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Issue 9, 2010
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Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature

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Abstract

An environmentally benign method for the transformation of allylic alcohols into carbonyl compounds is described. Using [Rh(COD(CH3CN)2]BF4 (2) in combination with 1,3,5-triaza-7-phosphaadamantane (PTA, 1) as the catalytic system in water results in a very fast redox isomerisation of a variety of secondary allylic alcohols at ambient temperature. Also, some primary allylic alcohols can be isomerised into the corresponding aldehydes. The active complex, which in some cases can be used in catalyst loadings as low as 0.5 mol%, is formed in situ from commercially available reagents. Based on deuterium labelling studies, a tentative mechanism involving metal-enone intermediates is presented.

Graphical abstract: Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature

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Publication details

The article was received on 08 Apr 2010, accepted on 07 Jul 2010 and first published on 16 Aug 2010


Article type: Paper
DOI: 10.1039/C004964F
Citation: Green Chem., 2010,12, 1628-1633
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    Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature

    N. Ahlsten, H. Lundberg and B. Martín-Matute, Green Chem., 2010, 12, 1628
    DOI: 10.1039/C004964F

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