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Issue 32, 2013
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Half-sandwich rhodium and iridium complexes containing homochiral imidazolyl-imine ligands: synthesis, characterization and catalytic applications

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Abstract

Condensation of homochiral primary amines with 1-methyl-1H-imidazole-2-carbaldehyde affords the corresponding imidazolyl-imine compounds (L11–L33) which have been employed as ligands for the preparation of half-sandwich rhodium and iridium complexes of the formula [(η5-C5Me5)MClLnnn][SbF6]. Treatment of these chloride compounds with AgSbF6 renders dicationic aqua-complexes [(η5-C5Me5)MLnnn(H2O)] [SbF6]2 which act as catalysts for the Diels–Alder reaction between methacrolein and cyclopentadiene. Catalysis occurs with good exo : endo selectivity and poor enantioselectivity. All the compounds have been completely characterized by analytical and spectroscopic methods. Characterization includes the molecular structure determination of the complexes [(η5-C5Me5)MClLnnn][SbF6] (Lnnn = L11111, M = Rh, (1) Ir (4); Lnnn = L3333, M = Ir (6)) and [(η5-C5Me5)ML11111(H2O)][SbF6]2 (M = Rh (7), Ir (10)) using X-ray diffraction. From the stereochemical properties of the organometallic precursors the catalytic outcome is discussed.

Graphical abstract: Half-sandwich rhodium and iridium complexes containing homochiral imidazolyl-imine ligands: synthesis, characterization and catalytic applications

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Publication details

The article was received on 09 May 2013, accepted on 22 Jun 2013 and first published on 24 Jun 2013


Article type: Paper
DOI: 10.1039/C3DT51222C
Citation: Dalton Trans., 2013,42, 11640-11651
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    Half-sandwich rhodium and iridium complexes containing homochiral imidazolyl-imine ligands: synthesis, characterization and catalytic applications

    A. Becerra, R. Contreras, D. Carmona, F. J. Lahoz and P. García-Orduña, Dalton Trans., 2013, 42, 11640
    DOI: 10.1039/C3DT51222C

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