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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]
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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]
ISSN:00201693
DOI:10.1016/j.ica.2022.121062