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Ruthenium‐Catalyzed Monoalkenylation of Aromatic Ketones by Cleavage of Carbon–Heteroatom Bonds with Unconventional Chemoselectivity
Author(s) -
Kondo Hikaru,
Akiba Nana,
Kochi Takuya,
Kakiuchi Fumitoshi
Publication year - 2015
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.201503641
Subject(s) - chemoselectivity , ruthenium , heteroatom , chemistry , cleavage (geology) , catalysis , bond cleavage , aromaticity , photochemistry , medicinal chemistry , organic chemistry , molecule , ring (chemistry) , materials science , fracture (geology) , composite material
Ruthenium‐catalyzed selective monoalkenylation of ortho CO or CN bonds of aromatic ketones was achieved. The reaction allowed the direct comparison of the relative reactivities of the cleavage of different carbon‐heteroatom bonds, thus suggesting an unconventional chemoselectivity, where smaller, more‐electron‐donating groups are more easily cleaved. Selective monofunctionalization of CO bonds in the presence of ortho CH bonds was also achieved.