Premium
Iron‐Catalyzed Cyclotrimerization of Terminal Alkynes by Dual Catalyst Activation in the Absence of Reductants
Author(s) -
Brenna Davide,
Villa Matteo,
Gieshoff Tim N.,
Fischer Fabian,
Hapke Marko,
Jacobi von Wangelin Axel
Publication year - 2017
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.201705087
Subject(s) - catalysis , regioselectivity , chemistry , deprotonation , substrate (aquarium) , toluene , dual role , combinatorial chemistry , metal , medicinal chemistry , organic chemistry , ion , oceanography , geology
Catalyzing C−C bond‐forming reactions with earth‐abundant metals under mild conditions is at the heart of sustainable synthesis. The cyclotrimerization of alkynes is a valuable atom‐efficient reaction in organic synthesis that is enabled by several metal catalysts, including iron. This study reports an effective iron‐catalyzed cyclotrimerization for the regioselective synthesis of 1,2,4‐substituted arenes (1 mol % catalyst, toluene, 20 °C, 5 min). A dual activation mechanism (substrate deprotonation, reductive elimination) renders the simple Fe II precatalyst highly active in the absence of any reductant.