Cycloelimination of Imidazolidin‐2‐ylidene N‐Heterocyclic Carbenes: Mechanism and Insights into the Synthesis of Stable “NHC‐CDI” Amidinates |
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| Authors: | Aleksandr V. Zhukhovitskiy Julie Geng Prof. Dr. Jeremiah A. Johnson |
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| Affiliation: | Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA) |
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| Abstract: | We report the discovery that 1,3‐bis(aryl)imidazolidin‐2‐ylidenes, one of the most widely studied classes of N‐heterocyclic carbenes (NHCs), undergo quantitative conversion to zwitterionic “NHC‐CDI” amidinates upon heating to ≈100 °C in solution. The mechanism of this novel NHC decomposition process is studied in detail. These studies enabled the rational synthesis of a new class of bench stable amidinates from a panel of NHCs and carbodiimides. We expect these constructs to find utility in a variety of applications. |
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| Keywords: | amidinate carbene carbodiimide cycloelimination decomposition pericyclic reaction |
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