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

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

Angew Chem Int Ed Engl

Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44801, Bochum, Germany.

Published: September 2017

AI Article Synopsis

Article 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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5638094PMC
http://dx.doi.org/10.1002/anie.201704816DOI Listing

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