Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 May 6:17:1041-1047.
doi: 10.3762/bjoc.17.83. eCollection 2021.

Nitroalkene reduction in deep eutectic solvents promoted by BH3NH3

Chiara Faverio  1 , Monica Fiorenza Boselli  1 , Patricia Camarero Gonzalez  1 , Alessandra Puglisi  1 , Maurizio Benaglia  1
Affiliations

Nitroalkene reduction in deep eutectic solvents promoted by BH3NH3

Chiara Faverio et al. Beilstein J Org Chem. .

Abstract

Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH3NH3, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated.

Keywords: DES; alternative solvents; atom economy; nitro derivatives; reduction.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
AB-mediated reductions of nitrostyrenes 3a–h.
Scheme 2
Scheme 2
AB-mediated reductions of nitrostyrenes 1, 3a, and 3c using DESs B and D.
Scheme 3
Scheme 3
AB-mediated reductions of nitroalkenes 5a–f.
Scheme 4
Scheme 4
Recovery and recycling experiments in the AB-mediated reduction of nitrostyrene 3h to afford nitroalkane 4h.
See this image and copyright information in PMC

References

    1. Smith E L, Abbott A P, Ryder K S. Chem Rev. 2014;114(21):11060–11082. doi: 10.1021/cr300162p. - DOI - PubMed
    1. Alonso D A, Baeza A, Chinchilla R, Guillena G, Pastor I M, Ramón D J. Eur J Org Chem. 2016:612–632. doi: 10.1002/ejoc.201501197. - DOI
    1. Keijer T, Bakker V, Slootweg J C. Nat Chem. 2019;11:190–195. doi: 10.1038/s41557-019-0226-9. - DOI - PubMed
    1. Perna F M, Vitale P, Capriati V. Curr Opin Green Sustainable Chem. 2020;21:27–33. doi: 10.1016/j.cogsc.2019.09.004. - DOI
    1. Ramón D J, Guillena G, editors. Deep Eutectic Solvents: Synthesis, Properties, and Applications. 1st ed. Weinheim, Germany: Wiley-VCH; 2019. - DOI