Ti(O-i-Pr)4/Me3SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols

A low-valent titanium generated in situ from Ti(O-i-Pr)4, Me3SiCl, and Mg powder in THF reacted with aryl- and alkyl-sulfonamides of aryl and alkyl amines in a reductive N–S/S–O/S–C bond cleaving pathway to provide the corresponding amines and hydrocarbons (and thiols) derived from the sulfonyl moie...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 10; pp. 2626 - 2629
Main Authors Shohji, Noriaki, Kawaji, Tsuyoshi, Okamoto, Sentaro
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 20.05.2011
Subjects
Alcohols - chemistry
Amines - chemical synthesis
Amines - chemistry
Catalysis
Combinatorial Chemistry Techniques
Magnesium - chemistry
Molecular Structure
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
Sulfonamides - chemistry
Titanium - chemistry
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Summary:A low-valent titanium generated in situ from Ti(O-i-Pr)4, Me3SiCl, and Mg powder in THF reacted with aryl- and alkyl-sulfonamides of aryl and alkyl amines in a reductive N–S/S–O/S–C bond cleaving pathway to provide the corresponding amines and hydrocarbons (and thiols) derived from the sulfonyl moiety. The reagent could also cleave sulfonates to the corresponding alcohols.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol200740r