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Communication | Regular issue | Vol 31, No. 2, 1990, pp.219-221
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5268
Reaction of Aryl Halides with (Z)-1-Ethoxy-2-tributylstannylethene: A Versatile Method for the Introduction of 2-Ethoxyethenyl Group into Aromatic Nuclei

Takao Sakamoto, Yoshinori Kondo, Akito Yasuharu, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The reaction of 4-substituted bromobenzenes, except for 4-bromophenol and 4-bromoaniline, with (Z)-1-ethoxy-2-tributylstannylethene is well prompted by the catalytic action of dichlorobis(triphenylphosphine)palladium in dimethylformamide in the presence of tetraethylammonium chloride to give (Z)-1-ethoxy-2-(4-substituted phenyl)ethene. The method is also useful for the introduction of a 2-ethoxyethenyl moiety into heteroaromatic ring s such as pyridine, thiophene, indole.