An environmentally benign synthesis of organic ammonium tribromides (OATB) and bromination of selected organic substrates by tetrabutylammonium tribromide (TBATB)

Halogen Interactions in 2,4,5-Tribromoimidazolium Salts

“…2,4,5-Tribromoimidazole [CARN 2034-22-2], first described in 1877 [1], is readily prepared by bromination of imidazole [2][3][4][5][6][7]. It has been found in nature [8] and is an effective fire-retardant agent [9].…”

Synthesis and Crystal Structure Determination of [H2‐cryptand 222](Br3)2: A Unique Tribromide Catalyst for the Catalytic Chemoselective N‐Boc Protection of Amines

“…24 Given the usefulness of such compounds, the development of further synthetic protocols for their synthesis is an area of interest. 25,26 Due to its great stability under the conditions used in various base-catalyzed nucleophilic substitutions and catalytic hydrogenation reactions, the tert-butoxycarbonyl (boc) group is perhaps one of the most important protecting groups, especially for amines and amine derivatives. 27,28 The stability of N-boc to catalytic hydrogenation and its resistance towards basic and nucleophilic attack make carbamates and benzyl esters ideal orthogonal partners for the protection of amines during the synthesis of multifunctional targets.…”

Synthesis, Characterization and Structure of DBU-hydrobromide-perbromide: A Novel Oxidizing Agent for Selective Oxidation of Alcohols to Carbonyl Compounds

“…1 Organic tribromide salts as mild reagents are good candidates for this selective conversion, because they are not only stable, crystalline solids, and relatively soluble in most organic solvents but also can be handled more conveniently than liquid bromine and can be used successfully for this purpose. Although they are used as brominating agents of aromatic rings, 2 α-bromination of ketones, [3][4][5][6] and ketals, 3,7 electrophilic addition, 3,4,[8][9][10][11][12][13][14] and substitution, 4,13,[15][16][17][18][19] they are also used as catalyst for the oxidation of aromatic aldehydes to carboxylic acids 20 or ω-bromoesters, 21 and dialkyl and alkyl aryl sulfides to sulfoxides, 22 protection of carbonyl, 23 and hydroxyl groups, 24 cleavage of ethers and dithioacetals 25 and conversion of thioamides into amides. 26 They can also be applied in the synthesis of heterocyclic ring systems such as aziridines 27 and benzothiazoles.…”