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Issue 21, 2003
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Room-temperature cyclometallation of amines, imines and oxazolines with [MCl2Cp*]2(M = Rh, Ir) and [RuCl2(p-cymene)]2

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Abstract

N,N-Dimethylbenzylamine, alkyl and aryl imines derived from benzaldehyde, and 2-phenyl-4,4-dimethyloxazoline all undergo cyclometallation with [IrCl2Cp*]2 (Cp* = η-C5Me5) when treated with NaOAc in dichloromethane at room temperature. The imines are also cyclometallated by [RhCl2Cp*]2 under the same conditions whilst only N-alkyl imines are cyclometallated by [RuCl2(p-cymene)]2. The role of acetate in the cyclometallation is more than just as a base. X-Ray structures of cyclometallated complexes [MCl{C6H4-2-C(H)[double bond, length as m-dash]NCH2CH2OMe-κC,N}(η-ring)](M = Ir, Rh ring = Cp*; M = Ru, ring = p-cymene), [MCl{C6H4-2-C(H)[double bond, length as m-dash]NCH2CH2OMe-κC,N}Cp*](M = Ir, Rh), [RuCl(η2-O2CMe)(p-cymene)] and [IrCl2(NH2Ph)Cp*] are reported.

Graphical abstract: Room-temperature cyclometallation of amines, imines and oxazolines with [MCl2Cp*]2 (M = Rh, Ir) and [RuCl2(p-cymene)]2

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Publication details

The article was received on 03 Apr 2003, accepted on 03 Jun 2003 and first published on 22 Sep 2003


Article type: Paper
DOI: 10.1039/B303737A
Citation: Dalton Trans., 2003, 4132-4138
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    Room-temperature cyclometallation of amines, imines and oxazolines with [MCl2Cp*]2 (M = Rh, Ir) and [RuCl2(p-cymene)]2

    D. L. Davies, O. Al-Duaij, J. Fawcett, M. Giardiello, S. T. Hilton and D. R. Russell, Dalton Trans., 2003, 4132
    DOI: 10.1039/B303737A

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