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Green Aerobic Oxidation of Thiols to Disulfides by Flavin-Iodine Coupled Organocatalysis

Marina Oka, Ryo Kozako, Hiroki Iida*

*Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan, Email: iidariko.shimane-u.ac.jp

M. Oka, R. Kozako, H. Iida, Synlett, 2021, 32, 1227-1230.

DOI: 10.1055/a-1520-9916 (free Supporting Information)


Abstract

The combination of a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions at room temperature. The the biomimetic flavin catalyst enables the transfer of electrons from the iodine forming the basis for a green oxidative synthesis of disulfides from thiols.

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riboflavin tetraacetate



Key Words

aerobic oxidation, thiols, disulfides, flavins, organocatalysis, green chemistry


ID: J72-Y2021