Pd-Catalyzed Multicomponent Cross-Coupling of Allyl Esters with Alkyl Bromides and Potassium Metabisulfite: Access to Allylic Sulfones
Kai‐Yi Zhang, Fang Long, Chuan‐Chong Peng, Jinhui Liu, Li‐Jun Wu
Abstract
A Pd-catalyzed multicomponent cross-coupling of allyl esters with alkyl bromides to synthesize allylic sulfones by using K 2 S 2 O 5 as a connector is first reported. The reaction displays a broad range of substrate generality along with excellent functional group compatibility and produces the products with high regioselectivity (only E). Furthermore, the biologically active molecules with a late-stage modification, including aspirin, menthol, borneol, and estrone, are also highly compatible with the multicomponent cross-coupling reaction. Mechanistic studies indicate that the process of SO 2 insertion into the C–Pd bond was involved in this transformation.
Topics & Concepts
ChemistryAllylic rearrangementAlkylCatalysisRegioselectivityReagentCoupling reactionFunctional groupCombinatorial chemistryMedicinal chemistryOrganic chemistryPolymerSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions