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Issue 24, 2016
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Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins

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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.

Graphical abstract: Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins

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Publication details

The article was received on 01 Apr 2016, accepted on 06 May 2016 and first published on 09 May 2016


Article type: Communication
DOI: 10.1039/C6OB00692B
Citation: Org. Biomol. Chem., 2016,14, 5622-5626
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    Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins

    M. Galli, C. J. Fletcher, M. del Pozo and S. M. Goldup, Org. Biomol. Chem., 2016, 14, 5622
    DOI: 10.1039/C6OB00692B

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