Application of N-halo reagents in organic synthesis

Abstract

This review article summarizes published data on the application of N-halo reagents (such as N-halo amines, N-halo amides and/or imides, N-halo sulfonamides and/or imides, and etc.) in various organic functional group transformations such as: oxidation reactions, deprotection and protection of different functional groups, halogenation of saturated and unsaturated compounds, acylation of alcohols, phenols, amines or thiols, epoxidation of alkenes, aziridination and etc. The main purpose of writing this review is encouraging of active researchers interested to this field for the synthesis of new N-halo reagents specially with different halogens and applications of these new N-halo reagents in organic reactions or finding more and more applications of existing N-halo reagents in organic synthesis.

A Green Protocol for the Bromination and Iodination of the Aromatic Compounds using H5IO6/NaBr and H5IO6/NaI in the Water

“…Recently, the oxidative halogenation of organic compounds by halides have emerged as an important alternative for the synthesis of such haloderivatives. [19][20][21][22][23][24][25][26][27][28][29][30] Despite the broad choice of options, however, many bromination and iodination methodologies are cumbersome, costly and harsh or involve the use of toxic heavy metals, volatile organic solvents, or elemental halogenes which are highly corrosive, toxic or self-sublimating. In addition, there are some environmental hazards with respect to handling them.…”

Kinetics Studies of Oxidation of Furosemide by Acidic Potassium Permanganate

“…By keeping constant concentration of potassium permanganate and H 2 SO 4 and by changing the concentration of Furosemide increases the rate of reaction (Table-1) the plot of log of k obs versus log concentration of Furosemide for different initial concentration of metal complex is linear with unit slop, which shows that the first order dependence of rate of reaction on Furosemide [18][19][20] . …”

PdCl2 Catalyzed and Uncatalyzed N-Oxidation of Naratriptan with Alkaline Chloramine-T: Delineation of Reaction Mechanisms and Kinetic Modelings

“…Their versatile nature is due to their ability to act as source of halonium cations, hypohalite species and N-anions which act both as bases and nucleophiles [5]. As a result, these reagents react with a wide range of functional groups affecting an array of molecular transformations [6][7][8][9]. Sodium N-chloro Ptoluenesulfonamide or chloramine-T (CAT) is the prominent member of this class of compounds and behaves as a mild oxidizing agent in both acidic and alkaline media.…”