Palladium‐Catalyzed Cross‐Coupling between Alkylidenecyclopropanes and Boronic Acids
Abstract The combination of a Pd(0) source and a phosphoramidite ligand promotes a formal allylic cross‐coupling between alkylidenecyclopropanes (ACPs) and boronic acids to yield synthetically appealing 1,1‐disubstituted alkenes. Remarkably, the reaction proceeds both under neutral and basic conditions, and works with both aryl‐ and alkenylboronic acids. DFT calculations suggest that the reaction entails a C−C activation/protonation mechanism instead of a hydropalladation pathway, which has been frequently proposed for other metal‐promoted hydrofunctionalizations of ACPs.
Authors
- Ricardo Rodiño (ORCID: https://orcid.org/0000-0002-3419-5294)
- Ronald Nelson (ORCID: https://orcid.org/0000-0001-7449-6334)
- José L. Mascareñas (ORCID: https://orcid.org/0000-0002-7789-700X)
- Felipe Verdugo (ORCID: https://orcid.org/0000-0002-2466-5643)
- Fernando López (ORCID: https://orcid.org/0000-0002-0235-6858)
- Claudio A. Jiménez (ORCID: https://orcid.org/0000-0002-2622-8308)
- Krishna Paredes
- Fernando Mardones
Institutions
- Consejo Superior de Investigaciones Científicas (ES)
- University of Concepción (CL)
- Universidade de Santiago de Compostela (ES)
- Universidad Católica del Norte (CL)
- Misión Biológica de Galicia (ES)
- Center for Research in Molecular Medicine and Chronic Diseases (ES)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-08-21
- DOI
- https://doi.org/10.1002/adsc.202400657
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Agencia Nacional de Investigación y Desarrollo
- European Regional Development Fund
- Agencia Estatal de Investigación