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. image