C-F Bond Activation with an Apparently Benign Ethynyl Dithiocarbamate, and Subsequent Fluoride Transfer Reactions

A recent trend in the activation of small molecules and enthalpically strong bonds is the use of non-metal activators. Nucleophilic aromatic substitutions can as well be achieved in good yields with the electron-poor 1-chloro-2,4-dinitrobenzene. Additionally, benzyl mesylate, tosylate, and bromide were also successfully converted to their fluorinated counterparts at a higher temperature. Lastly, the fluorine anion can even be transferred to secondary alkyl triflate, and primary and secondary alkyl iodides, although these transformations require higher temperatures and longer times, which affect their yields. The selective para C-F activation of the electrophilic pentafluoropyridine yields a cyclic adduct capable of transferring nucleophilic fluoride to various substrates.