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 language | English |
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Journal | Chemistry - A European Journal |
Volume | 21 |
Issue number | 45 |
Pages (from-to) | 16272-16279 |
Number of pages | 8 |
ISSN | 0947-6539 |
DOIs | |
Publication status | Published - 2015 |
Keywords
- C-C coupling
- C-H activation
- Amines
- Radical reactions
- Synthetic methods