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Updated: Jun 21, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Selective C-S bond formation via Fe-catalyzed allylic substitution
Markus Jegelka1, Bernd Plietker
1Institut für Organische Chemie, FB Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany.
Researchers developed a new iron-catalyzed method for selective C-S bond formation. This process efficiently creates chiral aryl allyl sulfones, offering a valuable tool for organic synthesis.
Area of Science:
- Organic Chemistry
- Organometallic Chemistry
- Catalysis
Background:
- Selective carbon-sulfur (C-S) bond formation is a critical area in organic synthesis.
- Sulfur's diverse oxygenation states offer varied chemical properties, yet C-S bond formation lags behind C-O and C-N bond formation in research focus.
- Transition metal catalysis is increasingly important for selective bond constructions.
Purpose of the Study:
- To develop a regioselective catalytic method for C-S bond formation.
- To explore the utility of iron catalysis in allylic sulfonation reactions.
- To synthesize chiral aryl allyl sulfones with high efficiency and selectivity.
Main Methods:
- Utilized an iron complex as a catalyst for allylic sulfonation.
- Employed regioselective reaction conditions to control the site of C-S bond formation.
- Investigated the preparation of various aryl allyl sulfones.
Main Results:
- Achieved regioselective iron-catalyzed allylic sulfonation.
- Successfully synthesized a range of chiral aryl allyl sulfones.
- Obtained good to excellent yields for the target sulfone products.
Conclusions:
- Demonstrated a novel and efficient Fe-catalyzed approach for allylic sulfonation.
- Highlighted the potential of iron catalysis in selective C-S bond formation.
- Provided a valuable method for accessing chiral aryl allyl sulfones.
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Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

