Efficient chemoselective hydrogenation of organic azides catalyzed by palladium nanoparticles with alkyne-derived homogeneous supports

TETRAHEDRON LETTERS

卷:57

Article

Ohkuma, Takeshi¹ 

[1] Hokkaido Univ, Fac Engn, Div Appl Chem, Sapporo, Hokkaido 0608628, Japan

关键词: Palladium;    Nanoparticles;    Hydrogenation;    Organic azide;    Chemoselective;   

DOI  :  10.1016/j.tetlet.2016.08.002

来源: Elsevier

【 摘 要 】

Catalytic chemoselective hydrogenation of organic azides using palladium nanoparticles stabilized by alkyne derivatives was studied. A broad range of aromatic and aliphatic azides were smoothly reduced to the corresponding amines in excellent yields with a quite small amount of the catalyst. Hydrogenation of 3-phenylpropylazide gave 3-phenylpropylamine almost quantitatively with a substrate-to-palladium molar ratio (S/Pd) of 12,900 under 8 atm of H-2. The reaction under 1 atm of H2 also proceeded smoothly with an S/Pd of 1000. Several reduction-sensitive functional groups, such as carbonyl, halide, benzylic OH, and aliphatic nitro were well tolerated under the reaction conditions. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

Free