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DOI: 10.1055/s-0029-1216645
Pyridinium Hydrobromide Perbromide: A Versatile Reagent in Organic Synthesis
Publication History
Publication Date:
07 May 2009 (online)
Introduction
Pyridinium hydrobromide perbromide (PHPB) has been extensively used in organic synthesis as a selective brominating reagent for alkenes, [¹-5] alkanes, [6] arenes, [7] ketones, [7] [8] anilines, [9] aromatic ethers, [¹0] N-heterocycles, [¹¹] and oxidizing reagents. [¹²] [¹³] PHPB forms red prismatic crystals and its melting point is at 134 ˚C. Further, it is easy to handle, stable and environmentally safe. [¹4] PHPB has been used for regioselective heterocyclization of ortho-cyclohexenyl phenols [¹5] and ipsobromodeformylation in o-hydroxy and o-methoxy substituted aromatic aldehydes. [¹6] It was also found to be a useful catalyst for the chemoselective deprotection of primary TBS and TES ethers, [¹7] hydrolysis of thioacetals, [¹8] and hydroamination of activated styrenes. [¹9]
Pyridinium hydrobromide perbromide is commercially available, but it can be readily prepared by adding one mole of bromine to one mole of pyridine in 48% hydrobromic acid solution. [¹4]
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