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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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Supplementary files

Article information


Submitted
08 Apr 2010
Accepted
07 Jul 2010
First published
16 Aug 2010

Green Chem., 2010,12, 1628-1633
Article type
Paper

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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