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Synthesis of Aromatic Compounds by Catalytic CC Bond Activation of Biphenylene or Angular [3]Phenylene
Author(s) -
Korotvička Aleš,
Císařová Ivana,
Roithová Jana,
Kotora Martin
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103888
Subject(s) - biphenylene , chemistry , alkyne , phenanthrenes , catalysis , moiety , ring (chemistry) , cyclobutane , medicinal chemistry , phenylene , ferrocene , stereochemistry , organic chemistry , phenanthrene , polymer , electrode , electrochemistry
Substituted phenanthrenes and picenes were easily prepared by reaction of biphenylene or angular [3]phenylene with various alkynes in the presence of a catalytic amount of [IrCl(cod)] 2 /dppe (cod=1,5‐cyclooctadiene, dppe=1,2‐bis(diphenylphosphino)ethane). The reaction is based on CC bond activation of the cyclobutane ring. The reaction tolerates the presence of bulky groups on the alkyne, such as the ferrocene moiety. In addition, a catalytic system based on [RhCl(cod)] 2 /dppe enabled the, hitherto unreported, reaction of biphenylene with nitriles to provide phenanthridines.