有机化学 ›› 2023, Vol. 43 ›› Issue (1): 186-194.DOI: 10.6023/cjoc202207012 上一篇    下一篇

研究论文

氧杂蒽与亚磺酸钠的电化学氧化C(sp3)—H磺酰化反应

危斌, 周子龙, 秦景灏*(), 严泽宇, 郭嘉程, 雷澍, 谢叶香, 欧阳旋慧*(), 宋仁杰*()   

  1. 南昌航空大学 江西省持久性污染物控制与资源回收重点实验室 南昌 330063
  • 收稿日期:2022-07-05 修回日期:2022-07-29 发布日期:2022-09-15
  • 通讯作者: 秦景灏, 欧阳旋慧, 宋仁杰
  • 作者简介:
    共同第一作者
  • 基金资助:
    国家自然科学基金(51878326); 国家自然科学基金(21861027); 国家自然科学基金(22161030); 国家自然科学基金(21901100); 江西省自然科学基金(20212ACB203007); 江西省自然科学基金(20204BCJ23010); 江西省自然科学基金(20202ACBL216017); 江西省自然科学基金(20212AEI91002); 江西省自然科学基金(20202ACB203002); 江西省教育厅自然科学基金(GJJ210906); 江西省教育厅自然科学基金(GJJ210909)

Electrochemical Oxidative C(sp3)—H Sulfonylation of Xanthenes with Sodium Sulfinates

Bin Wei, Zilong Zhou, Jinghao Qin(), Zeyu Yan, Jiacheng Guo, Shu Lei, Yexiang Xie, Xuanhui Ouyang(), Renjie Song()   

  1. Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063
  • Received:2022-07-05 Revised:2022-07-29 Published:2022-09-15
  • Contact: Jinghao Qin, Xuanhui Ouyang, Renjie Song
  • About author:
    These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(51878326); National Natural Science Foundation of China(21861027); National Natural Science Foundation of China(22161030); National Natural Science Foundation of China(21901100); Natural Science Foundation of Jiangxi Province(20212ACB203007); Natural Science Foundation of Jiangxi Province(20204BCJ23010); Natural Science Foundation of Jiangxi Province(20202ACBL216017); Natural Science Foundation of Jiangxi Province(20212AEI91002); Natural Science Foundation of Jiangxi Province(20202ACB203002); Natural Science Foundation of Jiangxi Provincial Education Department(GJJ210906); Natural Science Foundation of Jiangxi Provincial Education Department(GJJ210909)

研究了氧杂蒽与亚硫酸钠的C(sp3)—H键的直接电化学磺酰化反应. 在室温下一步合成了多种9-(芳基磺酰基)-9H氧杂蒽和9-(烷基磺酰基)-9H氧杂蒽. 该反应通过自由基途径进行, 并在该电化学磺酰化转化下形成新的C—S键. 这种策略的显著优点包括无需过渡金属和额外的氧化剂、反应条件温和、操作简单、底物范围广以及优异的官能团耐受性.

关键词: 电化学氧化, 磺酰化, 氧杂蒽, 亚磺酸钠

A direct electrochemical sulfonylation of C(sp3)—H bonds of xanthenes with sodium sulfinates was studied. A wide variety of 9-(arylsulfonyl)-9H-xanthenes and 9-(alkylsulfonyl)-9H-xanthenes were constructed in a single step at room temperature. This reaction proceeded through a radical pathway and a new C—S bond was formed under this electrochemical sulfonylation transformation. The significant advantages of this strategy include transition metal- and additional oxidant-free, mild reaction conditions, operational simplicity, broad substrate scope and excellent functional group tolerance.

Key words: electrooxidation, sulfonylation, xanthene, sodium sulfinate