CAJ | 학술논문

发展了一种简单、高效、温和的卤代炔烃水合反应体系。在阳离子金催化剂的催化作用下，以二氯乙烷为溶剂，室温下卤代炔烃发生水合反应，高收率、高区域选择性地得到单一的α-卤代甲基酮化合物(收率≥91%)。该方法具有底物适用范围广、反应条件温和和环境友好等优点，为含α-卤代甲基酮结构单元的天然产物及复杂药物分子的合成提供了新方法。
발전료일충간단、고효、온화적서대결경수합반응체계。재양리자금최화제적최화작용하，이이록을완위용제，실온하서대결경발생수합반응，고수솔、고구역선택성지득도단일적α-서대갑기동화합물(수솔≥91%)。해방법구유저물괄용범위엄、반응조건온화화배경우호등우점，위함α-서대갑기동결구단원적천연산물급복잡약물분자적합성제공료신방법。
α-Halomethylketones are building blocks for the synthesis of various compounds due to their selective transformations with different reagents. Moreover, a wide range of α-halomethylketone derivatives at-tract increasing interests in pharmaceutical chemistry. α-Halomethylketones are also widespread used as inter-mediates in organic synthesis, such as in Favorskii rearrangement and Reformatsky reaction. However, their direct synthesis from the corresponding methylktones by N-halosuccinimides, molecular halogen and metal halides has been plagued by poor regioselectivity and over-halogenation. For the above reasons, a simple, convenient and environmentally benign protocol to synthesize the α-halomethylketones was developed by cata-lytic hydration of haloalkynes, which can be easily prepared in one step from commercial terminal alkynes. In the presence of 3% (molar fraction) BrettPhosAuNTf2 and 3 mmol H2 O in dichloroethane at room temperature, a broad range of haloalkynes were converted into α-halomethylketones in excellent yield through gold-catalyzed hydration reaction. The presented methodology will provide new strategies for α-halomethylketones-type drug design and synthesis, which has important academic significance and application value.