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Title: Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction
Authors: Stevanović, Dragana
Bugarinović, Jovana
Pešić, Marko
Todosijević A.
Bogdanovic, Goran A.
Damljanović, Ivan
Issue Date: 2021
Abstract: A simple protocol has been developed for the chemoselective synthesis of ferrocene-containing Rauhut-Currier adducts from 1-ferrocenyl-2-nitroethene and vinyl ketones using 20 mol% of triphenylphosphine. Multifunctional ferrocene derivatives were obtained in moderate to high yields (51-92%) by the coupling between the α-position of vinyl ketones and the β-position of the nitroalkene. The study of the Rauhut-Currier reaction under the described conditions showed that the strong electron-donating group at the β-position of nitroalkenes plays a significant role in the reaction outcome due to prevention of polymerization and stabilization of the zwitterionic intermediate. Additionally, a preparative synthesis of 4-ferrocenyl-3-methylene-5-nitropentan-2-one was carried out and its synthetic transformations showed easy conversion to other useful building blocks. This journal is
Type: article
DOI: 10.1039/d1ra07619a
SCOPUS: 2-s2.0-85120520260
Appears in Collections:Faculty of Science, Kragujevac

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