A Modular Approach to Dibenzo‐fused ϵ‐Lactams: Palladium‐Catalyzed Bridging‐C−H Activation. (18th August 2020)

• Record Type: Journal Article
• Authors: Yu, Yinghua; Ma, Liyao; Xia, Jiajin; Xin, Luoting; Zhu, Lei; Huang, Xueliang
• Is Part Of: Angewandte Chemie. Volume 132:Number 41(2020)
• Page Start: 18418
• Page End: 18423
• Publication Date: 2020-08-18
• Subjects: C−H activation -- collective synthesis -- homogeneous catalysis -- palladium -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202007799
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Tricyclic ring systems possessing a dibenzo structure joined to a seven‐membered heterocyclic ring frequently show important biological activities. However, a modular approach to these molecules based on efficient intermolecular reaction of readily available chemicals is lacking. Herein, an unprecedented palladium‐catalyzed formal [4+3] annulation for modular construction of these tricyclic systems is described. This reaction features easily accessible reactants ( o ‐haloarylaldehydes and N ‐tosylhydrazones), broad substrate scope, and excellent functional group compatibility. The synthetic potential is demonstrated by the easy scale‐up reactions, late‐stage modification of complex molecules, and collective synthesis of bioactive molecules and approved drugs. Abstract : A modular approach to access dibenzo‐fused ϵ‐lactams through palladium‐catalyzed bridging‐C−H activation is described. The reaction employs easily accessible chemicals as reactants and displays broad substrate scope with good functional‐group compatibility. The synthetic utility of this method is demonstrated by the collective synthesis of nine biologically active molecules.