金催化氧化末端炔烃合成α-乙酰氧基甲基酮方法研究

Gold(I)-Catalyzed Intermolecular Oxidation of Terminal Alkynes:Synthesis of α-Acetoxy Ketones

采用Ph3PAuNTf2作为催化剂,8-甲基喹啉氮氧化物为氧化剂,甲基磺酸为添加酸,金催化氧化末端炔烃与乙酸分子反应,室温下高效合成了一系列α-乙酰氧基甲基酮化合物.考察了氧化剂、催化剂结构、催化剂用量等因素对反应的影响,确定了最优反应条件,最高收率为90%.提出了α-羰基金卡宾对乙酸分子O—H键的卡宾反应机理.该方法具有操作简单、条件温和、产率高等特点,为含有α-乙酰氧基甲基酮结构的化合物合成提供了一条新的途径.

In the presence of Ph3PAuNTf2, 8-methylquinoline-N-oxide and MsOH, various of terminal alkynes were effi- ciently converted into the corresponding α-acetoxy ketones. The influences of oxidant, catalyst structure, catalyst loading and reaction media on the reaction were investigated, and the optimal reaction conditions were also obtained. The reaction is pro- posed to proceed via α-oxo gold carbene intermolecular reaction with acetic acids. The reaction method with its advantages of simple procedure, mild reaction conditions and high yield provides a novel valuable approach to α-acetoxy ketones from ter- minal alkynes.