3 years ago

Calcium Hydride Reactivity: Formation of an Anionic N-Heterocyclic Olefin Ligand

Calcium Hydride Reactivity: Formation of an Anionic N-Heterocyclic Olefin Ligand
Holger Elsen, Sjoerd Harder, Jürgen Pahl, Andrea Causero
An anionic N-heterocyclic olefin ligand was serendipitously obtained by reaction of an amidinate calcium hydride complex with 1,3-dimethyl-2-methyleneimidazole (NHO). Instead of anticipated addition to the polarized C=CH2 bond to form an unstabilized alkylcalcium complex, deprotonation of the NHO ligand in the backbone was observed. Preference for deprotonation versus addition is explained by loss of aromaticity in the latter conversion. Theoretical calculations demonstrate the substantially increased ylidic character of this anionic NHO ligand which, like N-heterocyclic dicarbenes, shows strong bifunctional coordination. Extended family: The reaction of a calcium hydride complex with an N-heterocyclic olefin (NHO) gave a new bifunctional NHC-based ligand which shows strongly increased ylide character in comparison to the parent NHO.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703037

You might also like
Never Miss Important Research

Researcher is an app designed by academics, for academics. Create a personalised feed in two minutes.
Choose from over 15,000 academics journals covering ten research areas then let Researcher deliver you papers tailored to your interests each day.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.