4.8 Article

Coupled Flavin-Iodine Redox Organocatalysts: Aerobic Oxidative Transformation from N-Tosylhydrazones to 1,2,3-Thiadiazoles

Journal

ACS CATALYSIS
Volume 7, Issue 8, Pages 4986-4989

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b01535

Keywords

redox organocatalyst; flavin; iodine; aerobic oxidation; thiadiazole

Funding

  1. JSPS/MEXT KAKENHI [16K05797, 26105724]
  2. Sumitomo Foundation
  3. Cooperative Research Program of the Institute for Protein Research, Osaka University [CR-16-05]
  4. Grants-in-Aid for Scientific Research [26105724, 16K05797] Funding Source: KAKEN

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A bioinspired two-component redox organocatalyst system using 1,10-bridged flavinium and NH4I was developed to perform environmentally friendly aerobic oxidative ring formation of 1,2,3-thiadiazoles from N-tosylhydrazones and sulfur. The redox organocatalysis of the flavinium promoted the iodine-catalyzed system without the use of any sacrificial reagents, except for environmentally benign molecular oxygen.

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