有机化学 ›› 2023, Vol. 43 ›› Issue (12): 4251-4260.DOI: 10.6023/cjoc202303011 上一篇    下一篇

研究论文

无过渡金属条件下二芳基硒化合物的合成

孙婧, 张萌萌, 锅小龙, 王琪, 王陆瑶*()   

  1. 首都师范大学化学系 北京 100048
  • 收稿日期:2023-03-06 修回日期:2023-05-29 发布日期:2023-07-27
  • 基金资助:
    国家自然科学基金(22074095); “十三五”期间北京市属高校高水平教师(CIT&TCD20190330)

Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst

Jing Sun, Mengmeng Zhang, Xiaolong Guo, Qi Wang, Luyao Wang*()   

  1. Department of Chemistry, Capital Normal University, Beijing 100048
  • Received:2023-03-06 Revised:2023-05-29 Published:2023-07-27
  • Contact: *E-mail: xdwly@163.com
  • Supported by:
    National Natural Science Foundation of China(22074095); High-Level Teachers in Beijing Municipal Universities in the Period of 13th Five Year Plan(CIT&TCD20190330)

报道了一种以二芳基硒醚为硒基来源, K2S2O8为氧化剂, 在无过渡金属条件下对N-芳基酰胺化合物的C(sp2)—H键直接官能化, 合成了系列二芳基硒化合物的方法. 机理研究表明, 该反应经过单电子转移的自由基历程, 中间体的稳定性决定了反应的选择性. 该反应官能团兼容性好, 位点选择性强, 操作简便, 成本低廉, 是一种实用的二芳基硒化合物的合成方法.

关键词: 无过渡金属催化, C—Se键构建, 区域选择性

A series of diaryl selenium compounds were synthetized from N-arylamide compounds and diphenyl diselenide, using K2S2O8 as oxidant without any transition metal catalyst. Mechanistic studies reveal that the reaction proceeds a single-electron transfer radical process. The dominant products are o-substituted and p-substituted product, depending on the stability of intermediates. The synthetic reaction exhibits some outstanding advantages, such as substrate tolerance, high regioselectivity, convenience and low-price.

Key words: transition metal-free, construction of C—Se bond, regional selectivity