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• W2328506604 abstract "Utilizing the aza-Wittig reaction involving the ylid 3,5-(CF3)2C6H3NPPh3 and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione, a highly fluorinated and electron-withdrawing β-diketiminate was obtained. Using strong bases, nBuLi, Ag2O, or TlOEt, the corresponding β-diketiminato-Li, -Ag, or -Tl chelated complexes were prepared. Subsequent in situ transmetalation with (Ru(η6-C6H6)Cl2)2 or (Ru(η6-p-cymene)Cl2)2 afforded the half-sandwich chloro-substituted Ru(II) β-diketimino complexes in high yield. The synthesis of the Lewis acidic catalysts featuring a vacant coordination site at the metal center was accomplished using [Na]BArF (BArF = tetrakis[3,5-bis(trifluoromethyl)phenyl]boron). These complexes are active for the Lewis acid catalyzed Diels–Alder reaction between α,β-unsaturated aldehydes, that is, methacrolein, acrolein, and dienes, that is, cyclopentadiene and 2,3-dimethyl-1,3-butadiene, with conversions in the range of 66–98% under mild conditions. Whereas the herein described catalysts generally promote exo selectivity of the [4 + 2] cycloaddition between methacrolein and cyclopentadiene, the reaction involving acrolein shows predominantly the formation of the endo adduct, similar to that observed for the noncatalyzed reaction. Importantly, the coordinatively unsaturated complexes demonstrate moderate Lewis acidity, which allows for the controlled reaction between methacrolein and 2,3-dimethyl-1,3-butadiene to 1,3,4-trimethyl-3-cyclohexene-1-carboxaldehyde without further isomerization to the bicyclic ketone, which is in contrast to strong Lewis acidic catalysts based on transition metals or main-group elements reported in the literature." @default.
• W2328506604 created "2016-06-24" @default.
• W2328506604 creator A5055785011 @default.
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• W2328506604 creator A5073727743 @default.
• W2328506604 creator A5078072008 @default.
• W2328506604 date "2011-09-29" @default.
• W2328506604 modified "2023-10-17" @default.
• W2328506604 title "Application of Electron-Withdrawing Coordinatively Unsaturated η⁶-Arene β-Diketiminato–Ruthenium Complexes in Lewis Acid Catalyzed Diels–Alder Reactions" @default.
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• W2328506604 doi "https://doi.org/10.1021/om200566a" @default.
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