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

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

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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.

C-N bond formationReductive aminationBorane reagentIron catalysisGreen chemistry

Yanqing Zhu、Shuai Chen、Zhen Zhou、Yun He、Zhengli Liu、Yang Liu、Zhang Feng

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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

Department of Medicinal Chemistry,School of Pharmacy,Fujian Medical University(FMU),Fuzhou 350005,China

国家自然科学基金国家自然科学基金重庆市自然科学基金Chongqing Postdoctoral Science FoundationMedical Imaging Key Laboratory of Sichuan ProvinceMedical Imaging Key Laboratory of Sichuan ProvinceAffiliated Hospital of North Sichuan Medical CollegeYouth Project of science and Technology Research Program of Chongqing Education Commission of China

2227103122201026CSTB2022NSCQ-MSX1065cstc2020jcyjbshX0052MIKL202201MIKL2022022022JB001KJQN201900112

2024

10.1016/j.cclet.2023.108303

中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子：0.771
ISSN：1001-8417
年,卷(期)：2024.35(1)
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