Tetrahedron 2018-03-10

Cu-catalyzed reduction of azaarenes and itroaromatics with diboronic acid as reductant

Danwei Pi, Haifeng Zhou, Yanmei Zhou, Qixing Liu, Renke He, Guanshuo Shen, Yasuhiro Uozumi

Index: 10.1016/j.tet.2018.03.014

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Abstract

A ligand-free copper-catalyzed reduction of azaarenes with diboronic acid as reductant in an aprotic solvent under mild conditions has been developed. Most interestingly, the nitroazaarenes could be reduced exclusively to give the corresponding amines without touching the azaarene moieties. Furthermore, the reductive amination of aromatic nitro compounds and aromatic aldehydes has also been realized. A series of hydrogenated azaarenes and secondary amines were obtained with good functional group tolerance.