期刊
SYNTHESIS-STUTTGART
卷 47, 期 21, 页码 3354-3362出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1378733
关键词
aryl halides; catalysis; C-H activation; benzo[b]thiophenes; palladium
资金
- Centre National de la Recherche Scientifique
- Rennes Metropole
- UTIQUE
Phosphine-free palladium(II) acetate catalyst was found to promote the direct 2-arylation of 3-bromobenzo[b]thiophene without cleavage of the benzothienyl carbon-bromine bond, allowing the synthesis of 2-aryl-3-bromobenzo[b]thiophenes in only one step. The best results were generally obtained using a low loading of the palladium catalyst (0.5 mol%), quite low reaction temperatures (80-120 degrees C) and short reaction times (0.5-2 h). The reaction proceeds with electron-deficient para-, meta- and ortho-substituted aryl bromides and also with heteroaryl bromides. The benzothienyl carbon-bromine bond has been profitably employed for further palladium-catalysed functionalisations. This strategy allows the straightforward synthesis of 2,3-di(hetero)arylated benzo[b] thiophenes with two different (hetero) aryl units via sequential catalytic arylations.
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