2007
DOI: 10.1002/ange.200702571
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Mechanistic Studies of Proton‐Donor Coordination to Samarium Diiodide

Abstract: Alcohols, glycols, and glymes are commonly used as additives in numerous reductions and reductive coupling reactions of samarium diiodide (SmI 2 ). [1,2] Typically alcohols and glycols are used as proton donor sources, whereas glymes are used as coordinating additives. All of these additives have been shown to exert an influence on the regiochemical [3,4] and stereochemical [5,6] outcomes of numerous SmI 2 -mediated reactions. The seminal work of Hoz et al. demonstrated that the interplay between proton-donor … Show more

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Cited by 15 publications
(2 citation statements)
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“…Der aktivierende Einfluss chelatisierender Alkohole und Ether auf das Einelektronen‐Reduktionsreagenz SmI2 beruht darauf, dass gering konzentrierte Additive Koordinationsstellen für das Substrat schaffen 71. Das Sättigen des Metalldikations mit Additiv führt hingegen zu einer Deaktivierung.…”
Section: Metallorganik I: Strukturen Und Mechanismenunclassified
“…Der aktivierende Einfluss chelatisierender Alkohole und Ether auf das Einelektronen‐Reduktionsreagenz SmI2 beruht darauf, dass gering konzentrierte Additive Koordinationsstellen für das Substrat schaffen 71. Das Sättigen des Metalldikations mit Additiv führt hingegen zu einer Deaktivierung.…”
Section: Metallorganik I: Strukturen Und Mechanismenunclassified
“…The reduction of (2 R )- 7 was examined using different alcohols in place of water (Table ), since the nature of these additives can influence the mechanism and outcome of reactions with SmI 2 . Chiral amino diol 14 along with ( R )- and ( S )-BINOL were also included, which have been reported for enantioselective Sm­(II)-based transformations. Replacement of water in all cases caused a significant drop in conversion even with extended reaction times (the mass balance in all cases was unreacted starting material) and no practical improvement to d.r.…”
mentioning
confidence: 99%