Scalable Total Synthesis of (−)-Triptonide: Serendipitous Discovery of a Visible-Light-Promoted Olefin Coupling Initiated by Metal-Catalyzed Hydrogen Atom Transfer (MHAT)
Xianhe Fang, Nan Zhang, Si‐Cong Chen, Tuoping Luo
Abstract
An efficient and scalable total synthesis of (-)-triptonide is accomplished based on a metal-catalyzed hydrogen atom transfer (MHAT)-initiated radical cyclization. During the optimization of the key step, we discovered that blue LEDs significantly promoted the efficiency of reaction initiated by Co(TPP)-catalyzed MHAT. Further exploration and optimization of this catalytic system led to development of a dehydrogenative MHAT-initiated Giese reaction.
Topics & Concepts
ChemistryCatalysisHydrogen atomOlefin fiberHydrogenMetalCombinatorial chemistryPhotochemistryAtom-transfer radical-polymerizationScalabilityAtom (system on chip)Organic chemistryPolymerizationPolymerDatabaseAlkylEmbedded systemComputer scienceCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions