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Cubane Cross‐Coupling and Cubane–Porphyrin Arrays
Author(s) -
Bernhard Stefan S. R.,
Locke Gemma M.,
Plunkett Shane,
Meindl Alina,
Flanagan Keith J.,
Senge Mathias O.
Publication year - 2018
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.201704344
Subject(s) - cubane , porphyrin , sonogashira coupling , coupling (piping) , aryl , chemistry , core (optical fiber) , palladium , combinatorial chemistry , stereochemistry , catalysis , molecule , photochemistry , materials science , organic chemistry , alkyl , metallurgy , composite material
Herein, an improved methodology for aryl‐cubane cross‐coupling is reported. The peculiarities of the cubane core and its behavior during cross‐coupling conditions were analyzed, while the versatility of this adapted Baran cross‐coupling methodology was demonstrated by the synthesis of various aryl‐cubane systems, including coupling products of cubanes and porphyrins. Furthermore, arm extension of alkynyl‐cubanes by Sonogashira reactions is demonstrated, showcasing the first proof of the stability of the cubane core in the presence of palladium catalysts.