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Tribromides refer to organic compounds that have a linear tribromide anion. Organic tribromides belong to a growing group of organic reagents that are employed in organic transformations largely because of their ease of preparation, mild reaction conditions, and environmentally benign nature. As brominating agents, they have obviated the use of liquid elemental bromine. Tetraalkylphosphonium tribromides are both room temperature ionic liquids and brominating agents, circumventing the use of other solvents and liquid bromine. The ease of isolating tribromide products makes them useful additions to the emerging list of halogenating reagents.
Tribromides are also versatile reagents used in bromination reactions, acylations, and sulfide oxidations. Pyridinium tribromide is utilized in the oxidation of sulfides to corresponding sulfoxides. A catalytic amount of pyridinium tribromide selectively deprotects alcohols with TBS (tri-tert-butylsilyl) protection in the presence of other protecting groups. Organic tribromides are invoked in carbonyl chemistry, particularly as reagents to protect or deprotect carbonyl compounds. Tetrabutylammonium tribromide finds use as an efficient generator of HBr and is employed for the chemoselective acetalization of aldehydes, while methyltriphenylphosphonium tribromide has been found to act as an efficient and mild dethioketalization reagent. Carboxyethyltriphenylphosphonium tribromide finds application as a catalyst in the silylation of alcohols and thiols under solvent-free conditions.