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Updated: May 6, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Gold-catalyzed rearrangements and beyond
Carla Obradors1, Antonio M Echavarren
1Institute of Chemical Research of Catalonia (ICIQ) , Av. Països Catalans 16, 43007 Tarragona, Spain.
Gold(I) catalysis enables efficient cycloisomerization of enynes, forming complex molecular architectures. This study reveals gold(I)-stabilized cationic intermediates, crucial for various carbon-carbon bond-forming reactions and natural product synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Electrophilic metal complexes, particularly gold(I), catalyze cycloisomerizations of enynes, a key carbon-carbon bond-forming reaction.
- These reactions offer a versatile route to construct complex molecular architectures under mild conditions from accessible starting materials.
- Understanding the intricate mechanisms of these transformations is crucial for further synthetic development.
Purpose of the Study:
- To elucidate the mechanistic pathways of gold(I)-catalyzed enyne cycloisomerizations and related reactions.
- To highlight the role of gold(I) in stabilizing cationic intermediates, specifically cyclopropyl gold(I) carbenes.
- To showcase the synthetic utility of these reactions in constructing complex molecules and natural products.
Main Methods:
- Investigation of gold(I)-catalyzed reactions involving enynes, alkynes, and alkenes.
- Analysis of reaction mechanisms through the lens of discrete cationic intermediates.
- Application of these methodologies in the stereoselective synthesis of natural products.
Main Results:
- Gold(I) activates alkynes, forming intermediates that readily react with nucleophiles, including alkenes, leading to cyclopropyl gold(I) carbene-like species.
- These intermediates can undergo skeletal rearrangements or react with external nucleophiles via stereospecific syn- or anti-additions.
- Cascade reactions initiated by nucleophilic attack on cyclopropyl gold(I) carbenes enable the formation of multiple bonds and complex structures, as demonstrated in natural product synthesis.
Conclusions:
- Gold(I) catalysis provides a powerful platform for diverse enyne transformations, proceeding through gold(I)-stabilized cationic intermediates.
- The cyclopropyl gold(I) carbene intermediate offers a valuable mechanistic concept for understanding and predicting reactivity.
- These gold(I)-catalyzed reactions are highly effective for the stereoselective synthesis of complex organic molecules, including natural products.
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