Ruthenium-Catalyzed Chemoselective N–H Bond Insertion Reactions of 2-Pyridones/7-Azaindoles with Sulfoxonium Ylides
Xiaofeng Liu, Ying Shao, Jiangtao Sun
Abstract
A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, affording N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to achieve this unprecedented N–H rather than O–H insertion reaction is the use of CpRu(PPh3)2Cl as the catalyst and sulfoxonium ylides as the alkylation reagents. Moreover, this protocol is also amenable to 7-azaindoles by slightly varying the reaction conditions. Furthermore, sulfonium ylides are also suitable alkylation reagents, providing the N-alkylated 2-pyridones in good selectivity.
Topics & Concepts
ChemistrySulfoniumAlkylationReagentCatalysisRutheniumSelectivityCombinatorial chemistryMedicinal chemistryOrganic chemistrySalt (chemistry)Catalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCyclopropane Reaction Mechanisms