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Azulenesulfonium Salts: Accessible, Stable, and Versatile Reagents for Cross‐Coupling
Author(s) -
Cowper Paul,
Jin Yu,
Turton Michael D.,
KociokKöhn Gabriele,
Lewis Simon E.
Publication year - 2016
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.201510666
Subject(s) - sulfonium , azulene , halide , reagent , chemistry , coupling reaction , coupling (piping) , combinatorial chemistry , organic chemistry , salt (chemistry) , materials science , catalysis , metallurgy
Azulenesulfonium salts may be readily prepared from the corresponding azulenes by an S E Ar reaction. These azulene sulfonium salts are bench‐stable species that may be employed as pseudohalides for cross‐coupling. Specifically, their application in Suzuki–Miyaura reactions has been demonstrated with a diverse selection of coupling partners. These azulenesulfonium salts possess significant advantages in comparison with the corresponding azulenyl halides, which are known to be unstable and difficult to prepare in pure form.