4.7 Article

Visible-light promoted sulfonamidation of enol acetates to α-amino ketones based on redox-neutral photocatalysis

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 22, Pages 3771-3775

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9qo01119f

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Funding

  1. Scientific Research Fund of Hunan Provincial Education Department [18B106]
  2. Science and Technology Planning Project of Hunan Province [2018TP1017]
  3. DFG (Graduiertenkolleg Photocatalysis) [1626]

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A visible-light mediated photoredox-catalyzed sulfonamidation of enol acetates to alpha -amino ketones has been developed. Upon irradiation with a blue LED (lambda 425 +/- 15 nm) in the presence of catalytic amounts of Ir(ppy)(3) (2 mol%), N-arylsulfonyl-1-aminopyridine salts were transformed into N-centered radical intermediates, which then underwent coupling with enol acetates to give alpha -sulfonylamino ketones in up to 83% yield. The process features mild and operationally simple reaction conditions and does not require an external oxidant.

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