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Synthesis 2008(12): 1911-1917
DOI: 10.1055/s-2008-1067082
DOI: 10.1055/s-2008-1067082
PAPER
© Georg Thieme Verlag Stuttgart · New York
Mild Copper(I) Iodide/β-Keto Ester Catalyzed Coupling Reactions of Styryl Bromides with Phenols, Thiophenols, and Imidazoles
Weitere Informationen
Received
14 December 2007
Publikationsdatum:
16. Mai 2008 (online)
Publikationsverlauf
Publikationsdatum:
16. Mai 2008 (online)
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Abstract
An efficient and mild vinylation of O-, S-, and N-nucleophiles is reported. Copper(I) iodide/ethyl 2-oxocyclohexanecarboxylate is used as the catalytic system. The protocol tolerates a broad range of functional groups on the substrates, and gives the corresponding aryl styryl ethers, aryl styryl sulfides, and N-styrylimidazoles in moderate to excellent yields as well as with good stereoselectivity.
Key words
β-keto esters - Ullmann coupling reaction - copper catalysis - vinylation
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