Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3144-3156.DOI: 10.6023/cjoc202102025 Previous Articles     Next Articles


t-BuOK促进的还原脱砜/脱氢反应: 选择性合成2-取代的1,3-共轭二烯及其应用

孙佳兵a, 苗涛a,*(), 李品华a, 王磊a,b,c,*()   

  1. a 淮北师范大学化学与材料科学学院 绿色和精准合成化学及应用教育部重点实验室 安徽淮北 235000
    b 台州学院医药化工与材料工程学院 浙江台州 318000
    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:2021-02-09 修回日期:2021-05-07 发布日期:2021-05-25
  • 通讯作者: 苗涛, 王磊
  • 基金资助:
    国家自然科学基金(21772062); 国家自然科学基金(22071171); 国家自然科学基金(21602072); 安徽省高校自然科学基金(KJ2019ZD66)

t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions

Jiabing Suna, Tao Miaoa(), Pinhua Lia, Lei Wanga,b,c()   

  1. a Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huabei, Anhui 235000
    b Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang 318000
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2021-02-09 Revised:2021-05-07 Published:2021-05-25
  • Contact: Tao Miao, Lei Wang
  • Supported by:
    National Natural Science Foundation of China(21772062); National Natural Science Foundation of China(22071171); National Natural Science Foundation of China(21602072); Anhui University Natural Science Research Project(KJ2019ZD66)

A t-BuOK-mediated desulfonylation/dehydrogenation cascade reaction of (Z)-C6-(vinyl sulfone)phenanthridines is described. This process provides a novel and efficient strategy for the synthesis of 1,3-dienes with phenanthridinyl units in good yields under transition-metal-free conditions. Furthermore, the application of the generated 1,3-dienes in the [4+2] cycloaddition has been demonstrated by reacting with dienophiles such as fumaronitrile in a two-step procedure.

Key words: t-BuOK, desulfonylation, 1,3-conjugated dienes, cycloaddition reactions