N-heterocyclic olefins (NHOs), a derivative of the popular N-heterocyclic carbene ligand, are a relatively new class of ylide-type donors which have been shown to exhibit stabilization of low valent metal species. With a similar steric structure but weaker electron donation than their NHC counterparts, NHO ligands are likely to exhibit diverging bonding patterns that may potentially lead to new reactivity with promise for catalytic applications. This work describes an efficient, four-step synthesis of the NHO IPrCH2 (IPr ꞊ [HCNDipp]2C, Dipp ꞊ 2,6-diisopropylphenyl) from 2,6-diisopropylaniline in good yield. A survey of its capability to ligate early transition metals is also reported. 1H and 13C NMR spectroscopy were employed to verify the identity and structure of the generated [IPrCH2]xM coordination complexes. Finally, the possibility of changing the R-groups on the NHO unit, and its consequent effects on the bonding and stabilization of metal cations is under exploration.