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2022 , Vol. 42 >Issue 11: 3766 - 3775

DOI: https://doi.org/10.6023/cjoc202205031

研究论文

环状三价碘试剂参与的β-二羰基化合物的α-苯甲酰氧基化反应

  • 高珠鹏 ,
  • 项锴 ,
  • 徐学涛 ,
  • 张雅婷 ,
  • 朱道勇
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  • a兰州大学药学院 兰州 730000
    b北京航天试验技术研究所 北京 100074
    c五邑大学生物科技与大健康学院 广东江门 529020

收稿日期: 2022-05-18

  修回日期: 2022-06-30

  网络出版日期: 2022-07-21

基金资助

广东省教育厅(2017KTSCX185); 广东省教育厅(2017KSYS010); 广东省教育厅(2019KZDXM035); 甘肃省科技计划(20JR10RA608)

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α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents

  • Zhupeng Gao ,
  • Kai Xiang ,
  • Xuetao Xu ,
  • Yating Zhang ,
  • Daoyong Zhu
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  • aSchool of Pharmacy, Lanzhou University, Lanzhou 730000
    bBeijing Institute of Aerospace Testing Technology, Beijing 100074
    cSchool of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020
*E-mail: ;

Received date: 2022-05-18

  Revised date: 2022-06-30

  Online published: 2022-07-21

Supported by

Department of Education of Guangdong Province(2017KTSCX185); Department of Education of Guangdong Province(2017KSYS010); Department of Education of Guangdong Province(2019KZDXM035); Science and Technology Program of Gansu Province(20JR10RA608)

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摘要

报道了利用环状三价碘试剂进行底物极性反转, 一锅法获得β-二羰基类底物α-苯甲酰氧基化产物的新方法. 反应成功的关键在于体系中原位生成了烯醇硅醚结构单元, 最终经过电性诱导极性反转中间体的氧化还原重排而完成转化. 该反应具有良好的原子经济性, 不仅适合克级规模制备和后续衍生化应用, 而且拓展了环状三价碘及其衍生物在极性反转领域的应用范围.

关键词： 三价碘试剂; β-二羰基化合物; α-苯甲酰氧基化; 极性反转

本文引用格式

高珠鹏 , 项锴 , 徐学涛 , 张雅婷 , 朱道勇 . 环状三价碘试剂参与的β-二羰基化合物的α-苯甲酰氧基化反应[J]. 有机化学, 2022 , 42(11) : 3766 -3775 . DOI: 10.6023/cjoc202205031

Abstract

A one-pot method for the α-benzoyloxylation of β-dicarbonyl compounds using trivalent iodine reagent was developed. The success of this protocol hinges on the the in situ generation of silylenol ether structure followed by electrical property-promoted reductive rearrangement of a umpolung intermediate. This reaction has good atomic economy, which is not only suitable for gram scale preparation and subsequent derivatization applications, but also expands the application range of cyclic trivalent iodine and its derivatives in the field of polarity reversal.

Key words： trivalent iodine reagent; β-dicarbonyl compound; α-benzoyloxylation; umpolung

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