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2023 , Vol. 43 >Issue 11: 3966 - 3976

DOI: https://doi.org/10.6023/cjoc202305021

研究论文

碘介导下通过氧化性C—C键形成合成β-硝基胺与α-胺基腈类化合物

  • 李倩敏 ,
  • 王漫漫 ,
  • 于文全 ,
  • 常俊标
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  • a 郑州大学化学学院 绿色催化中心 郑州 450001
    b 郑州大学化工学院 绿色催化中心 郑州 450001
†共同第一作者

收稿日期: 2023-05-15

  修回日期: 2023-06-23

  网络出版日期: 2023-07-06

基金资助

河南省疫情防控应急科研攻关(221111311400); 河南省高等学校青年骨干教师培养计划(2021GGJS012); 国家自然科学基金(82130103)

收起

Synthesis of β-Nitroamines and α-Aminonitriles by I2-Mediated Oxidative C—C Bond Formation

  • Qianmin Li ,
  • Manman Wang ,
  • Wenquan Yu ,
  • Junbiao Chang
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  • a Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001
    b School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001
†These authors contributed equally to this work.
* E-mail: ;

Received date: 2023-05-15

  Revised date: 2023-06-23

  Online published: 2023-07-06

Supported by

Henan Province Epidemic Prevention and Control Emergency Research Project(221111311400); Young Backbone Teachers Fund of Henan Province(2021GGJS012); National Natural Science Foundation of China(82130103)

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摘要

以分子碘为单一氧化剂, 开发了一种无过渡金属催化的C—C键形成反应. 该反应可通过易得的叔胺分别与硝基烷、三甲基氰硅烷和亚磷酸酯合成β-硝基胺、α-胺基腈和α-胺基膦酸酯类化合物. 该合成方法具有操作简单, 底物适用范围广, 而且可以成功实现克级规模的合成.

关键词： 碘; C—C键形成; 叔胺; β-硝基胺; α-胺基腈

本文引用格式

李倩敏 , 王漫漫 , 于文全 , 常俊标 . 碘介导下通过氧化性C—C键形成合成β-硝基胺与α-胺基腈类化合物[J]. 有机化学, 2023 , 43(11) : 3966 -3976 . DOI: 10.6023/cjoc202305021

Abstract

A transition-metal-free C—C bond formation reaction is developed employing molecular iodine as the sole oxidant to access β-nitroamines, α-aminonitriles and α-aminophosphonates from readily accessible tertiary amines with nitroalkanes, trimethylsilyl cyanide and phosphite, respectively. The present synthetic approach is operationally simple, has a broad substrate scope, and can be successfully conducted on a gram scale.

Key words： iodine; C—C bond formation; tertiary amine; β-nitroamine; α-aminonitrile

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