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Catalysts 2017, 7(1), 27; doi:10.3390/catal7010027

Aziridine- and Azetidine-Pd Catalytic Combinations. Synthesis and Evaluation of the Ligand Ring Size Impact on Suzuki-Miyaura Reaction Issues

Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin-en-Yvelines, 45 Avenue des Etats-Unis, 78035 Versailles CEDEX, France
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Academic Editor: Ioannis D. Kostas
Received: 29 November 2016 / Revised: 4 January 2017 / Accepted: 10 January 2017 / Published: 13 January 2017
(This article belongs to the Special Issue Suzuki–Miyaura Cross-Coupling Reaction and Potential Applications)
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Abstract

The synthesis of new vicinal diamines based on aziridine and azetidine cores as well as the comparison of their catalytic activities as ligand in the Suzuki-Miyaura coupling reaction are described in this communication. The synthesis of three- and four-membered ring heterocycles substituted by a methylamine pendant arm is detailed from the parent nitrile derivatives. Complexation to palladium under various conditions has been examined affording vicinal diamines or amine-imidate complexes. The efficiency of four new catalytic systems is compared in the preparation of variously substituted biaryls. Aziridine- and azetidine-based catalytic systems allowed Suzuki-Miyaura reactions from aryl halides including chlorides with catalytic loadings until 0.001% at temperatures ranging from 100 °C to r.t. The evolution of the Pd-metallacycle ring strain moving from azetidine to aziridine in combination with a methylamine or an imidate pendant arm impacted the Suzuki-Miyaura reaction issue. View Full-Text
Keywords: aziridine; azetidine; vicinal diamine; imidate; ligand; Suzuki-Miyaura coupling aziridine; azetidine; vicinal diamine; imidate; ligand; Suzuki-Miyaura coupling
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MDPI and ACS Style

Boufroura, H.; Large, B.; Bsaibess, T.; Perato, S.; Terrasson, V.; Gaucher, A.; Prim, D. Aziridine- and Azetidine-Pd Catalytic Combinations. Synthesis and Evaluation of the Ligand Ring Size Impact on Suzuki-Miyaura Reaction Issues. Catalysts 2017, 7, 27.

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