Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins

Marzia Galli, Catherine J. Fletcher, M. del Pozo Puig, Stephen M. Goldup

Research output: Contribution to journalArticleAcademicpeer-review

7 Citations (Scopus)
17 Downloads (Pure)

Abstract

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 & Biomolecular Chemistry
Volume14
DOIs
Publication statusPublished - 9 May 2016
Externally publishedYes

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