Synthesis of Stereodefined Enones from the Cross-Electrophile Coupling of Activated Acrylic Acids with Alkyl Bromides

We report a one-pot synthesis of (E)-trisubstituted enones from acrylic acids through the in situ generation of a 2-pyridyl ester and subsequent cross-electrophile coupling with a nickel catalyst under reducing conditions. The scope of trisubstituted enones is broad and compatible with functionality that can be challenging in established olefination techniques. We highlight conditions necessary to suppress undesired side reactions from the α,β-unsaturated carbonyl and improve cross-electrophile coupling approaches to prepare enones.