Imidazolium Dicyanomethylides as N‐Ylide Precursors of Anionic N‐Heterocyclic Carbenes
Kahnert, S. R., Namyslo, J. C., Rissanen, K., Nieger, M., & Schmidt, A. (2024). Imidazolium Dicyanomethylides as N‐Ylide Precursors of Anionic N‐Heterocyclic Carbenes. European Journal of Organic Chemistry, Early View. https://doi.org/10.1002/ejoc.202400163
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European Journal of Organic ChemistryDate
2024Copyright
© 2024 The Authors. European Journal of Organic Chemistry published by
Wiley-VCH GmbH
In the past, the use of nitrogen ylides focused primarily on cycloadditions, where the 1,3-dipole was used as a building block for the formation of heterocycles such as pyrroles or pyrrolinones. In this work, we present a new perspective on imidazolium dicyanomethylides with their synthesis and utilization as anionic N-heterocyclic carbenes (NHCs). The values of relative carbene formation energies (CREF) for a wide range of substituted imidazolium ylides unknown in the literature showed promising properties. In situ trapping reactions of these anionic NHCs with selenium led to anionic, water-soluble compounds that exhibited remarkable coordination behavior according to X-ray structure analyses. In addition, the 77Se shifts of the investigated compounds were measured to draw conclusions about their π-acceptance.
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