Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 39, Pages 12009-12012Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201704816
Keywords
chalcogen bonding; chalcogens; Lewis acids; noncovalent interactions; solvolysis
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Funding
- European Research Council (ERC) under European Union's Horizon research and innovation programme [638337]
- European Research Council (ERC) [638337] Funding Source: European Research Council (ERC)
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Chalcogen bonding is a little explored noncovalent interaction similar to halogen bonding. This manuscript describes the first application of selenium-based chalcogen bond donors as Lewis acids in organic synthesis. To this end, the solvolysis of benzhydryl bromide served as a halide abstraction benchmark reaction. Chalcogen bond donors based on a bis(benzimidazolium) core provided rate accelerations relative to the background reactivity by a factor of 20-30. Several comparative experiments provide clear indications that the observed activation is due to chalcogen bonding. The performance of the chalcogen bond donors is superior to that of a related brominated halogen bond donor.
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