Selective synthesis and reactivity of eta(5)-arylcyclohexadienyliron complexes

David A. Owen, Andrei V. Malkov, Ian M. Palotai, Caroline Roe, Elizabeth J. Sandoe, G. Richard Stephenson

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17 Citations (Scopus)


A series of aryl-substituted cyclohexadienyliron complexes have been prepared by a general procedure that determines regioselectivity by correctly positioning leaving groups in the precursor complexes. The aryl groups at 1-C or 2-C have been shown to be omega directing by the study of reactions with a representative range of nucleophiles, and these regioselectivity properties have been related to the spectroscopic properties of the cationic cyclohexadienyliron complexes. A high level of electron-donating substituents on the arene, or switching between the [Fe(CO)(3)] and [Fe(CO)(2)PPh3] series, reduces the minor ipso pathway, improving regiocontrol. Placing opposed directing groups in the arylcyclohexadienyliron complexes reverts reactivity to the ipso pathway with stabilised enolate nucleophiles, and when the additional directing group reinforces the effect of the aryl group, the ipso pathway is stopped.
Original languageEnglish
Pages (from-to)4293-4311
Number of pages19
JournalChemistry - A European Journal
Issue number15
Publication statusPublished - 2007

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