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

Murphy, John A. and Zhou, Sheng-Ze and Jolly, Phillip I and Fleary-Roberts, Nadia and O'Sullivan, Steven and Doni, Eswararao (2012) Reactions of triflate esters and triflamides with an organic neutral super-electron-donor. Organic and Biomolecular Chemistry, 10. pp. 5807-5810. ISSN 1477-0520

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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.