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Selective Arene Cleavage by Direct Insertion of Iridium into the Aromatic Ring
Author(s) -
Jakoobi Martin,
Halcovitch Nathan,
Whitehead George F. S.,
Sergeev Alexey G.
Publication year - 2017
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.201611409
Subject(s) - iridium , ring (chemistry) , cleavage (geology) , chemistry , bond cleavage , ring strain , metal , inert , stereochemistry , insertion reaction , materials science , catalysis , organic chemistry , fracture (geology) , composite material
We report an unprecedented selective cleavage of aromatic C−C bonds through the insertion of well‐defined iridium complexes into the aromatic ring of simple alkylarenes. The insertion occurs at 50–100 °C without the activation of weaker C−H and C−C bonds and gives unique metallacycles in high yields. Key to the success of this approach is metal‐induced deformation of the arene ring, which creates temporary ring strain and promotes direct and selective insertion of the metal into the otherwise inert arene ring C−C bonds.