June 2023

The use of an air-stable cationic hemiboronic acid catalyst for the chemoselective reduction of enones is described. By changing the identity and stoichiometry of the silane reducing agent, either the conjugate reduction products or the fully reduced products can be obtained in high selectivity. In contrast to analogous reactions catalyzed by air- and moisture-sensitive borane catalysts, the hemiboronic acid catalyzed protocol can be performed under ambient conditions. Profiling studies revealed that global reduction proceeds via a rapid initial 1,4-addition, followed by ketone deoxygenation with a rate that is highly silane-dependent.

Bromamine-T (BAT) is a notable member of a special class of compounds called organic haloamines, which are oxidising agents. It can act as the source of halonium ions, hypohalite species, and N-anions, whilst also displaying basic and nucleophilic properties. Bromamine-T finds wide application as an efficient reagent for various organic transformations, such as aminobromination, amination, oxidation, and others. It can be used under mild conditions and has low toxicity. Moreover, due to its immense biological significance, this reagent is piquing the interest of many researchers.1 Introduction1.1 The Sodium Salt of N-Bromo-p-toluenesulfonamide (Bromamine-T or TsNBrNa): Reagent Overview1.2 Physical Properties of Bromamine-T1.3 Preparation and Characterisation of Bromamine-T2 Biological Significance of Bromamine-T3 Organic Transformations Using Bromamine-T3.1 Aminobromination3.2 Amination3.3 Aminohydroxylation3.4 Aziridination3.5 Bromination3.6 Oxidation: Kinetic and Mechanistic Studies4 Conclusion