The Role of (BDMS) Bromodimethylsulfonium bromide as a Catalyst and Brominating Reagent: A Concise Overview

Abstract

Bromodimethylsulfonium bromide (BDMS) is an expedient storage of molecular bromine or bromine radicals or bromonium ions and also of nucleophilic bromide ion. It is an easily available, inexpensive and versatile reagent. It is used as an effective brominating reagent as well as a valuable catalyst for several organic conversions. The prominent characteristics of this compound are the straight forwardness of the process, the ease of access of the compound, no requirement of chromatographic separation, no additional base, Lewis acid, or any other catalyst, better yields in comparatively less reaction times and assist to maintain the stoichiometric ratio during the reactions. The present article includes the catalytic applications as well as its brominating role in organic reactions.

Visible-light-induced C(sp3)–H bromination of 4-methylthiophene derivatives with HBr/H2O2

“…3 Generally, the methyl group on the thiophene ring can be brominated with molecular bromine, and the brominated moiety can couple with other pharmacophores to afford various bioactive molecules, providing compound libraries for the discovery of new drugs. 4…”

Recent progress in the oxidative bromination of arenes and heteroarenes

“…There are several main routes for the bromination of arenes and heteroarenes, such as electrophilic bromination, 4 oxidative bromination, 5 transition-metal catalyzed bromination through C–H activation 6 and other ways including enzymatic bromination and bromination through a radical pathway. 7 Traditionally, electrophilic bromination has always been used for generating organic bromides.…”

Optimization of Catalytic Bromination of Acetophenones Using Taguchi's Method

“…[19] In view of above limitations as well as in persistence of our attempt in the area of novel synthetic methodologies we have designed a novel and enhanced protocol for regioselective αmonobromination of a broad series of acetophenones. BDMS has been utilized in variety of organic conversions [20,21] e. g. conversion of alcohols to the subsequent bromides, [22] disulfides via thiols oxidation, [23] dithioacetals deprotection [24] and equivalent enones from the α-bromoenones. [25] In contrast with the earlier reported methods it offers a number of advantages, e. g., the reagent BDMS is eagerly reachable, can be consider a suitable storage space of molecular bromine less dangerous [26][27][28] and simple to grip, and while carrying out the reactions it facilitates in maintaining the stoichiometric ratio (Scheme 1).…”