Substitution of fluorine in M[C₆F₅BF₃] with organolithium compounds: distinctions between O- and N-nucleophiles

• Anton Yu. Shabalin,
• Nicolay Yu. Adonin and
• Vadim V. Bardin

Beilstein J. Org. Chem. 2017, 13, 703–713, doi:10.3762/bjoc.13.69

• atom with the fluorine atoms of the BF3 group. This differs from the previously reported substitution in K[C6F5BF3] by O- and N-nucleophiles that did not produce K[2-NuC6F4BF3]. Keywords: C-nucleophile; NMR spectroscopy; nucleophilic substitution; pentafluorophenyltrifluoroborate; Introduction

• are expensive. An alternative approach is based on modification of easily available potassium pentafluorophenyltrifluoroborate (1-K) and we carried out systematic research in this field. Thus, K[C6F5BF3] was converted into K[2,3,4,5-C6HF4BF3] using NiCl2·6H2O and Zn in the presence of bpy in aprotic

• and PhLi were prepared from lithium and MeI or PhBr, they contain the corresponding lithium halides. It follows that the precipitate consists of KI and KBr, respectively, and the actual boron-containing reactant is lithium pentafluorophenyltrifluoroborate (1-Li). Independently, Li[C6F5BF3] was