Theoretical study on the catalytic reactivity of N-hydroxyphthalimide tuned by different heterocyclic substitutions on its phenyl ring for aerobic oxidation

• Published in: Chemical physics letters 2016-07, Vol.657, p.135-141
• Main Authors: Chen, Kexian, Xie, Haiying, Jiang, Kezhi, Mao, Jianyong
• Format: Article
• Language: English
• Subjects: Hydrogen-abstraction; N-hydroxyphthalimide; Organocatalysis; Oxidation; Toluene
• ISSN: 0009-2614; 1873-4448
• DOI: 10.1016/j.cplett.2016.05.069

[Display omitted] •The catalysts with heterocyclic replacements on the phenyl ring of NHPI are studied.•The reactivity of catalysts with five-member ring is mostly lower than that of NHPI.•The catalyst with the structure of imidazolium ILs has comparable reactivity to NHPI.•The reactivity of catalysts with two active NOH groups is higher than that of NDHPI. The structure–reactivity relationship of new hydroxyimide organocatalysts based on the heterocyclic replacements of the phenyl ring of N-hydroxyphthalimide (NHPI) has been theoretically investigated to gain a mature understanding of this particular catalysis for aerobic oxidation. We find that the reactivity of catalysts with the common five-member aromatic rings is lower than that of NHPI. The catalyst with the recyclable structure of imidazolium ionic liquid may serve as a novel model catalyst for further improvements due to its reactivity comparable to that of NHPI. The catalytic reactivity of multi-nitroxyl catalysts is theoretically more fascinating than that of the highly efficient N,N-dihydroxypyromellitimide.