Litcius/Paper detail

Photoinduced Palladium-Catalyzed Regio- and Chemoselective Elimination of Primary Alkyl Bromides: A Mild Route to Synthesize Unactivated Terminal Olefins

Sen Yang, Hao Hu, Ming Chen

2023Organic Letters15 citationsDOI

Abstract

Presented is a highly efficient method for visible-light-induced regio- and chemoselective elimination of alkyl halides yielding unactivated terminal olefins vital in organic synthesis. Achieved through ligand control, the reaction exhibits remarkable regioselectivity and suppresses undesired side reactions, particularly 1,5-hydrogen atom transfer (HAT). The process favors primary alkyl halides while preserving secondary and tertiary alkyl bromides, thereby enabling the incorporation of terminal olefins in complex molecules for late-stage functionalization.

Topics & Concepts

ChemistryAlkylRegioselectivityHalideCatalysisChemoselectivityPalladiumPrimary (astronomy)Ligand (biochemistry)Combinatorial chemistryMoleculeOrganic chemistryReceptorAstronomyPhysicsBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions