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2023 , Vol. 43 >Issue 12: 4251 - 4260

DOI: https://doi.org/10.6023/cjoc202303011

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
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  • 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

  网络出版日期: 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)

收起

Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst

  • Jing Sun ,
  • Mengmeng Zhang ,
  • Xiaolong Guo ,
  • Qi Wang ,
  • Luyao Wang
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  • Department of Chemistry, Capital Normal University, Beijing 100048
*

Received date: 2023-03-06

  Revised date: 2023-05-29

  Online published: 2023-07-27

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)

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摘要

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

本文引用格式

孙婧 , 张萌萌 , 锅小龙 , 王琪 , 王陆瑶 . 无过渡金属条件下二芳基硒化合物的合成[J]. 有机化学, 2023 , 43(12) : 4251 -4260 . DOI: 10.6023/cjoc202303011

Abstract

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

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