1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality

Abstract

Keywords:

N-Halosuccinimides as Precatalysts for C-, N-, O-, and X-Nucleophilic Substitution Reactions of Alcohols under Mild Reaction Conditions

“…The assumption that NXSs are actually precatalysts producing HOX, X2, and protons during the process while these species could catalyze nucleophilic substitutions seems to be reasonable [37]. The assumption that NXSs are actually precatalysts producing HOX, X 2 , and protons during the process while these species could catalyze nucleophilic substitutions seems to be reasonable [37].…”

“…The assumption that NXSs are actually precatalysts producing HOX, X2, and protons during the process while these species could catalyze nucleophilic substitutions seems to be reasonable [37]. The assumption that NXSs are actually precatalysts producing HOX, X 2 , and protons during the process while these species could catalyze nucleophilic substitutions seems to be reasonable [37]. The discrimination between the oxidation process observed in the case of the use of molar excess of NXSs (1.3 to 2 equivalent excess) [26][27][28] was achieved using substoichiometric amounts of NIS and by the selection of alcohols, which could after realizing hydroxyl group form, through resonance or strong inductive effect, stabilize carbocation intermediates which readily collapse with present nucleophile sources.…”

Direct Cross-Coupling of Alcohols with O-Nucleophiles Mediated by N-Iodosuccinimide as a Precatalyst under Mild Reaction Conditions

“…It could be seen that the formation of water through the etherification reaction as the only by-product of the reaction could accelerate the reaction. The assumption that NIS was a precatalyst providing HOI, I 2 , and protons during the system, which could correspond to nucleophilic substitution acceleration, was indicated to be reasonable [15,18]. To get insight into the precatalyst's thermal stability, thermal gravimetric analysis (TGA) on the NIS was accomplished.…”

“…With our continuous research work on improving and developing greener protocols [16][17][18][19], we now report the expanding role of NIS as a commercially available, metalfree, and easy-to-handle precatalyst for direct dehydrative O-alkylation reactions between various alcohols under high-substrate concentration reaction conditions (HCRC), and leading to a practical, efficient, selective, and easily scalable method.…”

The Application of Dibromohydantoin in Chemical Experiment Pedagogy

“…Consequently, these limitations hinder its widespread adoption and utilization in undergraduate experiments. The compound dibromohydantoin is commonly employed as a disinfectant in everyday life and serves as a specialized brominating agent. , In comparison to other brominating agents like NBS, 1,3-dibromo-5,5-dimethylhydantoin (dibromohydantoin) exhibits the advantages of possessing high active bromine content and excellent storage stability. , However, its application in α-bromination reactions of acetophenone derivatives has been scarcely investigated thus far. Therefore, this study aims to investigate the influence of the solvent, catalysts, and reactants on the α-bromination reaction of acetophenone and its derivatives using a controlled variable approach.…”