Related Experiment Video
Updated: Mar 18, 2026
11:02
Synthesis and Catalytic Performance of Gold Intercalated in the Walls of Mesoporous Silica
Published on: July 9, 2015
10.6K
Gold Sulfinyl Mesoionic Carbenes: Synthesis, Structure, and Catalytic Activity
María Frutos1,2, Marta G Avello1,2, Alma Viso1,2
1Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas (CSIC) , Juan de la Cierva 3, 28006 Madrid, Spain.
Organic Letters
|July 13, 2016
Summary
New gold mesoionic carbene catalysts with chiral sulfoxide groups efficiently catalyze enyne cycloisomerization. The sulfoxide group enhances activity, while the N1-substituent controls regioselectivity in these important organic reactions.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Organic Synthesis
Background:
- Mesoionic carbenes (MICs) are versatile ligands in organometallic chemistry.
- Gold catalysis is crucial for various organic transformations, including cycloisomerizations.
- Controlling regioselectivity in catalytic reactions is a key challenge in synthetic chemistry.
Purpose of the Study:
- To synthesize novel gold mesoionic carbene complexes featuring a chiral sulfoxide group.
- To evaluate the catalytic efficiency of these new complexes in the cycloisomerization of enynes.
- To investigate the influence of the sulfoxide moiety and N1-substituent on catalytic activity and selectivity.
Main Methods:
- Synthesis of gold mesoionic carbene complexes with C4-chiral sulfoxide substituents.
- Catalytic testing in the cycloisomerization of various enyne substrates.
- Analysis of reaction products to determine yield, activity, and regioselectivity.
Main Results:
- The prepared gold mesoionic carbene catalysts demonstrated high efficiency in enyne cycloisomerization.
- The chiral sulfoxide group was found to be essential for the high catalytic activity.
- The N1-substituent on the mesoionic carbene ring effectively controlled the regioselectivity of the cycloisomerization.
Conclusions:
- Novel chiral gold mesoionic carbene complexes are effective catalysts for enyne cycloisomerization.
- The design of these catalysts allows for tuning of both activity and regioselectivity.
- This work provides new tools for stereoselective synthesis using gold catalysis.
