On the potential intermediacy of PhIBr 2 as a brominating agent

PhIBr 2 , first purported to exist over 100 years ago, has been subject of few reports due to its low stability. However, a recent publication proposes a reaction of PIFA (PhI(OC(O)-CF 3 ) 2 ) with TMSBr to form PhIBr 2 in situ and demonstrated its efficacy in aryl brominations. This report investig...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 20; no. 43; pp. 8454 - 8460
Main Authors Tania, Molino, Andrew, Sharp-Bucknall, Lachlan, Wilson, David J. D., Dutton, Jason L.
Format Journal Article
LanguageEnglish
Published England 09.11.2022
Subjects
Halogenation
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Summary:PhIBr 2 , first purported to exist over 100 years ago, has been subject of few reports due to its low stability. However, a recent publication proposes a reaction of PIFA (PhI(OC(O)-CF 3 ) 2 ) with TMSBr to form PhIBr 2 in situ and demonstrated its efficacy in aryl brominations. This report investigates this synthesis by replicating bromination reactions claiming to use in situ PhIBr 2 as described. The spectroscopical and computational results indicate formation of PhI and Br 2 where Br 2 is responsible for bromination and no supporting evidence for invoking PhIBr 2 as an intermediate is found.
ISSN:1477-0520
1477-0539
DOI:10.1039/D2OB01418A