Palladium-Catalyzed Transfer Iodination from Aryl Iodides to Nonactivated C(<i>sp</i><sup>3</sup>)–H Bonds
Emilien Le Saux, Bill Morandi
Abstract
We report a new strategy for the catalytic iodination of nonactivated C( sp 3 )–H bonds. The method merges the concepts of shuttle and light-enabled palladium catalysis to employ aryl iodides as both hydrogen atom transfer reagents and iodine donors. A noncanonical Pd 0 /Pd I catalytic cycle is harnessed to transfer iodine from a C( sp 2 ) to a C( sp 3 )–H bond under mild conditions, which tolerate sensitive functional groups. This mechanism is also applied to implement a C( sp 3 )–H thiolation that exploits reversible steps of the system.
Topics & Concepts
ChemistryPalladiumHalogenationCatalysisArylMedicinal chemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions