Shaping Antiaromatic π‐Systems by Metalation: Synthesis of a Bowl‐Shaped Antiaromatic Palladium Norcorrole | Zendy

Yonezawa Tsubasa | Zendy; Shafie Siham A. | Zendy; Hiroto Satoru | Zendy; Shinokubo Hiroshi | Zendy

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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.

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