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

被引：68

作者：

Ahlsten, Nanna ^{[1
]}

Lundberg, Helena ^{[1
]}

Martin-Matute, Belen ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

来源：

GREEN CHEMISTRY | 2010年 / 12卷 / 09期

基金：

瑞典研究理事会;

关键词：

TRANSITION-METAL-COMPLEXES; HIGHLY EFFICIENT CATALYSTS; CARBONYL-COMPOUNDS; REDOX ISOMERIZATION; AQUEOUS-MEDIA; CARBENE COMPLEXES; ORGANIC-REACTIONS; GREEN CHEMISTRY; MECHANISM; KETONES;

D O I：

10.1039/c004964f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An environmentally benign method for the transformation of allylic alcohols into carbonyl compounds is described. Using [Rh(COD(CH(3)CN)(2)]BF(4) (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.

引用

页码：1628 / 1633

页数：6

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