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CC BY 4.0 · Synthesis 2022; 54(01): 133-146
DOI: 10.1055/a-1579-2190
DOI: 10.1055/a-1579-2190
feature
Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions
K.J.P., G.P. and P.D. thank the Wenner-Gren Stiftelserna (Grant No. UPD2016-0084) and KTH Royal institute of Technology for financial support.
Abstract
Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.
Key words
Ni-B - nickel boride - nitro reduction - azide reduction - nickel boride catalyzed hydrogenation - TEMPO nanocellulose - crystalline nanocelluloseSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1579-2190.
- Supporting Information
Publication History
Received: 08 June 2021
Accepted after revision: 05 August 2021
Accepted Manuscript online:
05 August 2021
Article published online:
20 October 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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