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Synlett 2021; 32(12): 1227-1230
DOI: 10.1055/a-1520-9916
DOI: 10.1055/a-1520-9916
letter
Green Aerobic Oxidation of Thiols to Disulfides by Flavin–Iodine Coupled Organocatalysis
This work was supported in part by JSPS/MEXT KAKENHI [Grant-in-Aid for Scientific Research (C), No. 19K05617] and by the Electric Technology Research Foundation of Chugoku.
Abstract
Coupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1520-9916.
- Supporting Information
Publication History
Received: 22 April 2021
Accepted: 31 May 2021
Accepted Manuscript online:
31 May 2021
Article published online:
14 June 2021
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For the selected examples, see:
For the selected examples, see:
For reviews, see:
Similar neutral riboflavin derivatives have been applied in the oxidation of thiols without photoirradiation or an iodine catalyst, but the reaction rate was very slow; see: