Kinetically Directed Reactivity of Magnesium Dihydropyridides with Organoisocyanates

Michael S. Hill, Dugald J. MacDougall, Gabriele Kociok-Köhn, Mary F. Mahon, Catherine Weetman

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Although reactions between β-diketiminato magnesium species containing monocyclic 1,4-dihydropyridide ligands and the representative ketone benzophenone are observed to provide reduction by formal hydride transfer to yield magnesium diphenylphenoxide, similar reactions with organic isocyanates display only a very limited propensity toward hydride transfer and reduction to amidate species. In these latter systems, reaction primarily takes place with Mg-N insertion to afford O-bound ureide complexes. Further reactions of a magnesium dihydro-isoquinolide complex, which is constrained to hydride dearomatization at the 2-position only, display more variable behavior. Although similar Mg-N insertion and ureide formation is observed for reactions with isocyanates bearing less sterically demanding N-substitution, more bulky isocyanates provide unusual enamide C-C coupling reactivity.

Original languageEnglish
Pages (from-to)2590-2599
Number of pages10
JournalOrganometallics
Volume34
Issue number11
DOIs
Publication statusPublished - 8 Jun 2015

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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