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...

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Bibliographic Details
Published in:Advanced synthesis & catalysis Vol. 357; no. 10; pp. 2180 - 2186
Main Authors: Talla, Ali, Driessen, Brian, Straathof, Natan J. W., Milroy, Lech-Gustav, Brunsveld, Luc, Hessel, Volker, Noël, Timothy
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 06.07.2015
WILEY‐VCH Verlag
Subjects:
aerobic oxidation
Catalysis
disulfide bond formation
Disulfides
flow chemistry
Hormones
Oxidation
Photocatalysis
photoredox catalysis
Reaction time
Synthesis
Thiols
visible light
ISSN:1615-4150, 1615-4169
Online Access:Get full text
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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.
Bibliography:European Union - No. Marie Curie CIG Grant (Flach)
Dutch Science Foundation - No. VENI Grant (No 12464)
Netherlands Organization for Scientific Research via a Gravity program - No. 024.001.035
istex:1808807D86FC95E2D2CDC9EB0C291AF8BF79B926
ark:/67375/WNG-19L8CZLH-X
ArticleID:ADSC201401010
Advanced European Research Council - No. number: 267443
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201401010