有机化学 ›› 2024, Vol. 44 ›› Issue (3): 981-988.DOI: 10.6023/cjoc202310032 上一篇    下一篇

所属专题: 有机氟化学合辑

研究论文

N-苄基丙烯酰胺的电化学三氟甲基化/螺环化合成三氟甲基取代2-氮杂螺[4.5]癸烷

周兰a, 何红a, 杨德巧a, 侯中伟a,*(), 王磊a,b,c,*()   

  1. a 台州学院高等研究院药学院 浙江台州 318000
    b 杭州师范大学材料与化学化工学院 有机硅化学及材料技术教育部重点实验室 杭州 311121
    c 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032
  • 收稿日期:2023-10-31 修回日期:2023-12-16 发布日期:2024-04-02
  • 基金资助:
    国家自然科学基金(22071171); 国家自然科学基金(22101201); 浙江省自然科学基金(LZ22B020003); 浙江省自然科学基金(LQ22B020005)

Electrochemical Trifluoromethylation/Spirocyclization of N-Benzylacrylamides to Construct Trifluoromethylated 2-Azaspiro[4.5]decanes

Lan Zhoua, Hong Hea, De-Qiao Yanga, Zhong-Wei Houa(), Lei Wanga,b,c()   

  1. a Advanced Research Institute, School of Pharmaceutical Sciences, Taizhou University, Taizhou, Zhejiang 318000
    b College of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2023-10-31 Revised:2023-12-16 Published:2024-04-02
  • Contact: *E-mail: zhongwei.hou@tzc.edu.cn; leiwang88@hotmail.com
  • Supported by:
    National Natural Science Foundation of China(22071171); National Natural Science Foundation of China(22101201); Natural Science Foundation of Zhejiang Province(LZ22B020003); Natural Science Foundation of Zhejiang Province(LQ22B020005)

利用CF3SO2Na作为三氟甲基来源, 开发了N-苄基丙烯酰胺的电化学三氟甲基化/螺环化反应. 该方法在室温下于一个简单未分室电解池中进行, 无需依赖金属试剂和氧化剂, 为构建系列三氟甲基取代2-氮杂螺[4.5]癸烷提供了绿色和高效的路径. 此外, 反应易进行克级合成和转化.

关键词: 有机电化学, 三氟甲基化, 螺环化, 螺环产物

An electrochemical trifluoromethylation/spirocyclization of N-benzylacrylamides with CF3SO2Na as the source of trifluoromethyl group has been developed. This approach is carried out in a simple undivided cell at room temperature without relying on metal-reagents and oxidants, which provides a green and efficient route to construct a series of CF3-containing 2-azaspiro[4.5]decanes. Furthermore, the gram-scale synthesis and transformation can be easily performed.

Key words: organic electrochemistry, trifluoromethylation, spirocyclization, spiroproduct