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Substrate Controlled Regioselective Bromination of Acylated Pyrroles Using Tetrabutylammonium Tribromide (TBABr3).

Shuang GaoTravis K BethelTayeb KakeshpourGrace E HubbellJames E JacksonJetze J Tepe
Published in: The Journal of organic chemistry (2018)
Electrophilic bromination of pyrroles bearing carbonyl substituents at C-2 typically results in a mixture of the 4- and 5-brominated species, generally favoring the 4-position. Herein, we describe a substrate-controlled regioselective bromination in which tetra-butyl ammonium tribromide (TBABr3) reacts with pyrrole-2-carboxamide substrates to yield the 5-brominated species as the predominant (up to >10:1) product.
Keyphrases
  • genetic diversity
  • ionic liquid
  • structural basis