Oxidative addition reactions of alkyl halides with the group 13 carbene analogue [In{N(Dipp)C(Me)}2CH] (Dipp = 2,6-iPr 2C6H3)

Michael S. Hill, Peter B. Hitchcock, Ruti Pongtavornpinyo

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Reactions of the well-defined two-coordinate indium "carbene analogue" [In{N(Dipp)-C(Me)}2CH] (Dipp = 2,6-iPr 2C6H3) have been studied. Reactions of Mel, iPrl, and tBul with [In{N(Dipp)C(Me)}2CH] formed by the in situ reaction of InI, [K{N(SiMe3)2}], and the iminoenamine ligand precursor successfully yielded the oxidative addition products [InRI{N(Dipp)C(Me)}2CH] (R = Me, iPr, tBu). The results of NMR investigations, which indicated the formation of a series of four-coordinate indium(III) complexes in C 6D6 solution, were confirmed in the solid-state by single-crystal X-ray diffraction. Similar reactions employing alkyl bromides were unsuccessful and resulted in the isolation of the corresponding iodides, apparently by metathesis of the bromide oxidative addition product with Kl formed during the initial InI metathesis. Reactions of isolated samples of [In{N(Dipp)C(Me)}2CH] with iPrBr and tBuBr, however, were straightforward and resulted in the successful isolation of the analogous iso-propyl and tert-butyl indium(III) bromide complexes. These were also fully characterized by 1H and 13C NMR and single-crystal X-ray diffraction experiments. In contrast, no reaction was observed between [In{N(Dipp)-C(Me)}2CH] and aryl halides or alkyl chlorides.

Original languageEnglish
Pages (from-to)3783-3788
Number of pages6
JournalInorganic Chemistry
Issue number9
Publication statusPublished - 30 Apr 2007

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry


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