Palladium‐Catalyzed Heck/Insertion/Decarboxylation Domino Sequence: Synthesis of Dihydrocyclohepta[<i>de</i>]naphthalenes
Cai He, Xiang‐Long Chen, Shi‐Yi Zhuang, Yan‐Dong Wu, Bo‐Cheng Tang, An‐Xin Wu
Abstract
Abstract A Pd‐catalyzed cascade cyclization for the construction of fused dihydrocyclohepta[ de ]naphthalene skeletons was developed. The skeleton was assembled from 3‐iodo‐4 H ‐chromen‐4‐one, norbornene and 8‐bromo‐1‐naphthoic acid. Unlike the classic Catellani reaction, which involves the removal of norbornene, in the present system, norbornene acts as a building block for the construction of rigid nonplanar molecular architectures rather than as an ortho ‐directing transient mediator. This synthesis involves the formation of three C−C bonds via a one‐pot process, and it is compatible of a series of substituents. magnified image
Topics & Concepts
ChemistryNorbornenePalladiumDecarboxylationDominoCatalysisStereochemistryCascadeSequence (biology)Combinatorial chemistryOrganic chemistryPolymerChromatographyMonomerBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAxial and Atropisomeric Chirality Synthesis