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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 | 2017 Sep

REPOSITORIES: biostudies-literature

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

Wonner Patrick P Vogel Lukas L Düser Maximilian M Gomes Luís L Kniep Florian F Mallick Bert B Werz Daniel B DB Huber Stefan M SM

Angewandte Chemie (International ed. in English) 20170706 39

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 prov ...[more]

PMID: 28605080

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