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Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes

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  • Saravanakumar Elangovan

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock
    UMR 6226 CNRS—Université de Rennes 1 Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis—Centre for Catalysis and Green Chemistry)

  • Jacob Neumann

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

  • Jean-Baptiste Sortais

    (UMR 6226 CNRS—Université de Rennes 1 Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis—Centre for Catalysis and Green Chemistry)

  • Kathrin Junge

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

  • Christophe Darcel

    (UMR 6226 CNRS—Université de Rennes 1 Institut des Sciences Chimiques de Rennes, Team Organometallics: Materials and Catalysis—Centre for Catalysis and Green Chemistry)

  • Matthias Beller

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

Abstract

Borrowing hydrogen (or hydrogen autotransfer) reactions represent straightforward and sustainable C–N bond-forming processes. In general, precious metal-based catalysts are employed for this effective transformation. In recent years, the use of earth abundant and cheap non-noble metal catalysts for this process attracted considerable attention in the scientific community. Here we show that the selective N-alkylation of amines with alcohols can be catalysed by defined PNP manganese pincer complexes. A variety of substituted anilines are monoalkylated with different (hetero)aromatic and aliphatic alcohols even in the presence of other sensitive reducible functional groups. As a special highlight, we report the chemoselective monomethylation of primary amines using methanol under mild conditions.

Suggested Citation

  • Saravanakumar Elangovan & Jacob Neumann & Jean-Baptiste Sortais & Kathrin Junge & Christophe Darcel & Matthias Beller, 2016. "Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes," Nature Communications, Nature, vol. 7(1), pages 1-8, November.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms12641
    DOI: 10.1038/ncomms12641
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    Cited by:

    1. Robin Fertig & Felix Leowsky-Künstler & Torsten Irrgang & Rhett Kempe, 2023. "Rational design of N-heterocyclic compound classes via regenerative cyclization of diamines," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Duo Wei & Rui Sang & Peter Sponholz & Henrik Junge & Matthias Beller, 2022. "Reversible hydrogenation of carbon dioxide to formic acid using a Mn-pincer complex in the presence of lysine," Nature Energy, Nature, vol. 7(5), pages 438-447, May.
    3. He Zhao & Yang Wu & Chenggang Ci & Zhenda Tan & Jian Yang & Huanfeng Jiang & Pierre H. Dixneuf & Min Zhang, 2022. "Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis," Nature Communications, Nature, vol. 13(1), pages 1-11, December.

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