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Updated: Mar 27, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Unusual Fragmentation and Transformation of an N-Heterocyclic Carbene by a Stable Phosphonium-Borane
Yufei Li1, Soren K Mellerup1, Francoise Sauriol1
1Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada.
Abstract:
A 1-phosphonium-8-borane-decorated naphthalene molecule 2 has been found to react with N,N'-dimethylimidazol-2-ylidene (IMe), a popular member of the N-heterocyclic carbene (NHC) family, which converts it into two vinyl-amine fragments one of which is trapped between the phosphonium and borane unit by the formation of a C-C and a B-N bond. The same reactivity was not observed for larger NHC molecules. Control experiments and mechanistic studies have established the involvement of an ylide-borane molecule and an imidazolium salt in addition to IMe carbene in this new transformation of an NHC.
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