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Dimethylzinc‐Initiated Radical Coupling of β‐Bromostyrenes with Ethers and Amines
Author(s) -
Sølvhøj Amanda,
Ahlburg Andreas,
Madsen Robert
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502429
Subject(s) - chemistry , dimethylzinc , amine gas treating , ether , solvent , coupling (piping) , coupling reaction , organic chemistry , transformation (genetics) , medicinal chemistry , photochemistry , catalysis , materials science , biochemistry , gene , metallurgy
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 Me 2 Zn/O 2 with 10 % MnCl 2 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.