Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Author:

Dinér Peter1,Proietti Giampiero1,Prathap Kaniraj Jeya1,Ye Xinchen2,Olsson Richard T.2

Affiliation:

1. Division of Organic Chemistry, Department of Chemistry, School of Engineering Sciences in Chemistry, Biology and Health, KTH – Royal Institute of Technology

2. Department Fiber and Polymer Technology, School of Engineering Sciences in Chemistry, Biotechnology and Health, KTH – Royal Institute of Technology

Abstract

AbstractNickel 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.

Funder

KTH Royal institute of Technology

Wenner-Gren Stiftelserna

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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