Unusual Fragmentation and Transformation of an N‐Heterocyclic Carbene by a Stable Phosphonium–Borane peri‐Functionalized Naphthalene |
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| Authors: | Yufei Li Soren K Mellerup Francoise Sauriol Gabriele Schatte Prof?Dr Suning Wang |
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| Affiliation: | 1. Department of Chemistry, Queen's University, Kingston, Ontario, Canada;2. Beijing Key Laboratory of Photoelectronic/Electrophotonic, Conversion Materials, School of Chemistry, Beijing Institute of Technology, Beijing, P.R. China |
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| 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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| Keywords: | boranes cleavage reactions N-heterocyclic carbenes phosphonium ylides |
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