Access to Amino Lactones through Palladium-Catalyzed Oxyamination with Aromatic Amines as the Nitrogen Source
Chao Liu, Jiahao Wu, Xiangwen Tan, Jinhui Zhang, Wanqing Wu, Huanfeng Jiang
Abstract
Although the synthesis of amino lactones with various nitrogen sources has achieved great success, variants focused on aromatic amine counterparts still remain elusive. Herein, we communicate the intermolecular oxyamination reaction of aromatic amines and unactivated alkenyl carbonyl compounds under palladium catalysis. In the reaction, both primary and second aromatic amines yield the corresponding β-arylamino-γ-lactones efficiently. A key step in this process involves a Pd II /Pd IV catalytic cycle incorporating a 1,2-(C–N)/(C–O) dyotropic rearrangement. This reaction demonstrates mild reaction conditions and good functional group compatibility.
Topics & Concepts
CatalysisChemistryPalladiumAmine gas treatingYield (engineering)Intermolecular forceNitrogenCatalytic cycleOrganic chemistryPrimary (astronomy)Reaction conditionsSynergistic catalysisFunctional groupCombinatorial chemistryMoleculeMaterials scienceMetallurgyPhysicsAstronomyPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsChemical Synthesis and Analysis