铟催化有机卤化物与硅烷的自由基还原反应。
Indium-catalyzed radical reductions of organic halides with hydrosilanes.
作者信息
Miura Katsukiyo, Tomita Mitsuru, Yamada Yusuke, Hosomi Akira
机构信息
Department of Chemistry, 21st Century COE, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
出版信息
J Org Chem. 2007 Feb 2;72(3):787-92. doi: 10.1021/jo061880o.
The In(OAc)3-catalyzed reaction of bromo- and iodoalkanes with PhSiH3 in THF at 70 degrees C gave dehalogenated alkanes in good to high yields. In the presence of Et3B and air, the reduction proceeded smoothly at 30 degrees C. When 2,6-lutidine and air were used as additives, the In(OAc)3-catalyzed system enabled an efficient reduction of simple and functionalized iodoalkanes in EtOH. Catalytic use of GaCl3 was found to be effective in the reduction of haloalkanes with poly(methylhydrosiloxane) (PMHS). These catalytic reductions probably involve a radical chain mechanism in which indium or gallium hydride species work as the actual reductants.
三乙酸铟催化溴代烷烃和碘代烷烃与苯基硅烷在四氢呋喃中于70℃反应，得到脱卤代烷烃，产率良好至高。在三乙基硼和空气存在下，还原反应在30℃顺利进行。当使用2,6-二甲基吡啶和空气作为添加剂时，三乙酸铟催化体系能够在乙醇中高效还原简单的和官能化的碘代烷烃。发现氯化镓的催化使用对于用聚甲基氢硅氧烷（PMHS）还原卤代烷烃是有效的。这些催化还原可能涉及自由基链机制，其中铟或镓氢化物物种作为实际的还原剂。
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