Reduction of Nitroarenes with Hydrogen Transfer Catalysis

Authors:
  • JQJ. F. Quinn
    J. F. Quinn
  • CBC. E. Bryant
    C. E. Bryant
  • KGK. C. Golden
    K. C. Golden
  • BGB. T. Gregg
    B. T. Gregg
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Abstract
The reduction of nitroarenes to the corresponding anilines via hydrogen transfer catalysis was described. Thus, the catalytic reduction of nitroarenes 1a-f was carried out with 1,4-cyclohexadiene (2) as a hydrogen transfer source to give the corresponding anilines 3a-f in 70-99% yield. The Pd/C-catalyzed hydrogenation of the chloro-substituted nitroarenes 1g,h gave aniline (4) and 3-aminopyridine (5) in 99% yield, while the Pt/C-mediated reduction gave 4-chloroaniline (3g) and 3-amino-2-chloropyridine (3h) with good selectivity (3g/4 = 75:25, 3h/5 = 79:19).