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A Modular Approach to Dibenzo‐fused ϵ‐Lactams: Palladium‐Catalyzed Bridging‐C−H Activation
Author(s) -
Yu Yinghua,
Ma Liyao,
Xia Jiajin,
Xin Luoting,
Zhu Lei,
Huang Xueliang
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202007799
Subject(s) - annulation , combinatorial chemistry , chemistry , palladium , molecule , tricyclic , intermolecular force , functional group , modular design , catalysis , ring (chemistry) , stereochemistry , organic chemistry , computer science , polymer , operating system
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.