Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction
Authors
Stevanović, Dragana D.
Bugarinović, Jovana
Pešić, Marko

Todosijević, Anka
Bogdanović, Goran A.

Damljanović, Ivan S.

Article (Published version)
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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.
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RSC Advances, 2021, 11, 57, 36208-36214Funding / projects:
Note:
- Supplementary material: https://vinar.vin.bg.ac.rs/handle/123456789/10085
- Dataset: https://vinar.vin.bg.ac.rs/handle/123456789/10086
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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
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VinčaTY - 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 . .