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Carbon-Halogen Bond Activation by Selenium-Based Chalcogen Bonding.


ABSTRACT: 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.

SUBMITTER: Wonner P 

PROVIDER: S-EPMC5638094 | biostudies-literature |

REPOSITORIES: biostudies-literature

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