Catalytic Reductions and Tandem Reactions of Nitro Compounds Using in Situ Prepared Nickel Boride Catalyst in Nanocellulose Solution

Kaniraj Jeya Prathap; Qiong Wu; Richard T Olsson; Peter Dinér

doi:10.1021/acs.orglett.7b02090

Catalytic Reductions and Tandem Reactions of Nitro Compounds Using in Situ Prepared Nickel Boride Catalyst in Nanocellulose Solution

Org Lett. 2017 Sep 15;19(18):4746-4749. doi: 10.1021/acs.orglett.7b02090. Epub 2017 Aug 31.

Authors

Kaniraj Jeya Prathap¹, Qiong Wu², Richard T Olsson², Peter Dinér¹

Affiliations

¹ Department of Chemistry, Organic Chemistry, KTH Royal Institute of Technology , Teknikringen 30, 10044 Stockholm, Sweden.
² Department of Fiber and Polymer Technology, Polymeric Materials, KTH Royal Institute of Technology , Teknikringen 58, 10044 Stockholm, Sweden.

PMID: 28858520
DOI: 10.1021/acs.orglett.7b02090

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't