Selective N-monoalkylation of aromatic amines with benzylic alcohols by a hydrogen autotransfer process catalyzed by unmodified magnetite

Ricardo Martínez; Diego J. Ramón; Miguel Yus

doi:10.1039/B901929D

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Organic & Biomolecular Chemistry

Issue 10, 2009

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Selective N-monoalkylation of aromatic amines with benzylic alcohols by a hydrogen autotransfer process catalyzed by unmodified magnetite

Ricardo Martínez , Diego J. Ramón and Miguel Yus

Org. Biomol. Chem., 2009, 7, 2176-2181

DOI: 10.1039/B901929D
Received 29 Jan 2009, Accepted 05 Mar 2009
First published on the web 02 Apr 2009

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Abstract
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A new catalyst for an old material: magnetite is a good catalyst for the selective N-alkylation of aromatic amines using benzylic alcohols as electrophiles. The process could be repeated up to eight times without losing effectiveness. The catalyst recycling is very easy, using a simple magnet. The catalyst is selective and could discriminate between aromatic and aliphatic amines, as well as between benzylic and aliphatic alcohols, as the reactions only take place with aromatic amines and benzylic alcohols.

Abstract from Methods in Organic Synthesis 2009

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Supplementary Info

TEM images of magnetite after and before being used, as wellas ¹H and ¹³C NMR for compounds 3a–n
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Organic & Biomolecular Chemistry

Selective N-monoalkylation of aromatic amines with benzylic alcohols by a hydrogen autotransfer process catalyzed by unmodified magnetite

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