Facile Access to Stable Silylium Ions Stabilized by N-Heterocyclic Imines.

Oxidative N-Heterocyclic Carbene-Catalyzed γ-Carbon Addition of Enals to Imines: Mechanistic Studies and Access to Antimicrobial Compounds.

The reaction mechanism of the γ-carbon addition of enal to imine under oxidative N-heterocyclic carbene catalysis is studied experimentally. The oxidation, γ-carbon deprotonation, and nucleophilic addition of γ-carbon to imine were found to be facile steps. The results of our study also provide highly enantioselective access to tricyclic sulfonyl amides that exhibit interesting antimicrobial ac...

A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis† †Electronic supplementary information (ESI) available: Synthetic and spectral details are deposited. CCDC 1035566–1035574. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc03675a

Silaimidazolium and silaimidazolidinium ions.

2-Silaimidazolium ions and 2-silaimidazolidinium ions were synthesized by Lewis acid-base adduct formation between N-heterocyclic silylenes and silyl arenium ions. They were isolated in high yields as their [B(C(6)F(5))(4)](-) salts. These salts are stable at room temperature and were characterized by NMR spectroscopy supported by the results of density functional computations of molecular stru...

Frustrated N-heterocyclic carbene-silylium ion Lewis pairs.

The reaction of the N-heterocyclic carbene 1,3-di-tert-butyl-4,5-dimethylimidazolin-2-ylidene () with trimethylsilyl iodide, triflate and triflimidate [Me3SiX, X = I, CF3SO3 (OTf), (CF3SO2)2N (NTf2)] by mixing the neat, liquid starting materials afforded the corresponding 2-(trimethylsilyl)imidazolium salts [()SiMe3]X as highly reactive, white crystalline solids. Only the triflimidate (X = NTf2...

A Facile and Environmental Friendly Method for C=N Bond Cleavage of Imines Using p-Toluenesulfonic Acid in Solid State

A simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter reaction times, cheap processing, high yields of product and easy availability of the catalyst. ...