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Open AccessOpen Access JUSTC Chemistry 18 January 2023

Nickel-catalyzed alkene ipso-selective reductive hydroamination with nitroarenes

  • Department of Applied Chemistry, University of Science and Technology of China, Hefei 230026, China

Cite this:
https://doi.org/10.52396/JUSTC-2022-0119
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  • Author Bio:

    Zhen Li is a master’s student under the supervision of Prof. Yao Fu at the University of Science and Technology of China. His research mainly focuses on nickel-catalyzed alkene hydroalkylation

    Xi Lu received his Ph.D. degree from the University of Science and Technology of China in 2016. He is currently an Associate Researcher at the University of Science and Technology of China. His research mainly focuses on base-metal-catalyzed alkyl-alkyl bond formation

    Yao Fu received his Ph.D. degree from the University of Science and Technology of China in 2005. He is currently a Professor at the University of Science and Technology of China. His research focuses on physical organic chemistry, green organic synthesis, and the biomass chemical industry

  • Corresponding author: E-mail: luxi@mail.ustc.edu.cn; E-mail: fuyao@ustc.edu.cn
  • Received Date: 29 August 2022
  • Accepted Date: 20 October 2022
    • Available Online: 18 January 2023
    Abstract

  • Abstract

    Aromatic amine synthesis via reductive coupling between alkenes and nitroarenes is attractive; however, it remains underdeveloped. Herein, we report a nickel-catalyzed alkene hydroamination with nitroarenes under mild reductive conditions. This reaction exhibited an ipso-selectivity and enabled repaid preparation of aromatic amines with primary and secondary alkyl groups. Many functional groups were well tolerated, providing an efficient approach for drug-like arylamine synthesis.

    Graphical abstract

    Aromatic amines with primary and secondary alkyl groups could be accessed through nickel-catalyzed ipso-selective alkene hydroamination with nitroarenes.

    Abstract

    Aromatic amine synthesis via reductive coupling between alkenes and nitroarenes is attractive; however, it remains underdeveloped. Herein, we report a nickel-catalyzed alkene hydroamination with nitroarenes under mild reductive conditions. This reaction exhibited an ipso-selectivity and enabled repaid preparation of aromatic amines with primary and secondary alkyl groups. Many functional groups were well tolerated, providing an efficient approach for drug-like arylamine synthesis.

    • Public Summary

    • A nickel-catalyzed ipso-selective alkene hydroamination with nitroarenes under mild reductive conditions was developed.
    • Repaid preparation of aromatic amines with primary and secondary alkyl groups and compatibility with many functional groups were demonstrated.
    • Based on the literature and mechanistic investigation, a plausible reaction mechanism involving in situ generation of alkylnickel intermediates and reaction with in situ generated nitrosoarenes was proposed.

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    • References(54)
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    Figure  1.  State-of-the-art aromatic amine synthesis and our strategy. DG = directing group; FG = functional group; DEMS = diethoxymethylsilane; diglyme = 2-methoxyethyl ether; TBAI = tetrabutylammonium iodide.

    Figure  2.  Scope of substrates. Standard conditions: nitroarene (0.20 mmol, 1.0 equiv.), alkene (0.40 mmol, 2.0 equiv.), NiBr2(diglyme) (0.02 mmol, 10 mol%), L8 (0.03 mmol, 15 mol%), DEMS (2.0 mmol, 10.0 equiv.), Na2CO3 (0.60 mmol, 3.0 equiv.), TBAI (0.10 mmol, 0.5 equiv.), Mg powder (0.10 mmol, 0.5 equiv.), solvent (1,4-dioxane∶MeOH = 5∶1, 1.20 mL, 0.167 mol/L), 50 °C, 12 h. The yield represents the isolated yield of the major product. The reaction regioselectivity was determined by GC analysis of the reaction mixture. aFor these cases, the reaction regioselectivity could not be determined by GC analysis, 1H NMR determined regioisomeric ratios shown in the table after chromatography purification. bL1 instead of L8 as ligand. DEMS = Diethoxymethylsilane; TBAI = Tetrabutylammonium iodide.

    Figure  3.  Synthetic applications. Standard conditions are shown in Fig. 2. aThe yield represents the total GC yield. The reaction regioselectivity was determined by GC analysis of the reaction mixture. bThe yield represents the isolated yield of the major product. The reaction regioselectivity was determined by GC analysis of the reaction mixture. cYields reported in reference. dThe yield represents the isolated yield of the major product. Regioselectivity could not be determined by GC analysis. The regioisomeric ratio was determined to be >20∶1.0 l∶b by 1H NMR after chromatography purification. DCMI-PHOS = dicyclohexyl(2-mesityl-1H-inden-1-yl)phosphine; DME = 1,2-dimethoxyethane; dba = dibenzylideneacetone.

    Figure  4.  Mechanistic investigation. Standard conditions: nitroarene or potential intermediate (0.20 mmol, 1.0 equiv. or 0.10 mmol, 0.5 equiv.), alkene (0.40 mmol, 2.0 equiv.), NiBr2(diglyme) (0.02 mmol, 10 mol%), L8 (0.03 mmol, 15 mol%), DEMS (2.0 mmol, 10.0 equiv.), Na2CO3 (0.60 mmol, 3.0 equiv.), TBAI (0.10 mmol, 0.5 equiv.), Mg powder (0.10 mmol, 0.5 equiv.), solvent (1,4-dioxane∶ MeOH = 5∶1, 1.20 mL, 0.167 mol/L), 50 °C, 12 h. Yields and regioisomeric ratios were determined by GC analysis with triphenylmethane as an internal standard. Total yield for the mixture of the linear product and branched product.

    Figure  5.  Plausible reaction mechanism.

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    Zhang Z, Bera S, Fan C, et al. Streamlined alkylation via nickel-hydride-catalyzed hydrocarbonation of alkenes. J. Am. Chem. Soc., 2022, 144 (16): 7015–7029. doi: 10.1021/jacs.1c13482
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    Pirnot M T, Wang Y M, Buchwald S L. Copper hydride catalyzed hydroamination of alkenes and alkynes. Angew. Chem. Int. Ed., 2016, 55 (1): 48–57. doi: 10.1002/anie.201507594
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    Waser J, Gaspar B, Nambu H, et al. Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins. J. Am. Chem. Soc., 2006, 128 (35): 11693–11712. doi: 10.1021/ja062355+
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