Synthesis 2012; 44(12): 1818-1824
DOI: 10.1055/s-0031-1290945
special topic
© Georg Thieme Verlag Stuttgart · New York

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

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
› Author Affiliations
Further Information

Publication History

Received: 03 March 2012

Accepted: 07 March 2012

Publication Date:
04 May 2012 (eFirst)

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.

Supporting Information

Primary Data

 
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