Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

Electron-rich arenes react with aryl and alkyl disulfides in the presence of catalytic amounts of [Ir(dF(CF3)ppy)2(dtbpy)]PF6 and (NH4)2S2O8 under blue light irradiation to yield arylthiols. The reaction proceeds at room temperature and avoids the use of prefunctionalized arenes. Experimental eviden...

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Main Authors: Amrita Das, Mitasree Maity, Simon Malcherek, Burkhard König, Julia Rehbein
Format: Article
Language:English
Published: Beilstein-Institut 2018-09-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.14.228
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spelling doaj-200c0fa9faf8457c8aed8ddc983f90eb2021-03-02T11:02:24ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-09-011412520252810.3762/bjoc.14.2281860-5397-14-228Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysisAmrita Das0Mitasree Maity1Simon Malcherek2Burkhard König3Julia Rehbein4Department of Chemistry and Pharmacy, Institute of Organic Chemistry, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, GermanyDepartment of Chemistry and Pharmacy, Institute of Organic Chemistry, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, GermanyDepartment of Chemistry and Pharmacy, Institute of Organic Chemistry, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, GermanyDepartment of Chemistry and Pharmacy, Institute of Organic Chemistry, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, GermanyDepartment of Chemistry and Pharmacy, Institute of Organic Chemistry, University of Regensburg, Universitätsstraße 31, 93053 Regensburg, GermanyElectron-rich arenes react with aryl and alkyl disulfides in the presence of catalytic amounts of [Ir(dF(CF3)ppy)2(dtbpy)]PF6 and (NH4)2S2O8 under blue light irradiation to yield arylthiols. The reaction proceeds at room temperature and avoids the use of prefunctionalized arenes. Experimental evidence suggests a radical–radical cross coupling mechanism.https://doi.org/10.3762/bjoc.14.228arenesoxidationphotocatalysisthiolationvisible light
collection DOAJ
language English
format Article
sources DOAJ
author Amrita Das
Mitasree Maity
Simon Malcherek
Burkhard König
Julia Rehbein
spellingShingle Amrita Das
Mitasree Maity
Simon Malcherek
Burkhard König
Julia Rehbein
Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis
Beilstein Journal of Organic Chemistry
arenes
oxidation
photocatalysis
thiolation
visible light
author_facet Amrita Das
Mitasree Maity
Simon Malcherek
Burkhard König
Julia Rehbein
author_sort Amrita Das
title Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis
title_short Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis
title_full Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis
title_fullStr Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis
title_full_unstemmed Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis
title_sort synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2018-09-01
description Electron-rich arenes react with aryl and alkyl disulfides in the presence of catalytic amounts of [Ir(dF(CF3)ppy)2(dtbpy)]PF6 and (NH4)2S2O8 under blue light irradiation to yield arylthiols. The reaction proceeds at room temperature and avoids the use of prefunctionalized arenes. Experimental evidence suggests a radical–radical cross coupling mechanism.
topic arenes
oxidation
photocatalysis
thiolation
visible light
url https://doi.org/10.3762/bjoc.14.228
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