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Reversing the Role of the Metal−Oxygen π-Bond. Chemoselective Catalytic Reductions with a Rhenium(V)-Dioxo Complex

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journal contribution
posted on 15.03.2003, 00:00 authored by Joshua J. Kennedy-Smith, Kristine A. Nolin, Haluna P. Gunterman, F. Dean Toste
The metal−oxygen bond plays a critical role in some of the most important biological and synthetic reactions. However, the majority of these processes result in the oxidation of the target organic substrate; applications of this class of metal complexes to other organic transformations are extremely rare. In this paper, we report a new type of catalytic process in which complexes with metal−oxygen multiple bonds are used as reductants rather than oxidants. The overall reaction provides a highly chemoselective reduction/protection of carbonyl groups. In addition to providing a new way of catalyzing organic reactions, these catalysts can be used in the presence of a wide range of other functional groups such as amino, cyano, nitro, aryl halo, ester, and alkene; unlike many of their late metal relatives, they are inexpensive as well as air and moisture tolerant.