Work

Palladium‐Catalyzed Cross‐Coupling between Alkylidenecyclopropanes and Boronic Acids

Year: 2024

Type: article

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.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.202400657

Authors: Ricardo Rodiño, Fernando Mardones, Krishna Paredes, Claudio A. Jiménez, Ronald Nelson, José L. Mascareñas, Fernando López, Felipe Verdugo

Institutions: Universidade de Santiago de Compostela, Centro Singular de Investigación en Química Biológica y Materiales Moleculares, University of Concepción, Universidad Católica del Norte, Consejo Superior de Investigaciones Científicas, Misión Biológica de Galicia

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Agencia Nacional de Investigación y Desarrollo, European Regional Development Fund, Agencia Estatal de Investigación

Awards: G1175115578, CATALYTIC [3+2] CYCLOADDITIONS BETWEEN INDOLES AND DONOR-ACCEPTOR CYCLOPROPANES AND AZIRIDINES WITHOUT PRECIOUS METALS, G1622782223, G1888088267, G2262748287, G2541661227, G300979063, G34346518, G3480869486, G410571670, G425668148, G451917667, G5080475149, G5539308778, G5967599077, G7084143925, ENANTIOSELECTIVE SYNTHESIS OF FUSED HETEROCYCLES USING VINYLCYCLOPROPANES AND FIRST-ROW TRANSITION METAL CATALYSTS, G929308097

OpenAlex ID: W4401790659

FWCI: 0.282

Cites: 41

Cited by: 2

Related to: 10