ortho-Borylated trifluoroacetanilides: synthesis and fluoride ion binding properties

Issue title: Polyfunctional Organoboranes

Article type: Research Article

Authors: Hudnall, Todd W. | Bondi, James F. | Gabbaï, François P.

Affiliations: Department of Chemistry, Texas A&M University, College Station, Texas 77843, USA

Note: [] Corresponding author. E-mail: [email protected]

Abstract: The o-(pinacolboryl)trifluoroacetanilide (1) has been synthesized and structurally characterized. As indicated by NMR spectroscopy, this novel derivative reacts with fluoride to afford the corresponding fluoroborate derivative [1–F]− in which the boron-bound fluorine atom forms a hydrogen bond with the proton of the trifluoroacetamide functionality. Compound 1 reacts with KHF2 to afford the corresponding trifluoroborate derivative which has been isolated as a dibenzo-18-crown-6 potassium salt (2). The crystal structure and the 1H NMR spectrum of this salt confirm the presence of a B–F ··· H–N hydrogen bond.

Keywords: Boron, Fluoride, Hydrogen-bond

DOI: 10.1080/10241220701596753

Journal: Main Group Chemistry, vol. 5, no. 4, pp. 319-327, 2006