Origin of Octafluorocyclopentene Polyelectrophilicity.

J Am Chem Soc

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.

Published: February 2024

Octafluorocyclopentene (OFCP) has found utility as a polyelectrophile in substitution cascades that form complex macrocyclic compounds. The Harran group synthesis of macrocyclic polypeptides depends on OFCP as a linker, combining with four different nucleophilic units of a polypeptide. We report a computational investigation of the origins of OFCP reactivity and a rationale for controlled mono-, di-, tri-, and tetrasubstitution of fluoride ions by heteroatomic nucleophiles. The roles of inductive, negative hyperconjugative, and resonance electron-donation by fluoride substituents are explored for the reaction of OFCP, less-fluorinated analogues, and common electrophilic alkenes with several different nucleophiles.

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Source
http://dx.doi.org/10.1021/jacs.3c12690DOI Listing

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