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Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles Научная публикация

Журнал Journal of Organic Chemistry
ISSN: 0022-3263
Вых. Данные Год: 2019, Том: 84, Номер: 2, Страницы: 963-972 Страниц : 10 DOI: 10.1021/acs.joc.8b02904
Авторы Peshkov Roman Yu 1,2 , Wang Chunyan 2,3 , Panteleeva Elena V. 1,2 , Rybalova Tatyana V. 1,2 , Tretyakov Evgeny V. 1,2
Организации
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

Реферат: 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.
Библиографическая ссылка: 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
Даты:
Опубликована online: 24 дек. 2018 г.
Опубликована в печати: 18 янв. 2019 г.
Идентификаторы БД:
Web of science: WOS:000456632800047
Scopus: 2-s2.0-85060050845
РИНЦ: 38651862
OpenAlex: W2905645398
Цитирование в БД:
БД Цитирований
Web of science 5
Scopus 3
РИНЦ 2
OpenAlex 4
Альметрики: