Recent advances in the iron-catalyzed C-C bond formation via polar reactions of alcohols with carbon-centered nucleophiles

Shang, Xiaojie; Liu, Zhong‐quan

doi:10.1007/s11434-012-5123-1

Cited by 10 publications

(3 citation statements)

References 45 publications

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“…However, until 2004, and thus within the coverage of the review by Bolm, only a few examples of iron-catalyzed nucleophilic substitutions had been reported . After 2004, these transformations, and in particular allylation reactions, have experienced a rapid development and were summarized in a number of reviews, highlight articles, and accounts. ,,,− …”

Section: Substitution Reactionsmentioning

confidence: 99%

“…In addition, Jana et al also introduced cinnamyl alcohol as a representative of an allylic alcohol to alkylate acetylacetone in 58% yield (Scheme , eq c). A brief summary of the iron-catalyzed substitution of alcohols by carbon-centered nucleophiles has been provided more recently …”

Section: Substitution Reactionsmentioning

confidence: 99%

“…A brief summary of the iron-catalyzed substitution of alcohols by carboncentered nucleophiles has been provided more recently. 49 García and Moriel described a method for the benzylation of 1,3-dicarbonyl compounds by benzylic alcohols (cf. Scheme 2) using iron-containing ionic liquids on mesoporous carbon supports as catalyst.…”

Section: Introductionmentioning

confidence: 99%

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Iron Catalysis in Organic Synthesis

2015

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Section: Substitution Reactionsmentioning

confidence: 99%

Section: Substitution Reactionsmentioning

confidence: 99%

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Iron Catalysis in Organic Synthesis

2015

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Base‐Free Non‐Noble‐Metal‐Catalyzed Hydrogen Generation from Formic Acid: Scope and Mechanistic Insights

Mellmann

Barsch

Bauer

et al. 2014

Chemistry A European J

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The iron-catalyzed dehydrogenation of formic acid has been studied both experimentally and mechanistically. The most active catalysts were generated in situ from cationic Fe(II) /Fe(III) precursors and tris[2-(diphenylphosphino)ethyl]phosphine (1, PP3 ). In contrast to most known noble-metal catalysts used for this transformation, no additional base was necessary. The activity of the iron catalyst depended highly on the solvent used, the presence of halide ions, the water content, and the ligand-to-metal ratio. The optimal catalytic performance was achieved by using [FeH(PP3 )]BF4 /PP3 in propylene carbonate in the presence of traces of water. With the exception of fluoride, the presence of halide ions in solution inhibited the catalytic activity. IR, Raman, UV/Vis, and EXAFS/XANES analyses gave detailed insights into the mechanism of hydrogen generation from formic acid at low temperature, supported by DFT calculations. In situ transmission FTIR measurements revealed the formation of an active iron formate species by the band observed at 1543 cm(-1) , which could be correlated with the evolution of gas. This active species was deactivated in the presence of chloride ions due to the formation of a chloro species (UV/Vis, Raman, IR, and XAS). In addition, XAS measurements demonstrated the importance of the solvent for the coordination of the PP3 ligand.

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