Indium-catalyzed radical reductions of organic halides with hydrosilanes.
Indium-catalyzed radical reductions of organic halides with hydrosilanes.
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DOI：
10.1021/jo061880o
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发表时间：
2007-02
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影响因子：
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通讯作者：
Katsukiyo Miura;Mitsuru Tomita;Yusuke Yamada;A. Hosomi
中科院分区：
文献类型：
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作者：
Katsukiyo Miura;Mitsuru Tomita;Yusuke Yamada;A. Hosomi
用In(OAc)3催化溴、碘烷烃与PhSiH3在70℃的四氢呋喃中反应，得到了高收率的脱卤烷烃。在Et3B和空气存在的情况下，30℃下还原过程顺利进行。当2,6-lutidine和空气作为添加剂时，In(OAc)3催化体系可以在EtOH中高效还原简单的官能化碘烷烃。用聚甲基氢硅氧烷（PMHS）催化还原卤代烷烃是有效的。这些催化还原可能涉及一种自由基链机制，其中铟或氢化镓作为实际的还原剂。
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.