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 Научная публикация

Журнал

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Вых. Данные

Год: 2017, Том: 13, Страницы: 703-713 Страниц : 11 DOI: 10.3762/bjoc.13.69

Ключевые слова

C-nucleophile; NMR spectroscopy; nucleophilic substitution; pentafluorophenyltrifluoroborate

Авторы

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

Организации

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

Полный текст от издателя

Опубликована online:

12 апр. 2017 г.

Web of science	WOS:000407576500001
Scopus	2-s2.0-85020535436
РИНЦ	29755190
OpenAlex	W2607286385