Development of environmentally benign substitution reaction system

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Homogeneous gold-catalyzed nucleophilic substitution reaction was developed by use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents. The reactions with alkanethiols proceeded smoothly to give alkyl sulfides in high yields. The reactions with silyl enol ethers produced alpha-alkylated silyl enol ethers. Treatment of the eliminated isochoumarin with base followed by DMC gave the starting materials in high yields. To conduct this reaction system with heterogeneous catalysts, catalytic properties of nanoporous gold have been investigated. This material exhibited remarkable catalytic activities in benzannulation and oxidation of organic silanes.