Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 7, Pages 4508-4523Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02735
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- Syngene
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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%.
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.
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