Code: eng
        Text: English
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        PageCount: 1
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    Subjects:
      – SubjectFull: Secondary amines
        Type: general
      – SubjectFull: Isocyanides
        Type: general
      – SubjectFull: Platinum
        Type: general
      – SubjectFull: Nucleophilic reactions
        Type: general
      – SubjectFull: Pyrrolidine
        Type: general
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      – TitleFull: Addition of aliphatic, secondary amines to coordinated isonitriles. N-acyclic carbene (NAC) platinum(II) complexes from trans-[Pt(μ-Cl)Cl(PPh3)]2.
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            NameFull: Farasat, Anna
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            NameFull: Labella, Luca
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            NameFull: Marchetti, Fabio
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            NameFull: Samaritani, Simona
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            – D: 24
              M: 09
              Text: Sep2022
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              Y: 2022
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              Value: 540
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