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
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  • 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
共同第一作者

收稿日期: 2022-07-05

  修回日期: 2022-07-29

  网络出版日期: 2022-09-15

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
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  • Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063
These authors contributed equally to this work.

Received date: 2022-07-05

  Revised date: 2022-07-29

  Online published: 2022-09-15

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)

摘要

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.

本文引用格式

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 . 氧杂蒽与亚磺酸钠的电化学氧化C(sp3)—H磺酰化反应[J]. 有机化学, 2023 , 43(1) : 186 -194 . DOI: 10.6023/cjoc202207012

Abstract

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.

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