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Recent advances in the chemoselective reduction of functional groups mediated by samarium(ii) iodide: a single electron transfer approach

2013; Royal Society of Chemistry; Volume: 42; Issue: 23 Linguagem: Inglês

10.1039/c3cs60223k

1460-4744

Michal Szostak, Malcolm Spain, David J. Procter,

Catalytic C–H Functionalization Methods

Recently, samarium(II) iodide reductants have emerged as powerful single electron donors for the highly chemoselective reduction of common functional groups. Complete control of the product formation can be achieved on the basis of a judicious choice of a Sm(II) complex/proton donor couple, even in the presence of extremely sensitive functionalities (iodides, aldehydes). In most cases, the reductions are governed by thermodynamic control of the first electron transfer, which opens up new prospects for unprecedented transformations via radical intermediates under mild regio-, chemo- and diastereoselective conditions that are fully orthogonal to hydrogenation or metal-hydride mediated processes.