Li, Yudong published the artcileProton Transfer Can Govern Regioselectivity Assisted by Iron Catalysis, Application of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is iScience (2020), 23(6), 101214, database is CAplus and MEDLINE.
Ortho-selective aromatic C-H functionalization is frequently used in organic synthesis and chem./pharmaceutical industries. However, this reaction relies heavily on the use of directing groups suffering from limited substrate scope and extra steps to put on and remove the directing/protecting groups. Herein authors present the previously neglected concept that enables good to nearly complete selective ortho position. Proton transfer was utilized to tune the electron d. on the aryl ring and determine the positional selectivity of electrophilic substitution. Consistently with deuteration experiments and DFT studies, this work demonstrates that acid-promoted proton transfer directs accelerated ortho-selective halogenation of NH/OH contained aromatic amines/phenols with excellent selectivity (>40 examples; up to 98:2 ortho/para selectivity). The application potential of this Fe-catalyzed method is demonstrated by the convenient synthesis of three alkaloids and tizanidine. This report raises the possibility that proton transfer could serve as the basis of developing new selective C-H functionalization reactions.
iScience published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Application of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.
Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica