Substitution of Fluorine in M[C6F5BF3] with Organolithium Compounds: Distinctions between O- and N-Nucleophiles | Sciact - CRIS-система Института катализа

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	G.K. Boreskov Institute of Catalysis, SB RAS, Acad. Lavrentjev Ave. 5, Novosibirsk, 630090, Russian Federation
2	Novosibirsk State University, Pirogova str. 2, Novosibirsk, 630090, Russian Federation
3	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, SB RAS, Acad. Lavrentjev Ave. 9, Novosibirsk, 630090, Russian Federation

Информация о финансировании (1)

Российский фонд фундаментальных исследований

16-29-10762

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].

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 CAPlusCA PMID OpenAlex

Полный текст от издателя

Поступила в редакцию:	12 дек. 2016 г.
Принята к публикации:	28 мар. 2017 г.
Опубликована в печати:	12 апр. 2017 г.
Опубликована online:	12 апр. 2017 г.

Web of science:	WOS:000407576500001
Scopus:	2-s2.0-85020535436
РИНЦ:	29755190
Chemical Abstracts:	2017:1102450
Chemical Abstracts (print):	167:267503
PMID (PubMed):	28503205
OpenAlex:	W2607286385

БД	Цитирований
Web of science	7
Scopus	6
РИНЦ	6
OpenAlex	6