Publication: Halogen bond-induced electrophilic aromatic halogenations
Issued Date
2021-09-21
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14770520
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2-s2.0-85115108078
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Mahidol University
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SCOPUS
Bibliographic Citation
Organic and Biomolecular Chemistry. Vol.19, No.35 (2021), 7518-7534
Suggested Citation
Wanutcha Lorpaiboon, Pakorn Bovonsombat Halogen bond-induced electrophilic aromatic halogenations. Organic and Biomolecular Chemistry. Vol.19, No.35 (2021), 7518-7534. doi:10.1039/d1ob00936b Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/76022
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Title
Halogen bond-induced electrophilic aromatic halogenations
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Abstract
In recent years, there has been increasing interest in utilising halogen bonds in organic synthesis, especially in aromatic halogenation reactions.N-Halosuccinimides and 1,3-dihalo-5,5-dimethylhydantoins are popular sources of halonium ions due to their ease of handling and low toxicities. Traditionally, theseN-haloimides are activated by electrophiles, namely Brønsted and Lewis acids. The recent discovery of possible activation by nucleophilic Lewis base catalysts led to a paradigm shift in aromatic halogenation. Active functional motifs in Lewis base catalysts such as C S, R-S-R1, Ar-S-S-Ar, S O, Ar-NH2, and R2NH+Cl−form halogen bonds with the positively charged σ-hole of the halogen atoms: an essential interaction to produce halonium ions. This review highlights the evolution of the two modes of activation. Evidence of halogen bond formation from mechanistic studies of nucleophilic activation is also discussed herein.