title: Reactivity of an NHC-stabilized silylene towards ketones. Formation of silicon bis-enolates vs. bis-silylation of the C[double bond, length as m-dash]O bond.
abstract: The NHC-stabilized silylaminosilylene Ar(SiMe3)N(Cl)Si(IiPr) (, Ar = 2,6-iPr2C6H3, IiPr = 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene) reacted rapidly with a series of enolizable ketones under ambient conditions in a stereo- and regioselective fashion to afford silicon bis-enolates () in high yields with the elimination of imidazolium salt. In contrast, reaction of with two equivalents of benzophenone led to a slow bis-silylation of the C[double bond, length as m-dash]O double bond. All of the products have been characterized by (1)H, (13)C, and (29)Si NMR spectroscopy and HR-MS analysis. The configurations of compounds were determined by NOESY experiments.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China. cmcui@nankai.edu.cn.
authors.forename: Yao
authors.initials: Y
authors.lastname: Li
authors.forename: Bing
authors.initials: B
authors.lastname: Ma
authors.forename: Chunming
authors.initials: C
authors.lastname: Cui