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Gold‐Catalyzed Dimerization of Diarylalkynes: Direct Access to Azulenes
Author(s) -
Claus Vanessa,
Schukin Michael,
Harrer Siegfried,
Rudolph Matthias,
Rominger Frank,
Asiri Abdullah M.,
Xie Jin,
Hashmi A. Stephen K.
Publication year - 2018
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.201805918
Subject(s) - catalysis , cationic polymerization , chemistry , aryl , atom (system on chip) , combinatorial chemistry , trapping , photochemistry , medicinal chemistry , polymer chemistry , organic chemistry , computer science , alkyl , embedded system , ecology , biology
We have developed a simple gold‐catalyzed procedure for the synthesis of substituted and modifiable azulenes. The azulenes are formed either by the dimerization of push–pull diarylalkynes bearing a fluorine atom in ortho or para position or by the dimerization of a symmetric electron‐rich diarylalkyne. In the presence of a cationic gold catalyst, the two alkynes can form a highly reactive vinyl cation. Trapping of this high‐energy intermediate by an appropriate aryl unit then delivers substituted azulenes in a single step and in a perfect atom economy.