4.6 Article

Red light-induced conjugation of amines through amide bond formation triggered via photooxidation of 3-acylindolizines

Journal

COMMUNICATIONS CHEMISTRY
Volume 5, Issue 1, Pages -

Publisher

NATURE PORTFOLIO
DOI: 10.1038/s42004-022-00712-5

Keywords

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Funding

  1. JSPS KAKENHI [JP22K05325]
  2. Japan Agency for Medical Research and Development (AMED) [JP21am0401021, JP21am0101098]
  3. Cooperative Research Project of Research Center for Biomedical Engineering
  4. Pioneering Project Chemical Probe
  5. RIKEN

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We introduce a new method for amide bond formation based on the photoreaction of 3-acylindolizines with amines triggered by red-light irradiation. This method allows for the synthesis of conjugated amides in a short time with high yields. It is applicable to various aliphatic amines with different functional groups and can be conducted in aqueous organic solvents.
The development of a conjugation method initiated by irradiation of long-wavelength light (>500 nm) to prepare densely functionalized molecules while avoiding undesired photodegradation has attracted considerable attention. Here we show an amide bond formation method based on the photoreaction of 3-acylindolizines in the presence of amines triggered via red-light irradiation. Photooxidation of 3-acylindolizines using a catalytic amount of a photosensitizer and red light-emitting diodes (660 nm) affords the corresponding conjugated amides in nearly quantitative yields within <5 min. This transformation can be performed in aqueous organic solvents and is applicable to diverse aliphatic amines with various functional groups, including the moieties responsive to short-wavelength light. Photoinduced conjugation has been broadly used for functionalization of molecules but is limited by possible photodegradation. Here, the authors report a robust amide bond formation method based on the photoreaction of 3-acylindolizines with amines triggered via red-light irradiation in nearly quantitative yields within less than 5 min.

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