有机化学 ›› 2021, Vol. 41 ›› Issue (9): 3511-3520.DOI: 10.6023/cjoc202106011 上一篇    下一篇

所属专题: 热点论文虚拟合集

研究论文

以芳基碘为碘化试剂的苯酚衍生物的位点选择性C—H键碘化反应

张涛a, 李尚达b,*(), 周春林b, 王新超b, 张孟b, 高泽众b, 李纲b,*()   

  1. a 中北大学理学院 山西太原 030051
    b 中国科学院福建物质结构研究所 煤制乙二醇及相关技术重点实验室 福州 350002
  • 收稿日期:2021-06-06 修回日期:2021-06-07 发布日期:2021-06-07
  • 通讯作者: 李尚达, 李纲
  • 基金资助:
    国家自然科学基金(22022111); 国家自然科学基金(22071248); 福建省自然科学基金(2020J02008); 福建省自然科学基金(2020J01108); 中国科学院青年创新促进会(2020306)

Site-Selective C—H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent

Tao Zhanga, Shangda Lib(), Chunlin Zhoub, Xinchao Wangb, Meng Zhangb, Zezhong Gaob, Gang Lib()   

  1. a School of Science, North University of China, Taiyuan, Shanxi 030051
    b Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002
  • Received:2021-06-06 Revised:2021-06-07 Published:2021-06-07
  • Contact: Shangda Li, Gang Li
  • Supported by:
    National Natural Science Foundation of China(22022111); National Natural Science Foundation of China(22071248); Natural Science Foundation of Fujian Province(2020J02008); Natural Science Foundation of Fujian Province(2020J01108); Youth Innovation Promotion Association of the Chinese Academy of Sciences(2020306)

富电子苯酚类化合物的位点选择性C—H键碘化是一个挑战性的反应. 报道了一类钯催化的、利用4-碘基-3-硝基苯甲醚为温和的碘化试剂, 实现无保护2-芳基苯酚和2-苯氧乙酸类化合物的C—H键碘化反应. 该反应适用于一系列富电子的苯酚类衍生物, 且能够获得优秀的位点选择性和良好的官能团耐受性. 结果表明, 对于具有挑战性底物的C—H键碘化, 经由形式复分解的C—H键碘化反应是一个潜在的有用方法.

关键词: C—H键碘化, 形式复分解, 位点选择性, 苯酚, 芳基碘化物, 钯催化

Site-selective C—H iodination of electron-rich phenols is a challenging reaction. A Pd(II)-catalyzed C—H iodination of free 2-aryl phenols and 2-phenoxyacetic acids using 4-iodo-3-nitroanisole as the mild iodinating reagent was reported. Excellent site-selectivity and good functional group tolerance were obtained with a range of electron rich phenol derivatives. These results suggest that C—H iodination via formal metathesis is a potentially useful method for C—H iodination of challenging substrates.

Key words: C—H iodination, formal metathesis, site-selectivity, phenol, aryl iodide, palladium catalysis