Novel Water-Soluble Organosilane Compounds as a Radical Reducing Agent in Aqueous Media

The development of novel water-soluble organosilane compounds and their application to radical reactions in water medium have been studied. A series of novel organosilane compounds having hydrophilic groups, such as an ether group and a hydroxy group in the side chain to bear hydrophilicity, were synthesized by the reaction of trichlorosilane or tetrachlorosilane and Grignard reagents. The reactivities of these organosilane compounds were studied in the radical reduction of 2-bromoethyl phenyl ether in ethanol in the presence of triethylborane under aerobic conditions. The results showed that diarylsilane was the most effective among them. The radical reduction of alkyl and aryl halides with diarylsilane was applied to a reaction in aqueous media, which gave the corresponding reduction product in good yields. Thus, the present organosilanes are very useful for the reduction of water-soluble substrates, such as halo sugars in water.