D. Procter, R. Flowers, T. Skrydstrup
Nov 10, 2009
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Abstract
Samarium diiodide (SmI2) is a one-electron reducing agent that is employed extensively in organic synthesis to bring about a wide variety of transformations. Its ability to mediate both radical and anionic processes as well as cascade reactions involving both types of reactivity is central to its status as one of the most versatile reducing agents available to the organic chemist. This article reviews the use of SmI2 in organic chemistry, including the preparation of the reagent, the influence of additives, and mechanistic considerations. A discussion of the varied functional group transformations effected by SmI2 is supplemented by examples chosen from the literature to highlight synthetically valuable processes and emphasize the scope of the reagent. Finally, a wide range of carbon–carbon bond-forming processes mediated by SmI2 is presented, including pinacol couplings, carbonyl–alkene couplings, radical alkene–alkyne additions, Barbier and Grignard reactions, Reformatsky and aldol-type reactions, as well as sequential carbon–carbon bond-forming reactions. Keywords: samarium; electron transfer; reduction; radicals; anions; cyclization; cascade