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

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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Veröffentlicht in:Organic letters 2011-05, Vol.13 (10), p.2626-2629
Hauptverfasser: Shohji, Noriaki, Kawaji, Tsuyoshi, Okamoto, Sentaro
Format: Artikel
Sprache:eng
Schlagworte:
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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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200740r