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Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction

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2021
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Authors
Stevanović, Dragana D.
Bugarinović, Jovana
Pešić, Marko
Todosijević, Anka
Bogdanović, Goran A.
Damljanović, Ivan S.
Article (Published version)
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© The Royal Society of Chemistry
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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.
Source:
RSC Advances, 2021, 11, 57, 36208-36214
Funding / projects:
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200122 (University of Kragujevac, Faculty of Science) (RS-200122)
Note:
  • Supplementary material: https://vinar.vin.bg.ac.rs/handle/123456789/10085
  • Dataset: https://vinar.vin.bg.ac.rs/handle/123456789/10086
Related info:
  • Referenced by
    https://vinar.vin.bg.ac.rs/handle/123456789/10085
  • Referenced by
    https://vinar.vin.bg.ac.rs/handle/123456789/10086
  • Referenced by
    https://dx.doi.org/10.5517/ccdc.csd.cc28c0g4

DOI: 10.1039/D1RA07619A

ISSN: 2046-2069

WoS: 000716595300001

Scopus: 2-s2.0-85120520260
[ Google Scholar ]
URI
https://vinar.vin.bg.ac.rs/handle/123456789/10070
Collections
  • Radovi istraživača
Institution/Community
Vinča
TY  - JOUR
AU  - Stevanović, Dragana D.
AU  - Bugarinović, Jovana
AU  - Pešić, Marko
AU  - Todosijević, Anka
AU  - Bogdanović, Goran A.
AU  - Damljanović, Ivan S.
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10070
AB  - 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.
T2  - RSC Advances
T1  - Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction
VL  - 11
IS  - 57
SP  - 36208
EP  - 36214
DO  - 10.1039/D1RA07619A
ER  - 
@article{
author = "Stevanović, Dragana D. and Bugarinović, Jovana and Pešić, Marko and Todosijević, Anka and Bogdanović, Goran A. and Damljanović, Ivan S.",
year = "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.",
journal = "RSC Advances",
title = "Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction",
volume = "11",
number = "57",
pages = "36208-36214",
doi = "10.1039/D1RA07619A"
}
Stevanović, D. D., Bugarinović, J., Pešić, M., Todosijević, A., Bogdanović, G. A.,& Damljanović, I. S.. (2021). Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction. in RSC Advances, 11(57), 36208-36214.
https://doi.org/10.1039/D1RA07619A
Stevanović DD, Bugarinović J, Pešić M, Todosijević A, Bogdanović GA, Damljanović IS. Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction. in RSC Advances. 2021;11(57):36208-36214.
doi:10.1039/D1RA07619A .
Stevanović, Dragana D., Bugarinović, Jovana, Pešić, Marko, Todosijević, Anka, Bogdanović, Goran A., Damljanović, Ivan S., "Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction" in RSC Advances, 11, no. 57 (2021):36208-36214,
https://doi.org/10.1039/D1RA07619A . .

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