Ligand-Free Copper(I)-Mediated Cross-Coupling Reactions of Organostannanes with Sulfur Electrophiles

The synthesis of aryl thioether through the cross-coupling of C–S bond is a highly attractive area of research due to the prevalence of aryl thioether in bioactive natural products, functional materials, agrochemicals, and pharmaceutically active compounds. Herein, we report a ligand-free Cu­(I) med...

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Published inJournal of organic chemistry Vol. 85; no. 18; pp. 11942 - 11951
Main Authors Zhu, Feng, Chen, Zhenhao, Walczak, Maciej A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.09.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
ROOM-TEMPERATURE
THIOLS
ORGANOBORONIC ACIDS
CATALYZED C-S
ARYL HALIDES
TE BOND
ARYLBORONIC ACIDS
SULFENYL CHLORIDES
DISULFIDES
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Summary:The synthesis of aryl thioether through the cross-coupling of C–S bond is a highly attractive area of research due to the prevalence of aryl thioether in bioactive natural products, functional materials, agrochemicals, and pharmaceutically active compounds. Herein, we report a ligand-free Cu­(I) mediated electrophilic thiolation of organostannanes with sulfur electrophiles. A selective transfer of alkyl groups was achieved in reactions with alkyl carbastannatranes affording congested thioethers. This study offers a unified method to access diaryl and aryl alkyl thioethers and was demonstrated in the context of late-stage modifications..
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01399