Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles

A simple, efficient, and practical sulfenylation at the C2 position of -tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of -tosylindoles with BuLi and -alkyl, and -aryl phosphorodithioates or thiotosylates to produce 2-sulfenylindoles in moderat...

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Published inMaterials Vol. 13; no. 20; p. 4492
Main Authors Doroszuk, Justyna, Musiejuk, Mateusz, Jędrzejewski, Bartosz, Walczak, Juliusz, Witt, Dariusz
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 10.10.2020
MDPI
Subjects
Carbon
Chromatography
Communication
indoles
Reagents
Sodium
sulfenylation
sulfenylindoles
sulfides
thiotosylates
Germany
thiotosylates
indoles
sulfenylation
sulfenylindoles
sulfides
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Abstract A simple, efficient, and practical sulfenylation at the C2 position of -tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of -tosylindoles with BuLi and -alkyl, and -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.
AbstractList A simple, efficient, and practical sulfenylation at the C2 position of N-tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of N-tosylindoles with BuLi and S-alkyl, and S-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.
A simple, efficient, and practical sulfenylation at the C2 position of N -tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of N -tosylindoles with BuLi and S -alkyl, and S -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.
A simple, efficient, and practical sulfenylation at the C2 position of -tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of -tosylindoles with BuLi and -alkyl, and -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.
Author Walczak, Juliusz
Witt, Dariusz
Musiejuk, Mateusz
Jędrzejewski, Bartosz
Doroszuk, Justyna
AuthorAffiliation Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland; juswiecz@student.pg.gda.pl (J.D.); mateusz.musiejuk@interia.eu (M.M.); barjedrz@student.pg.edu.pl (B.J.); pyrher@gmail.com (J.W.)
AuthorAffiliation_xml – name: Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland; juswiecz@student.pg.gda.pl (J.D.); mateusz.musiejuk@interia.eu (M.M.); barjedrz@student.pg.edu.pl (B.J.); pyrher@gmail.com (J.W.)
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Issue 20
Keywords thiotosylates
indoles
sulfenylation
sulfenylindoles
sulfides
Language English
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Snippet A simple, efficient, and practical sulfenylation at the C2 position of -tosylindoles under mild conditions was developed. The designed transformation is based...
A simple, efficient, and practical sulfenylation at the C2 position of N-tosylindoles under mild conditions was developed. The designed transformation is based...
A simple, efficient, and practical sulfenylation at the C2 position of N -tosylindoles under mild conditions was developed. The designed transformation is...
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Aggregation Database
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StartPage 4492
SubjectTerms Carbon
Chromatography
Communication
indoles
Reagents
Sodium
sulfenylation
sulfenylindoles
sulfides
thiotosylates
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Title Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
URI https://www.ncbi.nlm.nih.gov/pubmed/33050451
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