Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N–S Bond Cleavage Strategy
Bo‐Sheng Zhang, Fan Wang, Xue‐Ya Gou, Ying-Hui Yang, Wan-Yuan Jia, Yong‐Min Liang, Xi‐Cun Wang, Yuke Li, Zheng‐Jun Quan
Abstract
In palladium/norbornene (Pd/NBE) chemistry, the “ortho effect” has been proven to be a key factor in the process of β-carbon elimination to extrude NBE. Herein, we found that the o-iodoaniline protected by a p-methoxybenzenesulfonyl group can recover the “ortho effect” and then undergo N–S bond cleavage with vinyl palladium, thus achieving a highly selective C–N coupling reaction in the Catallani–Lautens reaction system. On the basis of this discovery, a one-step synthesis of highly functionalized tricyclic indole derivatives was realized.
Topics & Concepts
ChemistryPalladiumCatalysisTricyclicNorborneneCleavage (geology)Indole testCombinatorial chemistryBond cleavageMedicinal chemistryStereochemistryOrganic chemistryFracture (geology)EngineeringGeotechnical engineeringMonomerPolymerCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques