Improved synthesis of aryltriethoxysilanes via palladium(0)-catalyzed silylation of aryl iodides and bromides with triethoxysilane.
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.
Manoso
A S
AS
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
DeShong
P
P
D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis*
D006842:Hydrocarbons, Brominated; D006847:Hydrocarbons, Iodinated; D012821:Silanes; D010165:Palladium