Issue 30, 2012

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

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 triflates has been seen with other reagents and by more than one mechanism, the deprotection of alkyl triflates is a new reaction. Studies with 18O labelled DMF indicate that the C–O bond 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.

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

Supplementary files

Article information

Article type
Communication
Submitted
15 jan 2012
Accepted
20 feb 2012
First published
22 feb 2012

Org. Biomol. Chem., 2012,10, 5807-5810

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

P. I. Jolly, N. Fleary-Roberts, S. O'Sullivan, E. Doni, S. Zhou and J. A. Murphy, Org. Biomol. Chem., 2012, 10, 5807 DOI: 10.1039/C2OB25116G

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