Highly Regioselective Copper‐Catalyzed Transfer Hydrodeuteration of Unactivated Terminal Alkenes
Albert Reyes, Emanuel Rivera Torres, Zoua Pa Vang, Joseph R. Clark
Abstract
Catalytic transfer hydrodeuteration of unactivated alkenes is challenging because of the requirement that chemically similar hydrogen and deuterium undergo selective insertion across a π-bond. We now report a highly regioselective catalytic transfer hydrodeuteration of unactivated terminal alkenes across a variety of heteroatom- or heterocycle-containing substrates. The base-metal-catalyzed reaction is also demonstrated on two complex natural products. Reaction studies indicate modular conditions that can also be extended to perform either an alkene transfer hydrogenation or transfer deuteration.
Topics & Concepts
RegioselectivityCatalysisAlkeneChemistryTransfer hydrogenationCombinatorial chemistryHeteroatomOrganic chemistryCopperRing (chemistry)RutheniumChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisAdvanced Synthetic Organic Chemistry