Indium-Catalyzed Radical Reductions of Organic Halides with Hydrosilanes

详细信息    查看全文

• 作者：Katsukiyo Miura ; Mitsuru Tomita ; Yusuke Yamada ; Akira Hosomi
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：February 2, 2007
• 年：2007
• 卷：72
• 期：3
• 页码：787 - 792
• 全文大小：118K
• 年卷期：v.72,no.3(February 2, 2007)
• ISSN：1520-6904

文摘

The In(OAc)₃-catalyzed reaction of bromo- and iodoalkanes with PhSiH₃ in THF at 70 C gavedehalogenated alkanes in good to high yields. In the presence of Et₃B and air, the reduction proceededsmoothly at 30 C. When 2,6-lutidine and air were used as additives, the In(OAc)₃-catalyzed systemenabled an efficient reduction of simple and functionalized iodoalkanes in EtOH. Catalytic use of GaCl₃was found to be effective in the reduction of haloalkanes with poly(methylhydrosiloxane) (PMHS). Thesecatalytic reductions probably involve a radical chain mechanism in which indium or gallium hydridespecies work as the actual reductants.