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Mendeleev Communications, 2025, Volume 35, Issue 4, Pages 461–463
DOI: https://doi.org/10.71267/mencom.7701
(Mi mendc6260)
 

Communications

Asymmetric Friedel–Crafts alkylation of indoles with β-nitrostyrenes catalyzed by a chiral NiII complex based on (S)-(2-aminomethyl)pyrrolidine and 3,5-di-tert-butylsalicylaldehyde

E. V. Rozhkovab, N. V. Stoletovaa, A. V. Bachinskiya, M. M. Ilyina, V. I. Maleeva, V. A. Larionova

a A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119334 Moscow, Russian Federation
b Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation
References:
Abstract: μ-(Acetato)nickel(II) complex with Schiff base of (S)-(2-aminomethyl)pyrrolidine and 3,5-di-tert-butyl-2-hydroxybenzaldehyde as the chiral ligand was tested in the asymmetric Friedel–Crafts alkylation of indoles with β-nitrostyrenes. The reactions catalyzed by 5 mol% of the complex provided the corresponding 3-(1-aryl-2-nitroethyl)indoles with up to 98% yields and up to 69% ee values.
Keywords: asymmetric Friedel–Crafts alkylation, indoles, β-nitrostyrenes, chiral nickel(II) complex, Lewis acids.
Funding agency Grant number
Russian Science Foundation 20-13-00155
Received: 02.12.2024
Accepted: 05.02.2025
Published: 21.05.2025
Bibliographic databases:
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (1.3 Mb)


Citation: E. V. Rozhkov, N. V. Stoletova, A. V. Bachinskiy, M. M. Ilyin, V. I. Maleev, V. A. Larionov, “Asymmetric Friedel–Crafts alkylation of indoles with β-nitrostyrenes catalyzed by a chiral NiII complex based on (S)-(2-aminomethyl)pyrrolidine and 3,5-di-tert-butylsalicylaldehyde”, Mendeleev Commun., 35:4 (2025), 461–463
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