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Unusual Fragmentation and Transformation of an N‐Heterocyclic Carbene by a Stable Phosphonium–Borane peri ‐Functionalized Naphthalene
Author(s) -
Li Yufei,
Mellerup Soren K.,
Sauriol Francoise,
Schatte Gabriele,
Wang Suning
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504156
Subject(s) - phosphonium , carbene , borane , chemistry , ylide , naphthalene , molecule , medicinal chemistry , fragmentation (computing) , ketene , cationic polymerization , polymer chemistry , organic chemistry , catalysis , computer science , operating system
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.