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Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles. / Peshkov, Roman Yu; Wang, Chunyan; Panteleeva, Elena V. и др.

в: Journal of Organic Chemistry, Том 84, № 2, 18.01.2019, стр. 963-972.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Peshkov, RY, Wang, C, Panteleeva, EV, Rybalova, TV & Tretyakov, EV 2019, 'Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles', Journal of Organic Chemistry, Том. 84, № 2, стр. 963-972. https://doi.org/10.1021/acs.joc.8b02904

APA

Peshkov, R. Y., Wang, C., Panteleeva, E. V., Rybalova, T. V., & Tretyakov, E. V. (2019). Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles. Journal of Organic Chemistry, 84(2), 963-972. https://doi.org/10.1021/acs.joc.8b02904

Vancouver

Peshkov RY, Wang C, Panteleeva EV, Rybalova TV, Tretyakov EV. Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles. Journal of Organic Chemistry. 2019 янв. 18;84(2):963-972. doi: 10.1021/acs.joc.8b02904

Author

Peshkov, Roman Yu ; Wang, Chunyan ; Panteleeva, Elena V. и др. / Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles. в: Journal of Organic Chemistry. 2019 ; Том 84, № 2. стр. 963-972.

BibTeX

@article{d97d367650954e3bb096b697e26b3bbf,
title = "Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles",
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.",
keywords = "TEREPHTHALONITRILE DIANION, 2-ELECTRON REDUCTION, CHEMISTRY, ARENES, DIPHENYLHYDROXYMETHYLATION, DIPHENYLOXYMETHYLATION, QUINAZOLINES, ACTIVATION, PRODUCTS, KETYLS",
author = "Peshkov, {Roman Yu} and Chunyan Wang and Panteleeva, {Elena V.} and Rybalova, {Tatyana V.} and Tretyakov, {Evgeny V.}",
note = "Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",
year = "2019",
month = jan,
day = "18",
doi = "10.1021/acs.joc.8b02904",
language = "English",
volume = "84",
pages = "963--972",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "2",

}

RIS

TY - JOUR

T1 - Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles

AU - Peshkov, Roman Yu

AU - Wang, Chunyan

AU - Panteleeva, Elena V.

AU - Rybalova, Tatyana V.

AU - Tretyakov, Evgeny V.

N1 - Publisher Copyright: Copyright © 2018 American Chemical Society.

PY - 2019/1/18

Y1 - 2019/1/18

N2 - 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.

AB - 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.

KW - TEREPHTHALONITRILE DIANION

KW - 2-ELECTRON REDUCTION

KW - CHEMISTRY

KW - ARENES

KW - DIPHENYLHYDROXYMETHYLATION

KW - DIPHENYLOXYMETHYLATION

KW - QUINAZOLINES

KW - ACTIVATION

KW - PRODUCTS

KW - KETYLS

UR - http://www.scopus.com/inward/record.url?scp=85060050845&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b02904

DO - 10.1021/acs.joc.8b02904

M3 - Article

C2 - 30583695

AN - SCOPUS:85060050845

VL - 84

SP - 963

EP - 972

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 2

ER -

ID: 18170405