Palladium‐Catalyzed Cross‐Coupling between Alkylidenecyclopropanes and Boronic Acids

Author:

Rodiño Ricardo1,Mardones Fernando2,Paredes Krishna2,Jiménez Claudio A.2,Nelson Ronald3,Mascareñas Jose4,Lopez Fernando5,Verdugo Felipe2

Affiliation:

1. University of Santiago de Compostela SPAIN

2. Universidad de Concepción CHILE

3. Catholic University of the North CHILE

4. Universidad de Santiago SPAIN

5. CSIC SPAIN

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, such as has been proposed for other metal‐promoted hydrofunctionalizations of ACPs.

Publisher

Wiley

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