Tandem Nucleophilic Addition/Fragmentation of Vinylogous Acyl Nonaflates for the Synthesis of Functionalized Alkynes, with New Mechanistic Insight

Vinylogous acyl nonaflates, like the corresponding triflates, are subject to nucleophile-triggered fragmentation as part of a tandem process for generating functionalized alkynes. Advantages to the use of nonaflates in lieu of triflates include cost and stability. Computational analysis supports a p...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 44; no. 12; pp. 1818 - 1824
Main Authors Batsomboon, Paratchata, Gold, Brian A., Alabugin, Igor V., Dudley, Gregory B.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.06.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tandem reaction
solvent effects
GENERAL-SYNTHESIS
CYCLOADDITIONS
alkynes
CONDENSATION
CARBON BOND-CLEAVAGE
DECARBOXYLATIVE ELIMINATION
RULES
nucleophilic addition
fragmentation
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Summary:Vinylogous acyl nonaflates, like the corresponding triflates, are subject to nucleophile-triggered fragmentation as part of a tandem process for generating functionalized alkynes. Advantages to the use of nonaflates in lieu of triflates include cost and stability. Computational analysis supports a postulated fragmentation mechanism involving a closed (cyclic) transition state with concerted extrusion of lithium sulfonate.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1290945