Cross‐Coupling Reaction of a Highly Strained Molecule: Synthesis of σ–π Conjugated Tetrahedranes | Zendy

Kobayashi Yuzuru | Zendy; Nakamoto Masaaki | Zendy; Inagaki Yusuke | Zendy; Sekiguchi Akira | Zendy

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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.

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