Mono-N-methylation of anilines with methanol catalyzed by a manganese pincer-complex
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Bruneau-Voisine, Antoine
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Wang, Ding
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Univ Rennes 1, Inst Sci Chim Rennes, UMR CNRS 6226, Team Organometall Mat & Catalysis, 263 Ave Gen Leclerc, F-35046 Rennes, FranceUniv Rennes 1, Inst Sci Chim Rennes, UMR CNRS 6226, Team Organometall Mat & Catalysis, 263 Ave Gen Leclerc, F-35046 Rennes, France
Wang, Ding
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Dorcet, Vincent
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Roisnel, Thierry
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Univ Rennes 1, Inst Sci Chim Rennes, UMR CNRS 6226, Ctr Diffractometrie X, 263 Ave Gen Leclerc, F-35046 Rennes, FranceUniv Rennes 1, Inst Sci Chim Rennes, UMR CNRS 6226, Team Organometall Mat & Catalysis, 263 Ave Gen Leclerc, F-35046 Rennes, France
Roisnel, Thierry
[2
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Darcel, Christophe
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Univ Rennes 1, Inst Sci Chim Rennes, UMR CNRS 6226, Team Organometall Mat & Catalysis, 263 Ave Gen Leclerc, F-35046 Rennes, FranceUniv Rennes 1, Inst Sci Chim Rennes, UMR CNRS 6226, Team Organometall Mat & Catalysis, 263 Ave Gen Leclerc, F-35046 Rennes, France
Darcel, Christophe
[1
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Sortais, Jean-Baptiste
[1
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[1] Univ Rennes 1, Inst Sci Chim Rennes, UMR CNRS 6226, Team Organometall Mat & Catalysis, 263 Ave Gen Leclerc, F-35046 Rennes, France
[2] Univ Rennes 1, Inst Sci Chim Rennes, UMR CNRS 6226, Ctr Diffractometrie X, 263 Ave Gen Leclerc, F-35046 Rennes, France
[3] Inst Univ France, 1 Rue Descartes, F-75231 Paris 05, France
The selective mono-N-methylation of anilines derivatives was achieved under mild conditions using inexpensive methanol as Cl source. Under hydrogen borrowing conditions, using a tridentate (PNP)-P-3 manganese pre-catalyst (5 mol%), a catalytic amount of base (20 mol%), for 24 h at 120 degrees C, a large variety of anilines derivatives was methylated in good to excellent yield. Mechanistic investigations allowed us to isolate and characterize by X-ray diffraction studies a de-aromatized manganese intermediate. (C) 2017 Elsevier Inc. All rights reserved.
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Technion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, IsraelTechnion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, Israel
Thenarukandiyil, Ranjeesh
Kamte, Rohit
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Technion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, IsraelTechnion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, Israel
Kamte, Rohit
Garhwal, Subhash
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Technion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, IsraelTechnion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, Israel
Garhwal, Subhash
Effnert, Philipp
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Westfalische Wilhelms Univ Munster, Dept Organ Chem, D-48149 Munster, GermanyTechnion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, Israel
Effnert, Philipp
Fridman, Natalia
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Technion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, IsraelTechnion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, Israel
Fridman, Natalia
de Ruiter, Graham
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Technion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, IsraelTechnion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, Israel
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Univ Stockholm, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenUniv Stockholm, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Wallner, OA
Szabó, KJ
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Univ Stockholm, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenUniv Stockholm, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden