Oxidative coupling of N-hydroxyphthalimide with toluene

Oxidative coupling of N-hydroxyphthalimide with toluene Full article

Journal

Russian Journal of General Chemistry
ISSN: 1070-3632 , E-ISSN: 1608-3350

Output data

Year: 2014, Volume: 84, Number: 11, Pages: 2084-2087 Pages count : 4 DOI: 10.1134/s1070363214110061

Authors

Terent’ev A.O. ¹ , Krylov I.B. ¹ , Lipatnikov A.D. ¹

Affiliations

1	Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

Oxidative C-O-coupling of N-hydroxyphthalimide (NHPI) with toluene was studied. The reaction occurred in different organic solvents with a wide range of oxidants, such as (NH4)2Ce(NO3)6, PhI(OAc)2, KMnO4, Mn(OAc)3·2H2O, Pb(OAc)4, and Co(OAc)2/O2, to afford N-benzyloxyphthalimide in yield of 11–75%. Phthalimide-N-oxyl radicals, generated under the reaction conditions, could eliminate the hydrogen atom from the benzyl fragment of alkylarene at room temperature. Probably, formation of the product of the oxidative coupling occurred via recombination of benzyl and phthalimide-N-oxyl radicals.

Terent’ev A.O. , Krylov I.B. , Lipatnikov A.D.
Oxidative coupling of N-hydroxyphthalimide with toluene
Russian Journal of General Chemistry. 2014. V.84. N11. P.2084-2087. DOI: 10.1134/s1070363214110061 WOS Scopus OpenAlex

≡ Web of science:	WOS:000346494400006
≡ Scopus:	2-s2.0-84918831738
≡ OpenAlex:	W2460265601