Ring-opening/annulation reaction of cyclopropyl ethanols: concise access to thiophene aldehydes via C-S bond formation

The synthesis of thiophene aldehydes from easily available cyclopropyl ethanol derivatives and potassium sulfide has been developed. This novel one-pot procedure achieves double C-S bond formation via the cleavage of C-C bonds. This transformation shows good functional group tolerance under mild rea...

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Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 21; pp. 3705 - 3709
Main Authors Wang, Ting, An, Zhenyu, Qi, Zhenjie, Zhuang, Daijiao, Chang, Aosheng, Yang, Yunxia, Yan, Rulong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.11.2019
Royal Society of Chemistry
Subjects
Aldehydes
Bonding
Chemical reactions
Chemistry
Chemistry, Organic
Crystallography
Ethanol
Functional groups
Organic chemistry
Organic compounds
Physical Sciences
Potassium
Science & Technology
Sulfide
TRISULFUR RADICAL-ANION
ELEMENTAL SULFUR
ORGANOMERCURIALS
FACILE SYNTHESIS
O-HALONITROBENZENES
3-COMPONENT
ALKYNES
DERIVATIVES
REDOX CONDENSATION REACTION
SULFIDE
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Summary:The synthesis of thiophene aldehydes from easily available cyclopropyl ethanol derivatives and potassium sulfide has been developed. This novel one-pot procedure achieves double C-S bond formation via the cleavage of C-C bonds. This transformation shows good functional group tolerance under mild reaction conditions. Moreover, DMSO acts as the solvent and mild oxidant simultaneously in this reaction.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo01014a