Palladium‐Catalyzed Heck/Insertion/Decarboxylation Domino Sequence: Synthesis of Dihydrocyclohepta[de]naphthalenes. Issue 14 (24th May 2021)

• Record Type: Journal Article
• Authors: He, Cai; Chen, Xiang‐Long; Zhuang, Shi‐Yi; Wu, Yan‐Dong; Tang, Bo‐Cheng; Wu, An‐Xin
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 14(2021)
• Page Start: 3476
• Page End: 3480
• Publication Date: 2021-05-24
• Subjects: Pd-catalyzed -- cascade; norbornene -- dihydrocyclohepta[de]naphthalene; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100401
• Languages: English
• ISSNs: 1615-4150

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. Abstract :