Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene

Journal of the Brazilian Chemical Society

Kamal M. Dawood¹  Hamdi M. Hassaneen¹  Hyam A. Abdelhadi¹  Mohamed S. M. Ahmed¹  Mohamed A.-m. Mohamed¹ 

[1] ,Cairo University Faculty of Science Chemistry DepartmentGiza,Egypt

关键词: arylacetylenes;    cross-coupling;    catalysis;    palladium;    aqueous media;   

DOI  :  10.5935/0103-5053.20140163

来源: SciELO

【 摘 要 】

Sonogashira coupling of trimethylsilylacetylene with 4-alkyloxy-1-iodobenzenes gave 2-(4-(alkyloxy)phenyl)ethynyltrimethylsilanes which undergo deprotection via removal of TMS-group using tetrabutylammonium fluoride (TBAF) in THF at room temperature to afford the corresponding terminal 2-(4-(alkyloxy)phenyl)acetylenes. Regiocontrolled Sonogashira cross-coupling of 1,3,5-tribromobenzene with the terminal arylacetylenes in aqueous medium resulted in the formation of mono-, di- and tri-alkynylated benzene derivatives in moderate to good yields. Factors affecting the regioselective alkynylation were also examined.

【 授权许可】

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