4.7 Article

Photoinduced Kochi Decarboxylative Elimination for the Synthesis of Enamides and Enecarbamates from N-Acyl Amino Acids

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 5, Pages 2933-2940

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00167

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Funding

  1. National Science Foundation [CHE-1800147]
  2. Kansas Bioscience Authority Rising Star program
  3. NSF Academic Research Infrastructure [9512331]
  4. NIH Shared Instrumentation Grant [S10RR024664]
  5. NSF Major Research Instrumentation Grant [0320648]

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Decarboxylative elimination of easily accessible N-acyl amino acids to provide enamide and enecarbamate building blocks has been realized through the combination of an organophotoredox catalyst and copper acetate as the terminal oxidant. This operationally simple process utilizes inexpensive and readily available reagents without preactivation of the carboxylic acid. Enamides and enecarbamates are now accessible directly from N-acyl amino acids consequently improving upon the utility of Kochi's oxidative decarboxylation of carboxylic acids.

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