Related Experiment Video
Updated: Nov 21, 2025

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Mukaiyama aldol reaction catalyzed by (benz)imidazolium-based halogen bond donors
Revannath L Sutar1, Nikita Erochok1, Stefan M Huber1
1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum, Germany. stefan.m.huber@rub.de.
Abstract:
A series of cationic monodentate and bidentate iodo(benz)imidazolium-based halogen bond (XB) donors were employed as catalysts in a Mukaiyama aldol reaction. While 5 mol% of a monodentate variant showed noticeable activity, a syn-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BArF4 salts, PF6 or OTf salts were either inactive or showed background reaction through Lewis base catalysis. Repetition experiments clearly ruled out a potential hidden catalysis by elemental iodine and demonstrated the stability of our catalyst over three consecutive cycles.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Related Concept Videos
Base-Promoted α-Halogenation of Aldehydes and Ketones
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Base-Catalyzed Aldol Addition Reaction
Acid-Catalyzed Aldol Addition Reaction
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...