Sodium Halides-Promoted S—Si Bond Activation and Its Application in the Synthesis of Unsymmetrical Thioethers
Unlike the conventional methods that require the use of fluoride salts for activation of the E—Si bonds of organo-silicon compounds by forming the strong Si—F bond,simple inorganic salt NaBr even the table salt NaCl could be used to effectively activate the S—Si bond through formation of the relatively weaker Si—X(X=Br,Cl)bonds.Employing this method,inorganic sodium halides can be used to promote the reaction of thiosilanes with non-fluorine alkyl halides,producing unsymmetrical alkyl thioethers under base-free neutral conditions.The reaction produced silyl halides TMSX as byproduct,which could be recovered.This method could also be extended to non-fluorine heteroaryl halides and electron-deficient aryl halides for the synthesis of heteroaryl and electron-deficient aryl thioethers,revealing the relatively broad substrate scope of the method.
thiosilanesS—Si bond activationsodium halidesunsymmetrical thioethers
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