Cesium carbonate-promoted synthesis of aryl methyl sulfides using S-methylisothiourea sulfate under transition-metal-free conditions.
Org Biomol Chem
; 16(34): 6316-6321, 2018 08 29.
Article
em En
| MEDLINE
| ID: mdl-30128466
ABSTRACT
In the presence of cesium carbonate, an efficient synthesis of aryl methyl sulfides by the reactions of aryl halides with commercially available S-methylisothiourea sulfate is developed. This odourless and highly crystalline solid can be used as the substitute for malodorous methanethiol. The gram-scale reaction also proceeds smoothly without the use of column chromatography separation. Similarly, 2-(dimethylamino)ethylthio and cyclopropylmethylthio groups can be easily introduced into the aromatic rings from the corresponding S-[2-(dimethylamino)ethyl]isothiourea dihydrochloride and S-cyclopropylmethylisothiourea hydrobromide. The possible reaction mechanism is proposed. It is believed that this route to aryl alkyl sulfides is well competitive with currently known methods due to its wide substrate scope, excellent yields, easy operation and transition-metal-free conditions.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2018
Tipo de documento:
Article