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

✍ Scribed by Anders Dahlén; Göran Hilmersson

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
142 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

Selective reduction of carboncarbon dou
Selective reduction of carboncarbon double and triple bonds in conjugated olefins mediated by SmI2/H2O/amine in THF
✍ Anders Dahlén; Göran Hilmersson 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 137 KB

Conjugated double and triple bonds are reduced into alkenes using non-hazardous SmI 2 /H 2 O/amine mixtures as reducing agents in THF. Isolated alkenes are not reduced during these reductions. All the reactions studied are quantitative and are completed in less than five minutes.