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Shaping Antiaromatic π‐Systems by Metalation: Synthesis of a Bowl‐Shaped Antiaromatic Palladium Norcorrole
Author(s) -
Yonezawa Tsubasa,
Shafie Siham A.,
Hiroto Satoru,
Shinokubo Hiroshi
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.201706134
Subject(s) - antiaromaticity , metalation , intramolecular force , palladium , chemistry , copper , metal , molecule , photochemistry , stereochemistry , organic chemistry , aromaticity , catalysis
The synthesis of a bowl‐shaped antiaromatic molecule was achieved through the deformation of a planar antiaromatic porphyrinic π‐conjugation system by insertion of palladium into the small cavity of a metal‐free norcorrole. The bowl‐to‐bowl inversion dynamics of the antiaromatic Pd‐coordinated norcorrole was determined by variable‐temperature 1 H NMR spectroscopy. The metal‐free norcorrole was prepared from acid‐induced demetalation of a copper norcorrole, which was obtained from the intramolecular coupling of a bis(diiododipyrrin) copper complex with copper thiophenecarboxylate.