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

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 deprotecti...

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Published inOrganic & biomolecular chemistry Vol. 10; no. 30; pp. 5807 - 5810
Main Authors Jolly, Phillip I., Fleary-Roberts, Nadia, O'Sullivan, Steven, Doni, Eswararao, Zhou, Shengze, Murphy, John A.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.08.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ELECTROSYNTHESIS
ALKYL
REDUCTIVE CLEAVAGE
SULFONAMIDES
ARYL IODIDES
DEPROTECTION
COMBINATION
DERIVATIVES
PALLADIUM-CATALYZED AMINATION
TOLUENESULFONATES
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Summary: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 O-18 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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25116g