title: Unusual Fragmentation and Transformation of an N-Heterocyclic Carbene by a Stable Phosphonium-Borane peri-Functionalized Naphthalene.
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.
authors.affiliation: Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada.
authors.forename: Yufei
authors.initials: Y
authors.lastname: Li
authors.affiliation: Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada.
authors.forename: Soren K
authors.initials: SK
authors.lastname: Mellerup
authors.affiliation: Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada.
authors.forename: Francoise
authors.initials: F
authors.lastname: Sauriol
authors.affiliation: Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada.
authors.forename: Gabriele
authors.initials: G
authors.lastname: Schatte
authors.affiliation: Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada. suning.wang@chem.queensu.ca, sw17@queensu.ca, wangsn14@bit.edu.cn.|Beijing Key Laboratory of Photoelectronic/Electrophotonic, Conversion Materials, School of Chemistry, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing, P.R. China. suning.wang@chem.queensu.ca, sw17@queensu.ca, wangsn14@bit.edu.cn.
authors.forename: Suning
authors.identifier: http://orcid.org/0000-0003-0889-251X
authors.initials: S
authors.lastname: Wang
keywords: N-heterocyclic carbenes; boranes; cleavage reactions; phosphonium; ylides