Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (12): 4275-4281.DOI: 10.6023/cjoc202209041 Previous Articles     Next Articles

Special Issue: 自由基化学专辑



郑煜a, 钱沈城a, 徐鹏程a, 郑斌南c, 黄申林a,b,*()   

  1. a 南京林业大学化学工程学院 江苏省林业资源高效加工利用协同创新中心 南京 210037
    b 林产化学与材料国际创新高地 南京 210037
    c 宁夏佰斯特医药化工有限公司 银川 750411
  • 收稿日期:2022-09-30 修回日期:2022-11-24 发布日期:2022-12-07
  • 通讯作者: 黄申林
  • 基金资助:
    国家自然科学基金(32171724); 江苏省自然科学基金(BK20210607)

Electrochemical Oxidative Thiocyanosulfonylation of Aryl Acetylenes

Yu Zhenga, Shencheng Qiana, Pengcheng Xua, Binnan Zhengc, Shenlin Huanga,b()   

  1. a Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037
    b International Innovation Center for Forest Chemicals and Materials, Nanjing 210037
    c Ningxia Best Pharmaceutical Chemical Co. Ltd., Yinchuan 750411
  • Received:2022-09-30 Revised:2022-11-24 Published:2022-12-07
  • Contact: Shenlin Huang
  • Supported by:
    National Natural Science Foundation of China(32171724); Natural Science Foundation of Jiangsu Province(BK20210607)

Thiocyano and sulfonyl groups as important functional groups are widely existing in natural products, agrochemicals and medicines. They are also versatile synthetic intermediates that could be converted into various functionalities. There are limited reports on the synthesis of compounds that contain these two functional groups. A simple three-component thiocyanatosulfonylation of aryl acetylenes with sodium sulfinates and NH4SCN through electrochemical oxidation to construct thiocyanated vinylsulfones has been established. The reaction employs easily accessible starting materials and features the characterization of external oxidant-free, mild reaction conditions, and high stereoselectivity. Moreover, this method enables two C—S bonds to be simultaneously formed in a one-step reaction.

Key words: alkyne, difunctionalization, electrochemistry, radical, thiocyanation, sulfonylation, green chemistry