Iron-Catalyzed Cyclotrimerization of Terminal Alkynes by Dual Catalyst Activation in the Absence of Reductants

Brenna, Davide and Villa, Matteo and Gieshoff, Tim N. and Fischer, Fabian and Hapke, Marko and Jacobi von Wangelin, Axel (2017) Iron-Catalyzed Cyclotrimerization of Terminal Alkynes by Dual Catalyst Activation in the Absence of Reductants. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56 (29). pp. 8451-8454. ISSN 1433-7851, 1521-3773

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Abstract

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 degrees 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.

Item Type: Article
Uncontrolled Keywords: 2+2+2 CYCLOADDITION; INTRAMOLECULAR CYCLOTRIMERIZATION; HETEROGENEOUS CATALYSIS; ORGANIC-SYNTHESIS; COMPLEXES; DIYNES; METAL; HYDROGENATIONS; TRIYNES; alkynes; arene synthesis; cyclotrimerization; iron; nanoparticles
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Axel Jacobi von Wangelin
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Dec 2018 13:16
Last Modified: 11 Feb 2019 14:39
URI: https://pred.uni-regensburg.de/id/eprint/1548

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