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

Saravanakumar Elangovan, Jacob Neumann, Jean-Baptiste Sortais, Kathrin Junge, Christophe Darcel and Matthias Beller ()
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Saravanakumar Elangovan: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
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

Nature Communications, 2016, vol. 7, issue 1, 1-8

Abstract: 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.

Date: 2016
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DOI: 10.1038/ncomms12641

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