Reactions of triflate esters and triflamides with an organic neutral super-electron-donor

John A. Murphy, Sheng-Ze Zhou, Phillip I Jolly, Nadia Fleary-Roberts, Steven O'Sullivan, Eswararao Doni

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The bis-pyridinylidene 13 converts aliphatic and aryl triflate esters to the corresponding alcohols and phenols respectively using DMF as solvent, generally in excellent yields. While the deprotection of aryl tiflates has been seen with other reagents and by more than one mechanism, the deprotection of alkyl triflates is a new reaction. Studies with 18-O labelled DMF studies indicate that the C-O bond of the triflate ester stays intact and hence it is the S-O bond that cleaves, underlining that the cleavage results from the extraordinary electron donor capability of 13. Trifluoromethanesulfonamides are converted to the parent amines in like manner, representing the first cleavage of such substrates by a ground-state organic reducing reagent.
LanguageEnglish
Pages5807-5810
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume10
DOIs
Publication statusPublished - 2012

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reagents
esters
cleavage
Esters
Electrons
Phenols
guy wires
phenols
Ground state
Amines
amines
alcohols
electrons
Alcohols
ground state
Substrates

Keywords

  • triflate esters
  • triflamides
  • bis-pyridinylidene 13
  • DMF as solvent
  • O labelled DMF

Cite this

Murphy, John A. ; Zhou, Sheng-Ze ; Jolly, Phillip I ; Fleary-Roberts, Nadia ; O'Sullivan, Steven ; Doni, Eswararao. / Reactions of triflate esters and triflamides with an organic neutral super-electron-donor. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10. pp. 5807-5810.
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Reactions of triflate esters and triflamides with an organic neutral super-electron-donor. / Murphy, John A.; Zhou, Sheng-Ze; Jolly, Phillip I; Fleary-Roberts, Nadia; O'Sullivan, Steven; Doni, Eswararao.

In: Organic and Biomolecular Chemistry, Vol. 10, 2012, p. 5807-5810.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Reactions of triflate esters and triflamides with an organic neutral super-electron-donor

AU - Murphy, John A.

AU - Zhou, Sheng-Ze

AU - Jolly, Phillip I

AU - Fleary-Roberts, Nadia

AU - O'Sullivan, Steven

AU - Doni, Eswararao

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AB - The bis-pyridinylidene 13 converts aliphatic and aryl triflate esters to the corresponding alcohols and phenols respectively using DMF as solvent, generally in excellent yields. While the deprotection of aryl tiflates has been seen with other reagents and by more than one mechanism, the deprotection of alkyl triflates is a new reaction. Studies with 18-O labelled DMF studies indicate that the C-O bond of the triflate ester stays intact and hence it is the S-O bond that cleaves, underlining that the cleavage results from the extraordinary electron donor capability of 13. Trifluoromethanesulfonamides are converted to the parent amines in like manner, representing the first cleavage of such substrates by a ground-state organic reducing reagent.

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KW - triflamides

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