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Cross‐Coupling Reaction of a Highly Strained Molecule: Synthesis of σ–π Conjugated Tetrahedranes
Author(s) -
Kobayashi Yuzuru,
Nakamoto Masaaki,
Inagaki Yusuke,
Sekiguchi Akira
Publication year - 2013
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.201304770
Subject(s) - aryl , halide , conjugated system , palladium , coupling reaction , molecule , chemistry , catalysis , coupling (piping) , photochemistry , polymer chemistry , computational chemistry , combinatorial chemistry , materials science , organic chemistry , polymer , alkyl , metallurgy
Strain for an effect : The cross‐coupling reaction of highly strained tetrahedranes with aryl halides has been investigated. In the presence of a palladium catalyst, tetrahedryllithium rapidly reacted with various aryl halides to form aryl‐substituted tetrahedranes (see picture) in good to excellent yields. The UV/Vis absorption spectra suggest an extended σ–π conjugation between the σ orbital of the tetrahedrane core and the aryl π system.