Department of Chemistry, Organic Chemistry, KTH Royal Institute of Technology , Teknikringen 30, 10044 Stockholm, Sweden.
Department of Fiber and Polymer Technology, Polymeric Materials, KTH Royal Institute of Technology , Teknikringen 58, 10044 Stockholm, Sweden.
Org Lett. 2017 Sep 15;19(18):4746-4749. doi: 10.1021/acs.orglett.7b02090. Epub 2017 Aug 31.
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 % NiCl). 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.
描述了一种温和、高效的方法，即在 TEMPO 氧化纳米纤维素在水中（0.01wt%）的溶液中，使用氯化镍/硼氢化钠原位还原硝基芳烃和脂肪族硝基化合物为胺，产率优异。纳米纤维素对催化剂具有稳定作用，提高了催化剂的周转数，并能够降低镍催化剂的负载量（0.1-0.25mol%NiCl）。此外，还开发了两种串联方案，其中原位形成的胺被 Boc 保护成氨基甲酸酯，或者进一步与环氧化物反应，以优异的产率生成β-氨基醇。
