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

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

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.

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

Published online:	Dec 24, 2018
Published print:	Jan 18, 2019

Web of science	WOS:000456632800047
Scopus	2-s2.0-85060050845
Elibrary	38651862
OpenAlex	W2905645398