Literature DB >> 21510616

Ti(O-i-Pr)4/Me3SiCl/Mg-mediated reductive cleavage of sulfonamides and sulfonates to amines and alcohols.

Noriaki Shohji1, Tsuyoshi Kawaji, Sentaro Okamoto.   

Abstract

A low-valent titanium generated in situ from Ti(O-i-Pr)(4), Me(3)SiCl, 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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Year:  2011        PMID: 21510616     DOI: 10.1021/ol200740r

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides.

Authors:  Paul T Marcyk; Latisha R Jefferies; Deyaa I AbuSalim; Maren Pink; Mu-Hyun Baik; Silas P Cook
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-15       Impact factor: 15.336

2.  Practical and Sustainable Synthesis of Optically Pure Levocabastine, a H₁ Receptor Antagonist.

Authors:  Sung Kwon Kang; Dong Hyuk Nam; Jaeseung Ahn; Jaemin Lee; Jaehoon Sim; Jeeyeon Lee; Young-Ger Suh
Journal:  Molecules       Date:  2017-11-15       Impact factor: 4.411

3.  Reduction of Substituted Benzo-Fused Cyclic Sulfonamides with Mg-MeOH: An Experimental and Computational Study.

Authors:  Aisha Khalifa; Robert Redmond; Goar Sánchez-Sanz; Paul Evans
Journal:  J Org Chem       Date:  2022-09-01       Impact factor: 4.198

  3 in total

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