Unified Oxidation Protocol for the Synthesis of Carbonyl Compounds Using a Manganese Catalyst

作者：Kamijo Shin; Amaoka Yuuki; Inoue Masayuki^*

来源：Synthesis (Germany), 2010, 2010(14): 2475-2489.

DOI：10.1055/s-0029-1218809

• catalysis
• oxidation
• ethers
• alcohols
• ketones
• carboxylic acids

We have developed a unified protocol for the oxidation of ethers, benzylic compounds, and alcohols to carbonyl compounds. The protocol uses catalytic amounts of manganese(II) chloride tetrahydrate and 4,4',4 ''-tri(t-butyl)-2,2':6',2 ''-terpyridine in combination with a stoichiometric amount of either m-chloroperbenzoic acid (MCPBA) or potassium hydrogen peroxysulfate (KHSO(5)). A reagent system consisting of the Mn catalyst and MCPBA permitted the chemoselective sp(3) C-H oxidation of alkyl ethers and benzylic compounds to generate the corresponding ketones. Alternatively, the water-soluble inorganic salt KHSO(5) in combination with the Mn catalyst was used to oxidize alcohols to ketones or carboxylic acids. Importantly, the Mn catalyst/KHSO(5) system eliminates technical difficulties associated with the isolation of carboxylic acid products. All the oxidations presented in this feature article proceed at sub-ambient temperature in an aerobic atmosphere, and can therefore be used in practical syntheses of complex organic molecules.

• 出版日期2010-7