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 language | English (US) |
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Pages (from-to) | 1934-1937 |
Number of pages | 4 |
Journal | Journal of Organometallic Chemistry |
Volume | 694 |
Issue number | 12 |
DOIs | |
State | Published - May 15 2009 |
Externally published | Yes |
Bibliographical note
Funding Information:We thank the Stifterverband für die Deutsche Wissenschaft (project 11047), the Elitenetzwerk Bayern e.V. (graduate fellowships for T.R. and A.N.M.) and the IDK NanoCat for generous financial support.
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