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2023 , Vol. 43 >Issue 4: 1483 - 1491

DOI: https://doi.org/10.6023/cjoc202208031

研究论文

环丁酮类腙参与的偕二氟环丙烷开环胺化反应

  • 梁志鹏 ,
  • 叶浩 ,
  • 张海滨 ,
  • 姜国民 ,
  • 吴新星
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  • a 南通大学化学化工学院 江苏南通 226019
    b 南通职业大学药品与环境工程学院 江苏南通 226019
    c 江苏浩丰生物科技有限公司 江苏南通 226019

收稿日期: 2022-08-24

  修回日期: 2022-11-02

  网络出版日期: 2022-12-12

基金资助

国家自然科学基金(22201145); 南通大学高层次人才科研基金(03083031); 江苏省高校自然科学研究(21KJB150015); 南通大学大型仪器开放基金(KFJN2215)

收起

Ring Opening Amination of gem-Difluorocyclopropanes with Cyclobutanone Hydrazones

  • Zhipeng Liang ,
  • Hao Ye ,
  • Haibin Zhang ,
  • Guomin Jiang ,
  • Xinxing Wu
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
    b College of Pharmaceutical and Environmental Engineering, Nantong Vocational University, Nantong, Jiangsu 226019
    c Jiangsu Haofeng Bio-technology Co., Ltd., Nantong, Jiangsu 226019
* Corresponding author. ;

Received date: 2022-08-24

  Revised date: 2022-11-02

  Online published: 2022-12-12

Supported by

National Natural Science Foundation of China(22201145); Scientific Research Foundation of High-level Talents of Nantong University(03083031); Universities Natural Science Research Project of Jiangsu Province(21KJB150015); Large Instruments Open Foundation of Nantong University(KFJN2215)

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摘要

以环丁酮类腙和偕二氟环丙烷为原料, 通过钯催化的偕二氟环丙烷开环和氮中心的亲核捕获过程, 以中等至优秀的收率合成了一系列N-氟代烯丙基腙四元环化合物. 该方法具有较强的官能团兼容性和良好的底物普适性, 同时适用于克级规模反应制备.

关键词： 环丁酮类腙; 偕二氟环丙烷; 开环反应; 单氟烯烃

本文引用格式

梁志鹏 , 叶浩 , 张海滨 , 姜国民 , 吴新星 . 环丁酮类腙参与的偕二氟环丙烷开环胺化反应[J]. 有机化学, 2023 , 43(4) : 1483 -1491 . DOI: 10.6023/cjoc202208031

Abstract

N-Fluoroallyl hydrazones with four-ring structure were effectively synthesized using cyclobutanone hydrazones and gem-difluorocyclopropanes as raw materials through palladium catalyzed ring opening of difluorocyclopropanes and nucleophilic capture process of nitrogen nucleophile. This protocol shows broad substrate scope and good functional group tolerance, which can be applied for gram-scale preparation.

Key words： cyclobutanone hydrazone; gem-difluorocyclopropane; ring opening reaction; monofluoroalkene

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