Orchestrating aβ-Hydride Elimination Pathway in Palladium(II)-Catalyzed Arylation/Alkenylation of Cyclopropanols UsingOrganoboron Reagents

The scope of chemoselective beta-hydride elimination in the context of arylation/alkenylation of homoenolates fromcyclopropanol precursors using organoboronic reagents as transmetalation coupling partners was examined. The reactionoptimization paradigm revealed a simple ligand-free Pd(II) catalytic system to be most efficient under open air conditions. Thepreparative scope, which was investigated with 48 examples, supported the applicability of this reaction to a wide range of substratestolerating a variety of functional groups while delivering beta-substituted enone and dienone derivatives in 62-95% yields.

Automated summary

The scope of chemoselective beta-hydride elimination in the context of arylation/alkenylation of homoenolates from cyclopropanol precursors using organoboronic reagents as transmetalation coupling partners was examined. The reaction optimization paradigm revealed a simple ligand-free Pd(II) catalytic system to be most efficient under open air conditions. The preparative scope, which was investigated with 48 examples, supported the applicability of this reaction to a wide range of substrates tolerating a variety of functional groups while delivering beta-substituted enone and dienone derivatives in yields of 62-95%.