A General Method for the Dibromination of Vicinal sp 3 C-H Bonds Exploiting Weak Solvent-Substrate Noncovalent Interactions

A general procedure of 1,2-dibromination of vicinal sp C-H bonds of arylethanes using -bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes,...

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Bibliographic Details
Published in:Organic letters 2021-04, Vol.23 (7), p.2399-2404
Main Authors: Qi, Zaojuan, Li, Weihe, Niu, Yanning, Benassi, Enrico, Qian, Bo
Format: Article
Language:English
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Summary:A general procedure of 1,2-dibromination of vicinal sp C-H bonds of arylethanes using -bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes, quantitatively evaluated via quantum chemical calculations, allows us to circumvent the fact that arylethane ethane cannot be dibrominated through traditional methods. The mechanism was explored by both experiments and quantum chemical calculations, revealing a radical chain with HAA process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c04235