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Updated: Jul 3, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Synthesis of electronically diverse tetraarylimidazolylidene carbenes via catalytic aldimine coupling
James W Ogle1, Jubo Zhang, Joseph H Reibenspies
1Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, USA.
Abstract:
A new method for synthesizing symmetrical N-heterocyclic imidazolium salts is described. Catalytic coupling of aldimines with cyanide followed by oxidation gives alpha-diketimines, which can then be cyclized with formaldehyde in acidic media. This two-step procedure requires no chromatography and allows the synthesis of electronically diverse 1,3,4,5-tetraarylimidazolylidene carbenes.
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