Side chain functionalized η5-tetramethyl cyclopentadienyl complexes of Rh and Ir with a pendant primary amine group

Thomas Reiner, Dominik Jantke, Andreas Raba, Alexander N. Marziale, Jorg Eppinger*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Conversion of 2-(2,3,4,5-tetramethylcyclopentadien)ethylamine tautomere C5Me4H2(CHCH2)NH2 (1) with MCl3 · n H2O (M = Rh, Ir) under acidic conditions gives the respective μ-chloro-bridged chelates [(η5-Me4Cp(CH2)2NH3)RhCl2]2Cl2 (2) and [(η5-Me4Cp(CH2)2NH3)IrCl2]2Cl2 (3). The dimeric complexes are received as ammonium salts and thus display good solubility in strong donor solvents such as water and DMSO. Addition of triphenyl phosphine converts Rh-dimer 2 into the mononuclear phosphine complex 4. Under basic conditions, no intramolecular coordination of the pendant NH2 is observed and thus the primary amino group of 4 reacts selectively with succinic anhydride by formation of a peptide bond. Hence, the electrophilic metal center and the latent nucleophilic nitrogen, which represent complementary functionalities, can be addressed separately under the appropriate reaction conditions.

Original languageEnglish (US)
Pages (from-to)1934-1937
Number of pages4
JournalJournal of Organometallic Chemistry
Volume694
Issue number12
DOIs
StatePublished - May 15 2009

Keywords

  • Cyclopentadiene derivative
  • Functionalized metal complexes
  • Iridium
  • Metal peptide conjugation
  • Rhodium

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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