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

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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01395480
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Submitted on : Thursday, November 10, 2016 - 5:10:33 PM
Last modification on : Friday, July 10, 2020 - 4:26:37 PM

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Saravanakumar Elangovan, Jacob Neumann, Jean-Baptiste Sortais, Kathrin Junge, Christophe Darcel, et al.. Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes. Nature Communications, Nature Publishing Group, 2016, 7 (1), pp.12641. ⟨10.1038/ncomms12641⟩. ⟨hal-01395480⟩

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