Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles Full article
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Journal of Organic Chemistry
ISSN: 0022-3263 |
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| Output data | Year: 2019, Volume: 84, Number: 2, Pages: 963-972 Pages count : 10 DOI: 10.1021/acs.joc.8b02904 | ||||||
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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
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 |