A Method for the Reductive Scission of Heterocyclic Thioethers

A mild, chemoselective, and generally high-yielding method for the reductive scission of heterocyclic thioethers is described. Suitable heterocycles have a thioether substituent at the 2-position relative to a ring heteroatom. The convenient and straightforward method is demonstrated with reactants...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 23; pp. 6232 - 6235
Main Authors Graham, Thomas H, Liu, Wensheng, Shen, Dong-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.12.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Sulfides - chemistry
GENERAL-SYNTHESIS
REAGENTS
EFFICIENT PREPARATION
ARYL HALIDES
COUPLING REACTION
PYRIMIDINES
THIOL ESTERS
ALDEHYDES
RECEPTOR ANTAGONIST
ETHANETHIOL ESTERS
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Summary:A mild, chemoselective, and generally high-yielding method for the reductive scission of heterocyclic thioethers is described. Suitable heterocycles have a thioether substituent at the 2-position relative to a ring heteroatom. The convenient and straightforward method is demonstrated with reactants which are not compatible with the standard Raney nickel conditions such as sulfides, sulfones, and thiophenes. In addition, benzyl esters, benzyl amides, and benzyl carbamates are tolerated by the reductive reaction conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2026813