Qi Zhenjie, Wen Si-Miaomiao, Wu Quansen, Jiang Dong-Fang, Hao Wen-Juan, Jiang Bo
Department of Engineering, Jining University, Qufu 273155, Shandong, China.
Hunan Provincial Key Laboratory of the Research and Development of Novel Pharmaceutical Preparations, Provincial First-Class Applied Discipline (Pharmacy), Changsha Medical University, Changsha 410000, China.
J Org Chem. 2023 Aug 18;88(16):11874-11884. doi: 10.1021/acs.joc.3c01163. Epub 2023 Aug 3.
A direct arylsulfonylation of β,γ-unsaturated hydrazones method, in which sulfonated pyrazolines are accessed by a three-component reaction of β,γ-unsaturated hydrazones, DABSO, and aryldiazonium tetrafluoroborates, has been developed without external oxidants or catalysts. This transformation is triggered by the formation of arylsulfonyl radicals in situ from the reaction of aryldiazonium tetrafluoroborates and DABSO, and is enabled by controllable generation of C center radical, in which DABSO was utilized as the sulfone source and an oxidant in this radical-mediated cascaded reaction. A wide range of substrates can be applied in this process to afford pyrazolines in good yield, and it is amenable for gram-scale synthesis.
一种β，γ-不饱和腙的直接芳基磺酰化方法已被开发出来，该方法通过β，γ-不饱和腙、DABSO和芳基四氟硼酸重氮盐的三组分反应得到磺化吡唑啉，无需外部氧化剂或催化剂。这种转化是由芳基四氟硼酸重氮盐与DABSO反应原位生成芳基磺酰基自由基引发的，并通过可控生成C中心自由基实现，其中DABSO在这种自由基介导的级联反应中用作砜源和氧化剂。该方法可应用于多种底物，以良好的产率得到吡唑啉，并且适用于克级规模的合成。
