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Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles Full article

Journal Journal of Organic Chemistry
ISSN: 0022-3263
Output data Year: 2019, Volume: 84, Number: 2, Pages: 963-972 Pages count : 10 DOI: 10.1021/acs.joc.8b02904
Authors Peshkov Roman Yu 1,2 , Wang Chunyan 2,3 , Panteleeva Elena V. 1,2 , Rybalova Tatyana V. 1,2 , Tretyakov Evgeny V. 1,2
Affiliations
1 (Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia
3 (Данные Web of science) Heilongjang Univ, Xuefu Rd 74, Harbin 150080, Heilongjiang, Peoples R China

Abstract: The first example of phenylation of fluorobenzonitriles with the sodium salt of a benzonitrile radical anion in liquid ammonia is presented. The reaction regioselectivity corresponds to the ortho- and para-fluorine atom substitution in fluorobenzonitrile with the phenyl moiety of the benzonitrile radical anion and affords 2- and 4-cyanobiphenyls in 40-90% yields. 3-Methoxybenzonitrile as well as 1-cyanonaphthalene radical anions were also successfully subjected to this interaction forming 3'-methoxycyanobiphenyls and (1-naphthyl)benzonitriles, respectively. The radical anion acts as an ipso-C-nucleophile with consequent loss of the cyano group. The revealed new type of radical anion reactivity opens up the prospect of developing a general approach to fluorinated cyanobisarenes on the basis of an interaction of the cyanoarene radical anion with fluorinated substrates activated to aromatic nucleophilic substitution.
Cite: Peshkov R.Y. , Wang C. , Panteleeva E.V. , Rybalova T.V. , Tretyakov E.V.
Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles
Journal of Organic Chemistry. 2019. V.84. N2. P.963-972. DOI: 10.1021/acs.joc.8b02904 WOS Scopus РИНЦ OpenAlex
Dates:
Published online: Dec 24, 2018
Published print: Jan 18, 2019
Identifiers:
Web of science: WOS:000456632800047
Scopus: 2-s2.0-85060050845
Elibrary: 38651862
OpenAlex: W2905645398
Citing:
DB Citing
Web of science 4
Scopus 3
Elibrary 2
OpenAlex 3
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