Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 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

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