Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1324415 | Journal of Organometallic Chemistry | 2011 | 11 Pages |
Pd(OAc)2 was found to catalyze the direct arylation of some functionalized halothiophene derivatives allowing the synthesis in only one step of polyfunctionalized arylated thiophenes. In the presence of 2-acetyl-3-chlorothiophene, 2-acetyl-4-chlorothiophene, 2-acetyl-3-bromothiophene diethylacetal or 2-(4-bromothiophen-2-yl)-[1,3]dioxolane, and a variety of aryl bromides, the 5-arylation products were obtained in moderate to high yields employing only 0.5 mol% catalyst. On the other hand, the use of 2-formyl-3-chlorothiophene, 2-acetyl-3-bromothiophene or 2-formyl-3-bromothiophene gave disappointing results.
Graphical abstractPd(OAc)2 catalyzes the direct arylation of some formyl- or acetyl-halothiophenes. With several substrates, the integrity of the carbon–halide bond was maintained.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Catalyzed direct arylations of formyl- or acetyl-halothiophene derivatives. ► The integrity of the carbon–halide bond was maintained. ► A low loading of palladium catalyst was employed. ► Atom-economic access to arylated thiophenes.