Gold-Catalyzed Dimerization of Diarylalkynes: Direct Access to Azulenes
M. Sc. Vanessa Claus
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorMichael Schukin
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorSiegfried Harrer
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorDr. Matthias Rudolph
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorDr. Frank Rominger
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Crystallographic analysis.
Search for more papers by this authorProf. Dr. Abdullah M. Asiri
Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589 Saudi Arabia
Search for more papers by this authorDr. Jin Xie
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. A. Stephen K. Hashmi
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589 Saudi Arabia
Search for more papers by this authorM. Sc. Vanessa Claus
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorMichael Schukin
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorSiegfried Harrer
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorDr. Matthias Rudolph
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorDr. Frank Rominger
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Crystallographic analysis.
Search for more papers by this authorProf. Dr. Abdullah M. Asiri
Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589 Saudi Arabia
Search for more papers by this authorDr. Jin Xie
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. A. Stephen K. Hashmi
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589 Saudi Arabia
Search for more papers by this authorGraphical Abstract
A fully atom-economic gold-catalyzed reaction enables the direct synthesis of substituted azulenes from easily accessible starting materials. A fluorine substituent as a strong +M donor initiates this reaction. The obtained scaffolds can be easily functionalized at the seven-membered ring in a selective manner.
Abstract
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.
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