Iodine‐Mediated Synthesis of Methylthio‐Substituted Catechols from Cyclohexanones

A novel and efficient I2‐mediated direct synthesis of methylthio‐substituted catechols from cyclohexanones was developed. Various cyclohexanones underwent oxygenation, methylthiolation, and dehydrogenative aromatization in one pot to form the desired products in moderate to good yields. DMSO was uti...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 361; no. 12; pp. 3008 - 3013
Main Authors Wu, Yue‐Hua, Wang, Nai‐Xing, Zhang, Tong, Yan, Zhan, Xu, Bao‐Cai, Inoa, Joan, Xing, Yalan
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.06.2019
Wiley Subscription Services, Inc
Subjects
catechol
Chemistry
Chemistry, Applied
Chemistry, Organic
Cyclohexanone
Dehydrogenation
Iodine
methylthiolation
one pot reaction
Oxygenation
Physical Sciences
Reaction mechanisms
Science & Technology
Substitutes
Synthesis
synthetic methods
OXIDATION
one pot reaction
P-ARYLTHIO CINNAMIDES
SULFIDES
VINYLARENES
ADHESION MOLECULE-1 INTERACTION
FUNCTIONALIZATION
catechol
cyclohexanone
methylthiolation
COUPLING REACTION
INHIBITORS
ANTAGONISTS
THIOETHERS
synthetic methods
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Summary:A novel and efficient I2‐mediated direct synthesis of methylthio‐substituted catechols from cyclohexanones was developed. Various cyclohexanones underwent oxygenation, methylthiolation, and dehydrogenative aromatization in one pot to form the desired products in moderate to good yields. DMSO was utilized as the solvent, oxygen source, and methylthiolation agent. A possible reaction mechanism is proposed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900069