Heavier group-2-element catalyzed hydroamination of carbodiimides

Jennifer R. Lachs, Anthony G.M. Barrett, Mark R. Crimmin, Gabriele Kociok-Köhn, Michael S. Hill, Mary F. Mahon, Panayiotis A. Procopiou

Research output: Contribution to journalArticlepeer-review

70 Citations (Scopus)

Abstract

The heteroleptic calcium amide [{ArNC(Me)CHC(Me)-NAr}Ca{N(SiMe 3)2}(THF)] (Ar = 2,6-diisopropylphenyl) and the homoleptic heavier alkaline earth amides, [M{N(Si-Me3)2} 2(THF)2] (M = Ca, Sr and Ba) are reported as competent pre-catalysts for the hydroamination of 1,3-carbodiimides. Whilst the reaction scope is currently limited to reactions of aromatic amines with 1,3-dialkylcarbodiimides, in most cases preparations in hydrocarbon solvents proceed rapidly at room temperature with catalyst loadings as low as 0.2 mol-% and the guanidine reaction products crystallize directly from the reaction mixture. Initial studies are consistent with the intermediacy of heavier group-2 guanidinate complexes.

Original languageEnglish
Pages (from-to)4173-4179
Number of pages7
JournalEuropean Journal of Inorganic Chemistry
Issue number26
DOIs
Publication statusPublished - 1 Sep 2008

Keywords

  • Alkaline earth amides
  • Guanidinate
  • Guanidine
  • Hydroamination

ASJC Scopus subject areas

  • Inorganic Chemistry

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