TY - JOUR

T1 - Substitution of fluorine in M[C6F5BF3] with organolithium compounds

T2 - Distinctions between O- and N-nucleophiles

AU - Shabalin, Anton Yu

AU - Adonin, Nicolay Yu

AU - Bardin, Vadim V.

PY - 2017/4/12

Y1 - 2017/4/12

N2 - Borates M[C6F5BF3] (M = K, Li, Bu4N) react with organolithium compounds, RLi (R = Me, Bu, Ph), in 1,2-dimethoxyethane or diglyme to give M[4-RC6F4BF3] and M[2-RC6F4BF3]. When R is Me or Bu, the nucleophilic substitution of the fluorine atom at the para position to boron is the predominant route. When R = Ph, the ratio M[4-RC6F4BF3]/M[2-RC6F4BF3] is ca. 1: 1. Substitution of the fluorine atom at the ortho position to boron is solely caused by the coordination of RLi via the lithium 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].

AB - Borates M[C6F5BF3] (M = K, Li, Bu4N) react with organolithium compounds, RLi (R = Me, Bu, Ph), in 1,2-dimethoxyethane or diglyme to give M[4-RC6F4BF3] and M[2-RC6F4BF3]. When R is Me or Bu, the nucleophilic substitution of the fluorine atom at the para position to boron is the predominant route. When R = Ph, the ratio M[4-RC6F4BF3]/M[2-RC6F4BF3] is ca. 1: 1. Substitution of the fluorine atom at the ortho position to boron is solely caused by the coordination of RLi via the lithium 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].

KW - C-nucleophile

KW - NMR spectroscopy

KW - Nucleophilic substitution

KW - Pentafluorophenyltrifluoroborate

UR - http://www.scopus.com/inward/record.url?scp=85020535436&partnerID=8YFLogxK

U2 - 10.3762/bjoc.13.69

DO - 10.3762/bjoc.13.69

M3 - Article

C2 - 28503205

AN - SCOPUS:85020535436

VL - 13

SP - 703

EP - 713

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -