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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Highly trifluoromethylated platinum compounds.
Sonia Martínez-Salvador1, Juan Forniés, Antonio Martín
1Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-C.S.I.C. c/ Pedro Cerbuna 12, 50009 Zaragoza, Spain.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 8, 2011
Summary
This study introduces novel platinum(IV) compounds with high trifluoromethyl (CF3) content. These highly fluorinated organometallic compounds offer a new entry point into platinum chemistry.
Area of Science:
- Organometallic Chemistry
- Fluorine Chemistry
- Platinum Chemistry
Background:
- Homoleptic square-planar organoplatinum(II) compounds are precursors to more complex platinum species.
- Trifluoromethyl ligands significantly influence the properties of organometallic compounds.
Purpose of the Study:
- To synthesize and characterize novel, highly trifluoromethylated platinum(IV) complexes.
- To explore the reactivity of a key platinum(IV) intermediate with various ligands.
- To establish a convenient entry into the chemistry of highly trifluoromethylated platinum compounds.
Main Methods:
- Oxidative addition of trifluoromethyl iodide to a platinum(II) precursor.
- Ligand exchange reactions using silver(I) salts in different solvents (acetone, acetonitrile).
- Synthesis of new platinum(IV) complexes with various neutral and anionic ligands.
- X-ray diffraction analysis for structural determination of key compounds.
Main Results:
- Synthesis of a highly trifluoromethylated platinum(IV) complex, [NBu(4)](2)[Pt(CF(3))(5)I] (2), via oxidative addition.
- Formation of aquo ([NBu(4)][Pt(CF(3))(5)(OH2)]) and acetonitrile ([NBu(4)][Pt(CF(3))(5)(NCMe)]) complexes.
- Successful replacement of labile ligands to yield a series of pentakis(trifluoromethyl)platinate(IV) compounds with diverse ligands (CO, pyridine, tetrahydrothiophene, chloride, bromide).
- Isolation and characterization of organoelement compounds with the highest CF3 content to date.
Conclusions:
- The synthesized platinum(IV) complex (2) serves as a versatile precursor for highly trifluoromethylated platinum chemistry.
- The labile aquo and acetonitrile ligands facilitate the introduction of various functional groups onto the platinum center.
- This work expands the scope of known organometallic compounds with exceptionally high fluorine content.
