Efficient production of amino-, azo- and azoxy- aromatics is important in chemical industries. In this manuscript, we reported that controllable chemoselective hydrogenation of nitrobenzene to produce aniline, azoxybenzene and azobenzene was realized over CQDs/ZnIn₂S₄ nanocomposite under visible light via simply regulating the reaction medium including the alkalinity and the hydrogen source. An optimized production of aniline was obtained over 3.0 wt% CQDs/ZnIn₂S₄ nanocomposite in a reaction medium of TEOA: MeOH (1:1), while a strong alkaline reaction medium promote N-N coupling to produce azoxybenzene and azobenzene. In addition, azoxybenzne is the intermediate to form azobenzene during the hydrogenation of nitrobenzene, in which a strong hydrogen source like TEOA is indispensable for the transformation. This study not only demonstrated a noble metal-free photocatalytic system for visible light induced efficient and controllable chemoselective hydrogenation of nitrobenzene to produce aniline, azobenzene and azoxybenzene, but also highlights the great potential of photocatalysis in organic syntheses.

氨基，偶氮和azo氧基芳族化合物的有效生产在化学工业中很重要。在此手稿中，我们报道了在CQDs / ZnIn ₂ S ₄纳米复合材料上可见光下，通过简单地调节包括碱度和氢源在内的反应介质，就实现了可控的硝基苯的化学选择性加氢，以生成苯胺，a氧基苯和偶氮苯。在3.0 wt％CQDs / ZnIn ₂ S _4上获得了优化的苯胺生产纳米复合物在TEOA：MeOH（1：1）的反应介质中，而强碱性反应介质会促进NN偶联，从而生成a氧基苯和偶氮苯。另外，a氧基苯是硝基苯加氢过程中形成偶氮苯的中间体，其中强氢源（如TEOA）对于转化是必不可少的。这项研究不仅证明了一种无贵金属的光催化体系，可用于可见光诱导硝基苯的高效可控化学选择性加氢，以生产苯胺，偶氮苯和a氧基苯，而且还强调了光催化在有机合成中的巨大潜力。