Chemoselective RuO4 oxidation of phenyl or p-methoxyphenyl groups to carboxylic acid functions in the presence of a tetrahydropyran ring

被引：28

作者：

Miranda, LSM ^{[1
]}

Vasconcellos, MLAA ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, LAb H0 27, Nucl Pesquisas Prod Nat, BR-21941590 Rio De Janeiro, RJ, Brazil

来源：

SYNTHESIS-STUTTGART | 2004年 / 11期

关键词：

oxidation; catalysis; aromatic; ruthenium tetroxide; tetrahydropyran; Prins reaction; Barbier reaction;

D O I：

10.1055/s-2004-829119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the first example of a chemoselective oxidation of phenyl and p-methoxyphenyl groups to carboxylic acid functions in the presence of a tetrahydropyran ring, using 0.02 mol% of RuCl3 and a co-oxidant. The use of NaIO4 as co-oxidant in H2O-CH3CN-CCl4 as the solvent system led to diketone 7. The change of the co-oxidant from sodium periodate to periodic acid and removal of water from the solvent system led to carboxylic acid 2 in good yield as the sole product.

引用

页码：1767 / 1770

页数：4

共 25 条

[1] Metal-mediated reductive hydrodehalogenation of organic halides [J].