Metal-Free Photocatalytic Aerobic Oxidation of Thiols to Disulfides in Batch and Continuous-Flow

Disulfides represent significant molecular and structural features in various biologically active compounds and fine chemicals. Therefore, the development of mild, efficient and sustainable methods to access disulfides is of great importance. Here, we describe the development of a mild metal‐free ph...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-07, Vol.357 (10), p.2180-2186
Main Authors: Talla, Ali, Driessen, Brian, Straathof, Natan J. W., Milroy, Lech-Gustav, Brunsveld, Luc, Hessel, Volker, Noël, Timothy
Format: Article
Language:English
Subjects:
aerobic oxidation
Catalysis
disulfide bond formation
Disulfides
flow chemistry
Hormones
Oxidation
Photocatalysis
photoredox catalysis
Reaction time
Synthesis
Thiols
visible light
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Disulfides represent significant molecular and structural features in various biologically active compounds and fine chemicals. Therefore, the development of mild, efficient and sustainable methods to access disulfides is of great importance. Here, we describe the development of a mild metal‐free photocatalytic aerobic oxidation of thiols to disulfides using Eosin Y and visible‐light irradiation. A continuous flow procedure was developed to accelerate the photocatalytic process, enabling the preparation of disulfides with high purity in a timeframe of minutes. The mildness and applicability of our method was exemplified by the flow synthesis of the cyclic peptide hormone, oxytocin, requiring only a 200 s reaction time and an efficient one‐pot batch protocol for the preparation of the therapeutic thiuram disulfide, disulfiram.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201401010