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

Roman Yu Peshkov, Chunyan Wang, Elena V. Panteleeva, Tatyana V. Rybalova, Evgeny V. Tretyakov

Результат исследования: Научные публикации в периодических изданияхстатья

1 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)963-972
Число страниц10
ЖурналJournal of Organic Chemistry
Том84
Номер выпуска2
DOI
СостояниеОпубликовано - 18 янв 2019

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