Elemental Sulfur-Mediated Aromatic Halogenation
Junpei Matsuoka, Yuna Yano, Yuuka Hirose, Koushi Mashiba, Nanako Sawada, Akira Nakamura, Tomohiro Maegawa
Abstract
A method for aromatic halogenation using a combination of elemental sulfur (S 8 ) and N -halosuccinimide has been developed. A catalytic quantity of elemental sulfur (S 8 ) with N -bromosuccinimide (NBS) and N -chlorosuccinimide (NCS) effectively halogenated less-reactive aromatic compounds, such as ester-, cyano-, and nitro-substituted anisole derivatives. No reaction occurred in the absence of S 8, underscoring its crucial role in the catalytic activity. This catalytic system was also applicable to aromatic iodination with 1,3-diiodo-5,5-dimethylhydantoin.
Topics & Concepts
AnisoleHalogenationSulfurCatalysisChemistryOrganic chemistryAromaticityNitroElemental analysisElectrophilic aromatic substitutionMoleculeAlkylVanadium and Halogenation ChemistryOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions