Pd(II)-Catalyzed Annulation Reactions of Epoxides with Benzamides to Synthesize Isoquinolones
Huihong Wang, Fei Cao, Weiwei Gao, Xiaodong Wang, Yuhang Yang, Tao Shi, Zhen Wang
Abstract
Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C-H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.
Topics & Concepts
ChemistryAnnulationCatalysisAlkylationReagentCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques