Instantaneous SmI2-H2O-mediated reduction of dialkyl ketones induced by amines in THF

Instantaneous SmI2-H2O-mediated reduction of dialkyl ketones induced by amines in THF
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DOI:
10.1016/s0040-4039(02)01673-8
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发表时间:
2002-09-30
影响因子:
1.8
通讯作者:
Hilmersson, G
Hilmersson, G
中科院分区:
化学4区
文献类型:
--
作者:
Dahlén, A;Hilmersson, G

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用二碘化钐(2.5当量)将各种酮还原成相应的醇是瞬间的,即在不到10 S的时间内完成。在水存在下(6.25当量)和一种胺(5当量)在THF。到目前为止,这种混合物中酮的还原速度远远超过胺或水单独测定的速度。与没有质子源的还原相比,速率提高至少10万,或者比广泛使用的HMPA/酒精加速还原的速率至少快100倍。因此,这一新方法被认为是一种很好的替代有毒的HMPA/乙醇方法。(C)2002爱思唯尔科学有限公司。保留所有权利。
Reduction of various ketones to their corresponding alcohols is shown to be instantaneous, i.e. completed in less than 10 s, by samarium diiodide (2.5 equiv.) in the presence of water (6.25 equiv.) and an amine (5 equiv.) in THF. The rates of reduction of ketones in this mixture exceed by far the rates determined by an amine or water alone. Rate enhancement is at least 100 000 compared to the reduction without a proton source, or at least 100 times faster than the rate of the widely used HMPA/alcohol accelerated reductions. This new method is therefore suggested to be an excellent replacement of the toxic HMPA/alcohol method. (C) 2002 Elsevier Science Ltd. All rights reserved.