Intermolecular C–H Aminocyanation of Indoles via Copper–iodine Cocatalyzed Tandem C–N/C–C Bond Formation
Wenhua Yu, Xiaoxiang Zhang, Chenrui Liu, Yingying Zhang, Xiaoting Gu, Jiahao Liao, Zhuan Zhang, Wanxing Wei, Guanghua Li, Taoyuan Liang
Abstract
An efficient copper-iodine cocatalyzed intermolecular C-H aminocyanation of indoles with a broad substrate scope has been developed for the first time. This method enables highly step-economic access to 2-amino-3-cyanoindoles in moderate to good yields and provides a complementary strategy for the regioselective difunctionalization of carbon═carbon double bonds of interest in organic synthesis and related areas. Mechanistic studies suggest that these transformations are initiated by iodine-mediated C2-H amination with azoles, followed by copper-catalyzed C3-H cyanation with ethyl cyanoformate.
Topics & Concepts
ChemistryAminationCyanationIntermolecular forceIodineRegioselectivityCopperTandemCatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryMoleculeMaterials scienceComposite materialCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques