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Palladium‐Catalyzed Heck/Insertion/Decarboxylation Domino Sequence: Synthesis of Dihydrocyclohepta[ de ]naphthalenes
Author(s) -
He Cai,
Chen XiangLong,
Zhuang ShiYi,
Wu YanDong,
Tang BoCheng,
Wu AnXin
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100401
Subject(s) - chemistry , norbornene , palladium , decarboxylation , domino , catalysis , stereochemistry , cascade , sequence (biology) , combinatorial chemistry , organic chemistry , polymer , monomer , chromatography , biochemistry
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.