Qu, Zheng-Wang; Zhu, Hui; Grimme, Stefan published the artcile< Mechanistic Insights for Aniline-Catalyzed Halogenation Reactions>, Recommanded Product: 1-Chloropyrrolidine-2,5-dione, the main research area is anisole halosuccinimide aniline catalyst halogenation reaction mechanism.
Lewis base catalyzed electrophilic aromatic halogenation using N-halosuccinimides (NsX; X=Cl, Br, I) under mild conditions has attracted much attention, but the detailed mechanism remains elusive. Using the aniline MesNH2 and anisole PhOMe as the typical base catalyst and aromatic substrate, resp., a novel mechanism is revealed by extensive DFT calculations The autogenic protonation of imine XMes=NH (via Mes=NH+ mediated dimerization of MesNH2) is crucial to initialize the electrophilic halonium X+ transfer to nucleophilic substrates. It is shown that the aniline MesNH2 and more basic imine XMes=NH may act as efficient halonium X+ and proton H+ shuttles, resp., connected by the arenium XMesNH2+. Non-coordinating MesNH3+ salts are suggested as efficient catalyst for electrophilic iodination. Without suitable stabilization of the highly basic anion Ns-, the generally accepted concept of Lewis base catalyst as simple X+ shuttle will never work efficiently due to a high thermodn. barrier. In general, autogenic or addnl. acid additives should be used for more efficient Lewis base catalyzed halogenation.
ChemCatChem published new progress about Free energy. 128-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C4H4ClNO2, Recommanded Product: 1-Chloropyrrolidine-2,5-dione.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics