Ruthenium‐Catalyzed C−C Coupling of Terminal Alkynes with Primary Alcohols or Aldehydes: α,β‐Acetylenic Ketones (Ynones) via Oxidative Alkynylation
Eliezer Ortiz, Madeline M. Evarts, Zachary H. Strong, Jonathan Z. Shezaf, Michael J. Krische
Abstract
The first metal-catalyzed oxidative alkynylations of primary alcohols or aldehydes to form α,β-acetylenic ketones (ynones) are described. Deuterium labelling studies corroborate a novel reaction mechanism in which alkyne hydroruthenation forms a transient vinylruthenium complex that deprotonates the terminal alkyne to form the active alkynylruthenium nucleophile.
Topics & Concepts
AlkyneChemistryCatalysisNucleophilePrimary (astronomy)AlkynylationRutheniumOxidative coupling of methaneOrganic chemistryAldehydeCoupling reactionMedicinal chemistryPhysicsAstronomyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCatalytic Cross-Coupling Reactions