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

作者：Rajbongshi Kamal Krishna; Borah Arun Jyoti; Phukan Prodeep^*

来源：Synlett, 2016, 27(11): 1618-1634.

DOI：10.1055/s-0035-1562024

• TsNBr2
• cohalogenation
• oxidation
• nitrene
• bromination

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

• 出版日期2016-7