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Updated: Jul 19, 2025
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Synthesis and Catalytic Performance of Gold Intercalated in the Walls of Mesoporous Silica
Published on: July 9, 2015
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Hydrogen-Bonded Matched Ion Pair Gold(I) Catalysis.
Àlex Martí1,2, Gala Ogalla1,2, Antonio M Echavarren1,2
1Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology (BIST), Av. Països Catalans 16, 43007 Tarragona, Spain.
ACS Catalysis
|August 10, 2023
Summary
This study introduces a novel gold(I) catalysis method for enantioselective reactions using 1,6-enynes. The approach achieves high enantiocontrol through a matched ion pair system stabilized by hydrogen bonding.
Area of Science:
- Organic Chemistry
- Catalysis
- Asymmetric Synthesis
Background:
- 1,6-enynes are versatile synthetic intermediates.
- Achieving high enantioselectivity in reactions involving 1,6-enynes remains a challenge.
- Gold(I) catalysis offers promising pathways for complex organic transformations.
Purpose of the Study:
- To develop a novel enantioselective reaction of 1,6-enynes with various nucleophiles.
- To investigate the efficacy of a matched ion pair gold(I) catalysis system.
- To achieve high levels of enantiocontrol in these transformations.
Main Methods:
- Utilized a matched ion pair gold(I) catalysis system.
- Employed a chiral gold(I) cation and anion linked via hydrogen bonding through a urea group.
- Investigated reactions with O-, N-, and C-nucleophiles.
Main Results:
- Developed an enantioselective reaction for 1,6-enynes with O-, N-, and C-nucleophiles.
- Achieved very high enantioselectivity, with enantiomeric ratios (er) up to >99:1.
- Demonstrated a broad substrate scope for the developed methodology.
Conclusions:
- The matched ion pair gold(I) catalysis system effectively promotes enantioselective reactions of 1,6-enynes.
- Hydrogen bonding through a urea group is crucial for stabilizing the chiral ion pair and enhancing enantiocontrol.
- DFT studies confirmed the role of the H-bond donor in anchoring the ion pair and facilitating noncovalent interactions.
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