Alkane oxygenation catalysed by gold complexes
Author(s)
Date issued
2001
In
Tetrahedron Letters
Vol
41
No
42
From page
7253
To page
7256
Subjects
alkanes alkyl hydroperoxides biomimetics gold complexes homogeneous catalysis hydrogen peroxide hydroperoxidation molecular oxygen oxidation oxygenation GIF-TYPE CONDITIONS II-FE-IV SATURATED-HYDROCARBONS METAL-COMPLEXES MICROCOCCUS-LUTEUS ATMOSPHERIC OXYGEN CENTERED RADICALS AEROBIC OXIDATION AU-PROTEIN IRON
Abstract
Gold(III) and gold(I) complexes, NaAuCl4 and ClAuPPh3, efficiently catalyse the oxidation of alkanes by H2O2 in acetonitrile solution at 75 degreesC. Turnover numbers (TONs) attain 520 after 144 h. Alkyl hydroperoxides are the main products, whereas ketones (aldehydes) and alcohols are formed in smaller concentrations. It is suggested on the basis of the bond selectivity study that at least one of the pathways in Au-catalysed alkane hydroperoxidation does not involve the participation of free hydroxyl radicals. Possibly, the oxidation begins from the alkane hydrogen atom abstraction by a gold oxo species. The oxidation of cyclooctane by air at room temperature catalysed by NaAuCl4 in the presence of Zn/CH3COOH as a reducing agent and methylviologen as an electron-transfer agent gave cyclooctanol (TON = 10). (C) 2001 Published by Elsevier Science Ltd.
Publication type
journal article