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Catalytic Reductions and Tandem Reactions of Nitro Compounds Using in Situ Prepared Nickel Boride Catalyst in Nanocellulose Solution
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.ORCID iD: 0000-0001-6782-6622
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2017 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 18, p. 4746-4749Article in journal (Refereed) Published
Abstract [en]

A mild and efficient method for the in situ reduction of a wide range of nitroarenes and aliphatic nitrocompounds to amines in excellent yields using nickel chloride/sodium borohydride in a solution of TEMPO-oxidized nanocellulose in water (0.01 wt %) is described. The nanocellulose has a stabilizing effect on the catalyst, which increases the turnover number and enables low loading of nickel catalyst (0.1-0.25 mol % NiCl2). In addition, two tandem protocols were developed in which the in situ formed amines were either Boc-protected to carbamates or further reacted with an epoxide to yield β-amino alcohols in excellent yields.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2017. Vol. 19, no 18, p. 4746-4749
Keywords [en]
Ray Photoelectron-Spectroscopy, Metal Salt Systems, Ni-B Catalyst, Sodium-Borohydride, Selective Reduction, Cellulose Nanocrystals, Hydrogenation Catalyst, Chemoselective Hydrogenation, Gold Nanoparticles, Palladium Nanoparticles
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-213499DOI: 10.1021/acs.orglett.7b02090ISI: 000411304300011PubMedID: 28858520Scopus ID: 2-s2.0-85029508011OAI: oai:DiVA.org:kth-213499DiVA, id: diva2:1147651
Funder
Wenner-Gren Foundations, UPD2016-0084
Note

QC 20171011

Available from: 2017-10-06 Created: 2017-10-06 Last updated: 2017-10-16Bibliographically approved

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