N,N-Dibromo-p-Toluenesulfonamide (TsNBr₂): A Promising Alternative Bromo-Organic Reagent

Abstract

N,N-Dihalosulfonamides are important reagents for various organic transformations. Simplicity, efficiency, and a unique chemical behaviour make this class of compounds synthetically useful. N,N-Dibromo-p-toluenesulfonamide (TsNBr₂) is an efficient source of electrophilic bromine, which, at the same time, also provides the nucleophilic sulfonamide counterpart to form a C–N bond. This reagent has also been found to be a suitable precursor of nitrene. These diverse properties led to the development of various important organic transformations under catalyst-free and relatively mild reaction conditions. However, the strong oxidizing nature of this reagent sometimes appears as a limitation for a desired functional group transformation.

 1 Introduction

 2 Cohalogenation of Olefins

 3 Activation of Alkynes with TsNBr₂

 4 Oxidation Reactions

 5 Nitrene Transfer Reactions

 6 Hofmann Rearrangement Using TsNBr₂

 7 Bromination of Aromatic Compounds

 8 Cleavage of Oximes

 9 Miscellaneous Reactions

10 Conclusion

Key words

TsNBr₂ - cohalogenation - oxidation - nitrene - bromination

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