4.8 Article

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

Journal

ORGANIC LETTERS
Volume 13, Issue 10, Pages 2626-2629

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol200740r

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT) [22550103]
  2. Grants-in-Aid for Scientific Research [22550103] Funding Source: KAKEN

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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.

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