Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles

Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles

A simple, efficient, and practical sulfenylation at the C2 position of <i>N</i>-tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of <i>N</i>-tosylindoles with BuLi and <i>S</i>-alkyl, and <i>S</i>-a...

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Main Authors: Justyna Doroszuk, Mateusz Musiejuk, Bartosz Jędrzejewski, Juliusz Walczak, Dariusz Witt
Format: Article
Language:English
Published: MDPI AG 2020-10-01
Series:Materials
Subjects:
indoles
sulfides
thiotosylates
sulfenylation
sulfenylindoles
Online Access:https://www.mdpi.com/1996-1944/13/20/4492
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spelling doaj-e6f6072df9064c9da1b2d38512f6712d2020-11-25T03:35:31ZengMDPI AGMaterials1996-19442020-10-01134492449210.3390/ma13204492Convenient and Efficient Synthesis of Functionalized 2-SulfenylindolesJustyna Doroszuk0Mateusz Musiejuk1Bartosz Jędrzejewski2Juliusz Walczak3Dariusz Witt4Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandA simple, efficient, and practical sulfenylation at the C2 position of <i>N</i>-tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of <i>N</i>-tosylindoles with BuLi and <i>S</i>-alkyl, and <i>S</i>-aryl phosphorodithioates or thiotosylates to produce 2-sulfenylindoles in moderate to high yields. The presence of additional hydroxy, carboxy, or amino functionalities did not disturb the formation of products.https://www.mdpi.com/1996-1944/13/20/4492indolessulfidesthiotosylatessulfenylationsulfenylindoles
collection DOAJ
language English
format Article
sources DOAJ
author Justyna Doroszuk
Mateusz Musiejuk
Bartosz Jędrzejewski
Juliusz Walczak
Dariusz Witt
spellingShingle Justyna Doroszuk
Mateusz Musiejuk
Bartosz Jędrzejewski
Juliusz Walczak
Dariusz Witt
Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
Materials
indoles
sulfides
thiotosylates
sulfenylation
sulfenylindoles
author_facet Justyna Doroszuk
Mateusz Musiejuk
Bartosz Jędrzejewski
Juliusz Walczak
Dariusz Witt
author_sort Justyna Doroszuk
title Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
title_short Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
title_full Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
title_fullStr Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
title_full_unstemmed Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
title_sort convenient and efficient synthesis of functionalized 2-sulfenylindoles
publisher MDPI AG
series Materials
issn 1996-1944
publishDate 2020-10-01
description A simple, efficient, and practical sulfenylation at the C2 position of <i>N</i>-tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of <i>N</i>-tosylindoles with BuLi and <i>S</i>-alkyl, and <i>S</i>-aryl phosphorodithioates or thiotosylates to produce 2-sulfenylindoles in moderate to high yields. The presence of additional hydroxy, carboxy, or amino functionalities did not disturb the formation of products.
topic indoles
sulfides
thiotosylates
sulfenylation
sulfenylindoles
url https://www.mdpi.com/1996-1944/13/20/4492
work_keys_str_mv AT justynadoroszuk convenientandefficientsynthesisoffunctionalized2sulfenylindoles
AT mateuszmusiejuk convenientandefficientsynthesisoffunctionalized2sulfenylindoles
AT bartoszjedrzejewski convenientandefficientsynthesisoffunctionalized2sulfenylindoles
AT juliuszwalczak convenientandefficientsynthesisoffunctionalized2sulfenylindoles
AT dariuszwitt convenientandefficientsynthesisoffunctionalized2sulfenylindoles
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