中国化学快报(英文版)2024，Vol.35Issue(1) ：227-232.DOI:10.1016/j.cclet.2023.108303

Iron/B2pin2 catalytic system enables the generation of alkyl radicals from inert alkyl C-O bonds for amine synthesis

Yanqing Zhu Shuai Chen Zhen Zhou Yun He Zhengli Liu Yang Liu Zhang Feng
中国化学快报(英文版)2024，Vol.35Issue(1) ：227-232.DOI:10.1016/j.cclet.2023.108303
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Iron/B2pin2 catalytic system enables the generation of alkyl radicals from inert alkyl C-O bonds for amine synthesis

Yanqing Zhu 1Shuai Chen 1Zhen Zhou 1Yun He 1Zhengli Liu 2Yang Liu 3Zhang Feng2
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作者信息

  • 1. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research,School of Pharmaceutical Sciences,Chongqing University,Chongqing 401331,China
  • 2. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research,School of Pharmaceutical Sciences,Chongqing University,Chongqing 401331,China;Affiliated Hospital of North Sichuan Medical College and Medical Imaging Key Laboratory of Sichuan Province,Nanchong 637503,China
  • 3. Department of Medicinal Chemistry,School of Pharmacy,Fujian Medical University(FMU),Fuzhou 350005,China
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Abstract

A method for the generation of alkyl radicals from inert alkyl C-O bonds has been developed via an iron/borane reagent/alkoxide catalytic system,which can be employed for the synthesis of amines from nitroarenes with excellent efficiency.This reductive amination features good functional group compatibil-ity and enables the late-stage amination of bio-relevant compounds,thus providing good opportunities for applications in medicinal chemistry.Preliminary mechanistic studies reveal that the amine synthesis may be involving a Fe/Li cation-assisted single electron transfer pathway to form alkyl radicals,and the low-valent iron species may be the active intermediates.

Key words

C-N bond formation/Reductive amination/Borane reagent/Iron catalysis/Green chemistry

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基金项目

国家自然科学基金(22271031)

国家自然科学基金(22201026)

重庆市自然科学基金(CSTB2022NSCQ-MSX1065)

Chongqing Postdoctoral Science Foundation(cstc2020jcyjbshX0052)

Medical Imaging Key Laboratory of Sichuan Province(MIKL202201)

Medical Imaging Key Laboratory of Sichuan Province(MIKL202202)

Affiliated Hospital of North Sichuan Medical College(2022JB001)

Youth Project of science and Technology Research Program of Chongqing Education Commission of China(KJQN201900112)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCDCSCD
影响因子：0.771
ISSN：1001-8417
参考文献量73
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