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Iron catalysed direct alkylation of amines with alcohols

Tao Yan, Ben L Feringa () and Katalin Barta ()
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Tao Yan: Stratingh Institute for Chemistry, University of Groningen
Ben L Feringa: Stratingh Institute for Chemistry, University of Groningen
Katalin Barta: Stratingh Institute for Chemistry, University of Groningen

Nature Communications, 2014, vol. 5, issue 1, 1-7

Abstract: Abstract The selective conversion of carbon–oxygen bonds into carbon–nitrogen bonds to form amines is one of the most important chemical transformations for the production of bulk and fine chemicals and pharma intermediates. An attractive atom-economic way of carrying out such C–N bond formations is the direct N-alkylation of simple amines with alcohols by the borrowing hydrogen strategy. Recently, transition metal complexes based on precious metals have emerged as suitable catalysts for this transformation; however, the crucial change towards the use of abundant, inexpensive and environmentally friendly metals, in particular iron, has not yet been accomplished. Here we describe the homogeneous, iron-catalysed, direct alkylation of amines with alcohols. The scope of this new methodology includes the monoalkylation of anilines and benzyl amines with a wide range of alcohols, and the use of diols in the formation of five, six- and seven- membered nitrogen heterocycles, which are privileged structures in numerous pharmaceuticals.

Date: 2014
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms6602

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DOI: 10.1038/ncomms6602

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