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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 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

Funding (1)

1 Russian Foundation for Basic Research 16-29-10762

Abstract: 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].
Cite: 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 ANCAN PMID OpenAlex
Files: Full text from publisher
Dates:
Submitted: Dec 12, 2016
Accepted: Mar 28, 2017
Published print: Apr 12, 2017
Published online: Apr 12, 2017
Identifiers:
Web of science: WOS:000407576500001
Scopus: 2-s2.0-85020535436
Elibrary: 29755190
Chemical Abstracts: 2017:1102450
Chemical Abstracts (print): 167:267503
PMID: 28503205
OpenAlex: W2607286385
Citing:
DB Citing
Web of science 8
Scopus 6
Elibrary 7
OpenAlex 6
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