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

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.