The effect of lithium bromide and lithium chloride on the reactivity of SmI2 in THF

Fuchs, James R.; Mitchell, Michael; Shabangi, Masangu; Flowers, Robert A.

doi:10.1016/s0040-4039(97)10222-2

Cited by 98 publications

(53 citation statements)

References 10 publications

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“…Moreover, the Ellman group employed SmBr 2 generated in situ from SmI 2 and LiBr. [14] Therefore, it is quite likely that the lithium cation present in solution played a significant role in providing a highly ordered transition state in the reported coupling. This hypothesis is supported by the recent report by Gilles and Py, who determined that the lithium cation is required to obtain high levels of diastereoselectivity in a SmBr 2 -mediated cross-coupling of nitrones with b-silyla,b-unsaturated esters.…”

Section: Samarium(ii) Bromidementioning

confidence: 92%

“…(1)]. [14] Flowers and co-workers have investigated the use of SmBr 2 in C À C bond-forming reactions of alkyl halides and carbonyl compounds, and observed complete selectivity for pinacol coupling in the presence of reactive alkyl iodides (Scheme 3). [10] With SmBr 2 as a reductant, complete selectivity for pinacol coupling in the presence of reactive alkyl iodides was observed.…”

Section: Samarium(ii) Bromidementioning

confidence: 99%

“…(1)]. [14] A recent study by Matsukawa et al suggests, rather surprisingly, that this reagent can also be prepared from SmCl 3 and Sm metal in water. [23] SmCl 2 is an excellent promoter of challenging electron-transfer reactions.…”

Section: Samarium(ii) Chloridementioning

confidence: 99%

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Beyond Samarium Diiodide: Vistas in Reductive Chemistry Mediated by Lanthanides(II)

2012

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Reactions proceeding through open-shell, single-electron pathways offer attractive alternative outcomes to those proceeding through closed-shell, two-electron mechanisms. In this context, samarium diiodide (SmI(2)) has emerged as one of the most important and convenient-to-use electron-transfer reagents available in the laboratory. Recently, significant progress has been made in the reductive chemistry of other divalent lanthanides which for many years had been considered too reactive to be of value to synthetic chemists. Herein, we illustrate how new samarium(II) complexes and nonclassical lanthanide(II) reagents are changing the landscape of modern reductive chemistry.

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Section: Samarium(ii) Bromidementioning

confidence: 92%

Section: Samarium(ii) Bromidementioning

confidence: 99%

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Beyond Samarium Diiodide: Vistas in Reductive Chemistry Mediated by Lanthanides(II)

2012

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“…(1)]. [14] Flowers und Mitarbeiter erforschten die Verwendung von SmBr 2 im Rahmen von Reaktionen von Alkylhalogeniden mit Carbonylverbindungen unter C-C-Kupplung und beobachteten dabei vollständige Selektivität für die Pinakolkupplung in Gegenwart reaktiver Alkyliodide (Schema 3). [10] Mit [20] Enantiomerenreine 1,3-Diole sind nützliche Bausteine für die Naturstoffsynthese.…”

Section: Samarium(ii)-bromidunclassified

“…(1)]. [14] Eine Untersuchung von Matsukawa et al lässt darauf schließen, dass dieses Reagens auch aus SmCl 3 und Sm-Metall in Wasser hergestellt werden kann, was eher überraschend ist. [23] Bei SmCl 2 handelt es sich um einen hervorragenden Promotor für schwierige Elektronentransferreaktionen.…”

Section: Samarium(ii)-chloridunclassified

Jenseits von Samariumdiiodid: Perspektiven für Lanthanoid(II)‐vermittelte Reduktionen

Szostak

Procter

2012

Angewandte Chemie

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Reaktionen, die über offenschalige Einelektronenmechanismen ablaufen, führen zu interessanten alternativen Resultaten gegenüber solchen Reaktionen, die Zweielektronenmechanismen mit geschlossenen Schalen gehorchen. In diesem Zusammenhang entwickelte sich Samariumdiiodid zu einem der wichtigsten Elektronentransferreagentien. In letzter Zeit wurde ein signifikanter Fortschritt auf dem Gebiet der reduktiven Chemie anderer zweiwertiger Lanthanoide erzielt, die viele Jahre lang als zu reaktiv erachtet worden waren, um von Nutzen für Synthesechemiker zu sein. Wir beschreiben hier, wie neue Samarium(II)‐Komplexe und nichtklassische Lanthanoid(II)‐Reagentien die moderne reduktive Chemie verändern.

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Ligand Effects on the Diastereoselectivities of Samarium Diiodide Promoted Pinacol Coupling

et al. 1999

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The samarium diiodide pinacol coupling of benzaldehyde and cyclohexanecarboxaldehyde in the presence of a variety of polyethylene glycols, including derivatives containing carbohydrates has been studied. Whereas such complexing agents allow for the formation of 1,2‐diols, in the case of benzaldehyde the erythro‐isomer predominates with diastereoselectivities of up to 7:1, while with cyclohexanecarboxaldehyde a stereoselectivity of up to 10:1 was observed but in favor of the threo‐isomer. This divergence in the stereoselectivity of these two aldehydes suggests the presence of two different mechanisms occurring in these pinacol coupling reactions.

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The effect of lithium bromide and lithium chloride on the reactivity of SmI2 in THF

Cited by 98 publications

References 10 publications

Beyond Samarium Diiodide: Vistas in Reductive Chemistry Mediated by Lanthanides(II)

Beyond Samarium Diiodide: Vistas in Reductive Chemistry Mediated by Lanthanides(II)

Jenseits von Samariumdiiodid: Perspektiven für Lanthanoid(II)‐vermittelte Reduktionen

Ligand Effects on the Diastereoselectivities of Samarium Diiodide Promoted Pinacol Coupling

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