Dimethylzinc-Initiated Radical Coupling of β-Bromostyrenes with Ethers and Amines

Amanda Birgitte Sølvhøj, Andreas Ahlburg, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A new coupling reaction has been developed in which β-bromostyrenes react with ethers and tertiary amines to introduce the styryl group in the α-position. The transformation is mediated by Me2Zn/O2 with 10 % MnCl2 and is believed to proceed by a radical addition-elimination mechanism. The ether and the amine are employed as solvent and the coupling takes place through the most stable α radical for unsymmetrical substrates. The products are obtained in moderate to good yields as the pure E isomers. The coupling can be achieved with a range of smaller cyclic and acyclic ethers/amines as well as various substituted β-bromostyrenes.
Original languageEnglish
JournalChemistry: A European Journal
Volume21
Issue number45
Pages (from-to)16272-16279
Number of pages8
ISSN0947-6539
DOIs
Publication statusPublished - 2015

Keywords

  • C-C coupling
  • C-H activation
  • Amines
  • Radical reactions
  • Synthetic methods

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