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Intramolecular Hydroarylation of Alkynes Catalyzed by Platinum or Gold: Mechanism and endo Selectivity
Abstract
The cyclization of differently substituted aryl alkynes with Pt II or Au I catalysts proceeds by endo‐dig pathways. When Ag I was used to generate reactive cationic Au I catalysts, 2 H‐chromenes dimerize to form cyclobutane derivatives by a Ag I‐catalyzed process. A DFT study on the cyclization mechanism shows a kinetic and thermodynamic preference for 6‐endo‐dig versus 5‐exo‐dig cyclizations in Pt II‐catalyzed processes. Calculations indicate that although Friedel–Crafts and the cyclopropanation processes via metal cyclopropyl carbenes show very similar activation energies, platinum cyclopropyl carbenes are the stationary points with the lowest energy.
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Highly Selective Gold-Catalyzed Arene Synthesis
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Cited by
Hashmi, A. S. K., & Hutchings, G. J. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200602454 · Cited by 3,423
Catalysis by Supported Gold Nanoparticles: Beyond Aerobic Oxidative Processes
Stratakis, M., & Garcia, H. (2012) · Chemical Reviews · doi:10.1021/cr3000785 · Cited by 803
Metadata
- Authors
- Nevado, C., & Echavarren, A. M.
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2005-01
- Volume
- 11
- Issue
- 10
- Pages
- 3155-3164
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W2100708161
- Cited by
- 309
- References
- 8
- FWCI
- 16.27
- Type
- journal article
- Language
- en
- Open access
- closed
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- Nevado, C., & Echavarren, A. M. (2005). Intramolecular Hydroarylation of Alkynes Catalyzed by Platinum or Gold: Mechanism and endo Selectivity. Chemistry – A European Journal. https://doi.org/10.1002/chem.200401069
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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