Lithium Aryltrifluoroborate as a Catalyst for Halogen Transfer

The catalysis of two successive bromine–lithium exchange reactions, referred to as a “halogen dance”, by lithium aryltrifluoroborate is reported. At a loading of 10 mol %, this catalyst exhibited efficient activity for bromo group transfer and was applicable to various brominated pyridines. Density...

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Bibliographic Details
Published in:ACS catalysis 2023-03, Vol.13 (6), p.3788-3793
Main Authors: Inoue, Kengo, Hirano, Keiichi, Fujioka, Shota, Uchiyama, Masanobu, Mori, Atsunori, Okano, Kentaro
Format: Article
Language:English
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Summary:The catalysis of two successive bromine–lithium exchange reactions, referred to as a “halogen dance”, by lithium aryltrifluoroborate is reported. At a loading of 10 mol %, this catalyst exhibited efficient activity for bromo group transfer and was applicable to various brominated pyridines. Density functional theory calculations were consistent with the proposed mechanism, where the catalyst provided a bromine atom to the mono- or dibrominated substrate and the resulting debrominated catalyst then abstracted another bromine atom from the di- or tribrominated substrate, leading to the transposition of the bromo group on the substrate with catalyst regeneration.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c06082