Wang Miao, Jiang Shan, Lu Xin-Xin, Zhang Kun, Yuan Zi-Yi, Xu Rui-Li, Zhao Bang-Tun, Wu An-Xin
College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471022, P. R. China.
National Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, Central China Normal University, Wuhan 430079, P.R. China.
Org Biomol Chem. 2023 Jul 26;21(29):5949-5952. doi: 10.1039/d3ob00902e.
Here, an efficient leaving group-activated methylene alcohol strategy for the preparation of primary propargyl alcohols from terminal alkynes by employing the bulk industrial product rongalite as the C1 unit has been described. The reaction avoids the low-temperature reaction conditions and inconvenient lithium reagents required for the classical method of preparing primary propargylic alcohols. Preliminary mechanistic studies showed that the reaction may not proceed formaldehyde intermediates, but through the direct nucleophilic attack of the terminal alkyne on the carbon atom of rongalite by activation through SO as a leaving group.
在此，已描述了一种高效的离去基团活化亚甲基醇策略，该策略通过使用大宗工业产品雕白粉作为C1单元，从末端炔烃制备伯炔丙醇。该反应避免了经典方法制备伯炔丙醇所需的低温反应条件和不便的锂试剂。初步机理研究表明，该反应可能不是通过甲醛中间体进行的，而是通过SO作为离去基团活化，使末端炔烃直接对雕白粉的碳原子进行亲核进攻。
