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Stereocontrolled Synthesis of Benzo[ k ]fluoranthenes—An Unexpected Isomerization Mediated by Rhodacyclopentadiene
Author(s) -
Xu Shengjie,
Chen Kejuan,
Chen Hui,
Yao Jiannian,
Zhu Xiaozhang
Publication year - 2014
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.201405145
Subject(s) - isomerization , chemistry , aryl , stereochemistry , catalysis , medicinal chemistry , organic chemistry , alkyl
Herein, a Rh III ‐catalyzed stereocontrolled synthesis of benzo[ k ]fluoranthenes is reported. It was found that the unexpected E / Z isomerization was highly sensitive to the electronic effects of the substituents on the aryl groups. Theoretical calculations revealed that this controllable stereochemistry originates from the mediation of rhodacyclopentadiene intermediates during the isomerization. The fact that similar stereochemistry was observed when using an Ir III catalyst further suggests a certain generality of this discovery toward some other transition metals.