Abstract
Renewable phenols have been investigated as nucleophiles for the addition to a cationic cyclohexadienyl iron carbonyl scaffold. Benign conditions compatible with solvents such as ethanol and water ...
Highlights
Biomass is becoming increasingly important as a renewable feedstock to provide the chemicals needed for our society.[1]
The carbon atoms adjacent to the diene are activated for hydride abstraction, resulting in the formation of a stable cationic iron carbonyl dienyl cation.[8,9]
While anilines have been widely shown to react as nucleophiles via selective C- or Naddition,[20−23] the analogous reactivity of phenols has not been examined to the same extent.[18,24]
Summary
Biomass is becoming increasingly important as a renewable feedstock to provide the chemicals needed for our society.[1]. Subsequent nucleophilic addition takes place stereoselectively, to the opposite face of the coordinated iron carbonyl moiety.[12,13] Other advantages of this methodology are the mild reaction conditions used, and the fact that the tailoring of reaction conditions for each class of nucleophile is generally not required Applications of this method include the synthesis of natural products, such as siculinine[14] and clausine K;15 antiviral compounds, such as oseltamivir phosphate (Tamiflu);[16,17] probes for infrared spectroscopy;[18] as well as parallel synthesis applications.[19] While anilines have been widely shown to react as nucleophiles via selective C- or Naddition,[20−23] the analogous reactivity of phenols has not been examined to the same extent.[18,24] Considering that phenols can potentially be sourced from lignin or other biomass sources, we have investigated their application as nucleophiles using the cationic iron carbonyl methodology.
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