title: Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins.
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.
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK. s.goldup@soton.ac.uk.
authors.forename: Marzia
authors.initials: M
authors.lastname: Galli
authors.forename: Catherine J
authors.initials: CJ
authors.lastname: Fletcher
authors.forename: Marc
authors.initials: M
authors.lastname: Del Pozo
authors.forename: Stephen M
authors.initials: SM
authors.lastname: Goldup