Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins

Marzia Galli, Catherine J. Fletcher, Marc Del Pozo, Stephen M. Goldup*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)


To improve access to a key synthetic intermediate we targeted a direct hydrobromination-Negishi route. Unsurprisingly, the anti-Markovnikov addition of HBr to estragole in the presence of AIBN proved successful. However, even in the absence of an added initiator, anti-Markovnikov addition was observed. Re-examination of early reports revealed that selective Markovnikov addition, often simply termed "normal" addition, is not always observed with HBr unless air is excluded, leading to the rediscovery of a reproducible and scalable initiator-free protocol.

Original languageEnglish
Pages (from-to)5622-5626
Number of pages5
JournalOrganic and Biomolecular Chemistry
Issue number24
Publication statusPublished - 2016

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2016.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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