Synthesis of a Wide Range of Thioethers by Indium Triiodide Catalyzed Direct Coupling between Alkyl Acetates and Thiosilanes

An indium triiodide-catalyzed substitution of the acetoxy group in alkyl acetates with thiosilanes provides access to a variety of thioethers. The method is efficient for a wide scope of acetates such as primary alkyl, secondary alkyl, tertiary alkyl, allylic, benzylic, and propargylic acetates.

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 7; pp. 1846 - 1849
Main Authors Nishimoto, Yoshihiro, Okita, Aya, Yasuda, Makoto, Baba, Akio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.04.2012
Amer Chemical Soc
Subjects
Acetates - chemistry
Catalysis
Chemistry
Chemistry, Organic
Indium - chemistry
Iodine Compounds - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Silanes - chemistry
Sulfides - chemical synthesis
Sulfides - chemistry
THIOLS
TRIBROMIDE
KETENE SILYL ACETALS
DIRECT SUBSTITUTION
B(C6F5)-CATALYZED ALLYLATION
ENOL ACETATES
PROPARGYLIC ALCOHOLS
ARYL SULFIDES
OXIDATION-REDUCTION CONDENSATION
CARBOXYLIC-ACIDS
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Summary:An indium triiodide-catalyzed substitution of the acetoxy group in alkyl acetates with thiosilanes provides access to a variety of thioethers. The method is efficient for a wide scope of acetates such as primary alkyl, secondary alkyl, tertiary alkyl, allylic, benzylic, and propargylic acetates.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300450j