Related Experiment Video
Updated: Sep 4, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
N-Boron-Functionalized Anionic N-Heterocyclic Carbenes (NBA-NHCs)-A Case Study
Sophie Mann1, Günther Horrer1, Maik Finze1,2
1Institute of Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Würzburg, Germany.
Abstract:
The synthesis and characterization of a new family of N-boron-functionalized anionic NHCs (NBA-NHCs), IiPrB(CN)3 - (5), IiPr(C2F5)BF2 - (6), IMesB(CN)3 - (7), and IMes(C2F5)BF2 - (8), accessible on gram-scale from air- and moisture-stable precursors, is reported. Multinuclear NMR, IR spectroscopy, and single-crystal X-ray diffraction confirm highly electron-rich carbenic carbon centers and strengthened B-N interactions in these molecules. Selenium adducts 9-12 of these NBA-NHCs indicate an enhanced π-acceptor character relative to neutral NHCs, while Tolman electronic parameters of nickel tricarbonyl complexes [(NBA-NHC)Ni(CO)3]-K+ 13-16 demonstrate their strong donor ability, similar to dianionic carbenes. Steric maps and buried volume (%Vbur) analyses of linear gold(I) complexes [(NBA-NHC)Au(PPh3)] 17-20 reveal tunable steric profiles, ranging from anisotropic to strongly shielding environments by varying the N-substituents. These results establish NBA-NHCs as a modular ligand platform enabling control of electronic properties and steric demand at the metal center for future applications in coordination chemistry and catalysis.
More Related Videos
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
08:40Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
Published on: December 6, 2021
Related Concept Videos
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Electrophilic Aromatic Substitution: Nitration of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition
Nomenclature of Aryl and Heterocyclic Amines
Hydroboration-Oxidation of Alkenes
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.