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

Paratchata Batsomboon; Brian A. Gold; Igor V. Alabugin; Gregory B. Dudley

doi:10.1055/s-0031-1290945

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(12): 1818-1824
DOI: 10.1055/s-0031-1290945

special topic

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

Authors

Paratchata Batsomboon

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA, Fax: +1(850)6448281 eMail: gdudley@chem.fsu.edu
Brian A. Gold

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA, Fax: +1(850)6448281 eMail: gdudley@chem.fsu.edu
Igor V. Alabugin

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA, Fax: +1(850)6448281 eMail: gdudley@chem.fsu.edu
Gregory B. Dudley*

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA, Fax: +1(850)6448281 eMail: gdudley@chem.fsu.edu

Abstract

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Abstract

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.

Key words

alkynes - fragmentation - nucleophilic addition - solvent effects - tandem reaction

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Referenzen

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