Improved synthesis of aryltriethoxysilanes via palladium(0)-catalyzed silylation of aryl iodides and bromides with triethoxysilane. |
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| Authors: | A S Manoso P DeShong |
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| Affiliation: | Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA. |
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| Abstract: | The scope of the palladium-catalyzed silylation of aryl halides with triethoxysilane has been expanded to include aryl bromides. A more general Pd(0) catalyst/ligand system has been developed that activates bromides and iodides: palladium(0) dibenzylideneacetone (Pd(dba)(2)) is activated with 2-(di-tert-butylphosphino)biphenyl (Buchwald's ligand) (1:2 mol ratio of Pd/phosphine). Electron-rich para- and meta-substituted aryl halides (including unprotected aniline and phenol derivatives) undergo silylation to form the corresponding aryltriethoxysilane in fair to excellent yield; however, ortho-substituted aryl halides failed to be silylated. |
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