Room-Temperature Copper Cross-Coupling Reactions of Anilines with Aryl Bromides

Dueker, Jonas and Petersen, Nele and Richter, Noah and Feuerer, Paul and Faber, Teresa and Hoelter, Niklas and Kehl, Niklas and Oboril, Jan and Strippel, Julian and Groeer, Alexander and Guimond, Nicolas and Kaldas, Sherif J. and Luebbesmeyer, Maximilian and Volpin, Giulio and Koenig, Burkhard and Hillenbrand, Julius (2025) Room-Temperature Copper Cross-Coupling Reactions of Anilines with Aryl Bromides. ORGANIC LETTERS, 27 (22). pp. 5566-5571. ISSN 1523-7060, 1523-7052

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Abstract

We present a novel copper-catalyzed method for aniline cross-couplings promoted by a 6-hydroxy picolinhydrazide ligand. The method achieves room-temperature reactivity with aryl bromides, enabled by a methanol/ethanol solvent mixture and a mild, functional group-compatible base, with catalyst loadings as low as 0.5 mol %. The use of industrially preferred solvents and base, as well as the high catalytic activity, offers a significant advancement in the practicality and scalability of industrial processes. Furthermore, the approach extends to the cross-coupling of aryl chlorides under elevated temperatures and demonstrates compatibility with additional nucleophile classes.

Item Type: Article
Uncontrolled Keywords: (HETERO)ARYL CHLORIDES; CATALYZED AMINATION; DIMETHYL-SULFOXIDE; N-ARYLATION; PALLADIUM; HALIDES; LIGAND; EFFICIENT; SOLVENT
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Jul 2026 09:04
Last Modified: 14 Jul 2026 09:04
URI: https://pred.uni-regensburg.de/id/eprint/66492

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