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

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

Journal

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Output data

Year: 2017, Volume: 13, Pages: 703-713 Pages count : 11 DOI: 10.3762/bjoc.13.69

Tags

C-nucleophile; NMR spectroscopy; nucleophilic substitution; pentafluorophenyltrifluoroborate

Authors

Shabalin Anton Yu. ^1,2 , Adonin Nicolay Yu. ^1,2 , Bardin Vadim V. ^2,3

Affiliations

1	(Данные Web of science) SB RAS, GK Boreskov Inst Catalysis, Acad Lavrentjev Ave 5, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova Str 2, Novosibirsk 630090, Russia
3	(Данные Web of science) SB RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem, Acad Lavrentjev Ave 9, Novosibirsk 630090, Russia

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-NuC(6)F(4)BF(3)].

Shabalin A.Y. , Adonin N.Y. , Bardin V.V.
Substitution of fluorine in M[C6F5BF3] with organolithium compounds: distinctions between O- and N-nucleophiles

Beilstein Journal of Organic Chemistry. 2017. V.13. P.703-713. DOI: 10.3762/bjoc.13.69 WOS Scopus РИНЦ

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Published online:

Apr 12, 2017

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