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Palladium‐Catalyzed Bromoalkynylation of CC Double Bonds: Ring‐Structure‐Dependent Synthesis of 7‐Alkynyl Norbornanes and Cyclobutenyl Halides
Author(s) -
Li Yibiao,
Liu Xiaohang,
Jiang Huanfeng,
Liu Bifu,
Chen Zhengwang,
Zhou Peng
Publication year - 2011
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.201100002
Subject(s) - palladium , norbornene , chemistry , cycloaddition , catalysis , norbornane , ring (chemistry) , combinatorial chemistry , stereochemistry , polymer chemistry , medicinal chemistry , organic chemistry , polymerization , polymer
Strain versus flexibility : The palladium‐catalyzed reaction of haloalkynes with norbornene derivatives leads to 7‐alkynyl norbornane products (see scheme). Key to the success of this reaction is the formation of a “bridging” palladium species, which can rearrange to result in a C‐7 functionalization. The ring‐structure‐dependent [2+2] cycloaddition of haloalkynes with cyclooctene has been achieved in moderate to good yields under similar conditions.