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Metal‐Mediated Synthesis of Antiaromatic Porphyrinoids from a BODIPY Precursor
Author(s) -
Sakida Takafumi,
Yamaguchi Shigeru,
Shinokubo Hiroshi
Publication year - 2011
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.201006314
Subject(s) - antiaromaticity , trimer , stille reaction , chemistry , dimer , metal , photochemistry , stereochemistry , aromaticity , molecule , organic chemistry , catalysis
Metallic route to antiaromaticity : The synthesis of a butadiyne‐bridged cyclic BODIPY dimer (see structure; C white, B orange, N blue, F green) and trimer was achieved through Pd‐catalyzed Stille coupling and Cu‐mediated Glaser‐type coupling. These cyclic BODIPYs were found to be stable 24π‐ and 36π‐antiaromatic porphyrinoids with planar conformations, and their structures, electronic states, and reactivity were explored.