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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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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Abstract	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.
AbstractList	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. 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. magnified image 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 200s reaction time and an efficient one-pot batch protocol for the preparation of the therapeutic thiuram disulfide, disulfiram.
Author	Driessen, Brian Hessel, Volker Milroy, Lech-Gustav Brunsveld, Luc Noël, Timothy Talla, Ali Straathof, Natan J. W.
Author_xml	– sequence: 1 givenname: Ali surname: Talla fullname: Talla, Ali organization: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands – sequence: 2 givenname: Brian surname: Driessen fullname: Driessen, Brian organization: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands – sequence: 3 givenname: Natan J. W. surname: Straathof fullname: Straathof, Natan J. W. organization: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands – sequence: 4 givenname: Lech-Gustav surname: Milroy fullname: Milroy, Lech-Gustav organization: Laboratory of Chemical Biology and Institute of Complex Molecular Systems (ICMS), Department of Biomedical Engineering, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands – sequence: 5 givenname: Luc surname: Brunsveld fullname: Brunsveld, Luc organization: Laboratory of Chemical Biology and Institute of Complex Molecular Systems (ICMS), Department of Biomedical Engineering, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands – sequence: 6 givenname: Volker surname: Hessel fullname: Hessel, Volker organization: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands – sequence: 7 givenname: Timothy surname: Noël fullname: Noël, Timothy email: t.noel@tue.nl organization: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The Netherlands
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Snippet	Disulfides represent significant molecular and structural features in various biologically active compounds and fine chemicals. Therefore, the development of...
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SubjectTerms	aerobic oxidation Catalysis disulfide bond formation Disulfides flow chemistry Hormones Oxidation Photocatalysis photoredox catalysis Reaction time Synthesis Thiols visible light
Title	Metal-Free Photocatalytic Aerobic Oxidation of Thiols to Disulfides in Batch and Continuous-Flow
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