Synlett 2016; 27(11): 1618-1634
DOI: 10.1055/s-0035-1562024
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© Georg Thieme Verlag Stuttgart · New York

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

Kamal Krishna Rajbongshi
Department of Chemistry, Gauhati University, Guwahati, Assam, 781014, India   Email: pphukan@yahoo.com
,
Arun Jyoti Borah
Department of Chemistry, Gauhati University, Guwahati, Assam, 781014, India   Email: pphukan@yahoo.com
,
Prodeep Phukan*
Department of Chemistry, Gauhati University, Guwahati, Assam, 781014, India   Email: pphukan@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 27 December 2015

Accepted after revision: 08 March 2016

Publication Date:
14 April 2016 (online)


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

 
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