Journal article
Dimethylzinc-Initiated Radical Coupling of β-Bromostyrenes with Ethers and Amines
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.
Language: | English |
---|---|
Publisher: | WILEY‐VCH Verlag |
Year: | 2015 |
Pages: | 16272-16279 |
ISSN: | 15213765 and 09476539 |
Types: | Journal article |
DOI: | 10.1002/chem.201502429 |
ORCIDs: | Madsen, Robert |
CC coupling CH activation amines radical reactions synthetic methods