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Updated: Feb 20, 2026

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV
Published on: December 29, 2016
Catalytic Carbon-Chlorine Bond Activation by Selenium-Based Chalcogen Bond Donors
Patrick Wonner1, Lukas Vogel1, Florian Kniep1
1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum, Germany.
Abstract:
Chalcogen bonding is a noncovalent interaction based on electrophilic chalcogen substituents, which shares many similarities with the more well-known hydrogen and halogen bonding. Herein, the first application of selenium-based chalcogen bond donors in organocatalysis is described. Cationic bifunctionalized organoselenium compounds activate the carbon-chlorine bond of 1-chloroisochroman in a benchmark reaction. While imidazolium-based derivatives showed no noticeable activation, benzimidazolium backbones yielded potent catalysts. In all cases, syn-isomers were markedly more active, presumably due to bidentate coordination, which was confirmed by DFT calculations. Comparison experiments with the corresponding non-selenated as well as the non-cationic reference compounds clearly indicate that the catalytic activity can be ascribed to chalcogen bonding. The rate acceleration by the catalyst-compared to the non-selenated derivative-was about 10 fold.
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