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Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV
Published on: December 29, 2016
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Carbon-Halogen Bond Activation by Selenium-Based Chalcogen Bonding
Patrick Wonner1, Lukas Vogel1, Maximilian Düser1
1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44801, Bochum, Germany.
Angewandte Chemie (International Ed. in English)
|June 13, 2017
Summary
Selenium-based chalcogen bond donors show promise as Lewis acids in organic synthesis. These novel donors accelerate reactions like benzhydryl bromide solvolysis more effectively than traditional halogen bond donors.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
- Noncovalent Interactions
Background:
- Chalcogen bonding is an under-explored noncovalent interaction analogous to halogen bonding.
- The application of chalcogen bonding in catalysis and organic synthesis remains limited.
Purpose of the Study:
- To investigate the first application of selenium-based chalcogen bond donors as Lewis acids in organic synthesis.
- To evaluate the efficacy of these donors in promoting chemical reactions.
Main Methods:
- The solvolysis of benzhydryl bromide was employed as a benchmark halide abstraction reaction.
- Comparative experiments were conducted using chalcogen bond donors with a bis(benzimidazolium) core and a brominated halogen bond donor.
Main Results:
- Chalcogen bond donors accelerated the reaction rate by a factor of 20-30 compared to background reactivity.
- Evidence suggests the observed rate acceleration is attributable to chalcogen bonding interactions.
- The selenium-based chalcogen bond donors outperformed a related brominated halogen bond donor.
Conclusions:
- Selenium-based chalcogen bonding represents a novel and effective Lewis acid activation strategy in organic synthesis.
- This study highlights the potential of chalcogen bonding as a powerful tool for chemical transformations.
- Chalcogen bond donors offer a promising alternative to halogen bond donors in catalytic applications.
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