On the potential intermediacy of PhIBr2 as a brominating agent

PhIBr2, 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)-CF3)2) with TMSBr to form PhIBr2in situ and demonstrated its efficacy in aryl brominations. This report investigates thi...

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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 Cambridge Royal Society of Chemistry 09.11.2022
Subjects
Bromination
Chemical synthesis
Computer applications
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Summary:PhIBr2, 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)-CF3)2) with TMSBr to form PhIBr2in situ and demonstrated its efficacy in aryl brominations. This report investigates this synthesis by replicating bromination reactions claiming to use in situ PhIBr2 as described. The spectroscopical and computational results indicate formation of PhI and Br2 where Br2 is responsible for bromination and no supporting evidence for invoking PhIBr2 as an intermediate is found.
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d2ob01418a