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Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters
Green Chemistry ( IF 9.3 ) Pub Date : 2020/01/15 , DOI: 10.1039/c9gc03957k Ziqiang Yan 1, 2, 3, 4, 5 , Xiaoyu Xie 1, 2, 3, 4, 5 , Qun Song 1, 2, 3, 4, 5 , Fulei Ma 1, 2, 3, 4, 5 , Xinyu Sui 1, 2, 3, 4, 5 , Ziyu Huo 1, 2, 3, 4, 5 , Mingming Ma 1, 2, 3, 4, 5
Green Chemistry ( IF 9.3 ) Pub Date : 2020/01/15 , DOI: 10.1039/c9gc03957k Ziqiang Yan 1, 2, 3, 4, 5 , Xiaoyu Xie 1, 2, 3, 4, 5 , Qun Song 1, 2, 3, 4, 5 , Fulei Ma 1, 2, 3, 4, 5 , Xinyu Sui 1, 2, 3, 4, 5 , Ziyu Huo 1, 2, 3, 4, 5 , Mingming Ma 1, 2, 3, 4, 5
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We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution under ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo-compounds. The catalyst is in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3 ± 0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1–0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates and offers a green and sustainable method for the rapid and large-scale production of valuable N-containing chemicals.
中文翻译：
钯纳米簇催化串联选择性还原硝基芳烃
我们报道了在环境条件下，硼氢化钠（NaBH 4）在水溶液中可催化串联还原硝基芳烃，它可以选择性地产生五类含氮化合物：苯胺，N-芳基羟胺，z氧基-，偶氮和-化合物。催化剂是通过NaBH 4还原Pd（OAc）2而原位生成的超小型钯纳米簇（Pd NCs，直径为1.3±0.3 nm）。这些高活性的Pd NCs通过表面配位的硝基芳烃得以稳定，这抑制了Pd NCs的进一步生长和聚集。通过控制Pd（OAc）2（0.1-0.5 mol％的亚硝基芳烃）和NaBH 4的浓度，水/乙醇溶剂比和串联反应顺序，可以在室温下不到30分钟内以优异的收率（最高98％）获得五类含氮化合物。这种可调谐的催化串联反应可在广泛的硝基芳烃底物上高效运行，并为快速，大规模生产有价值的含氮化学品提供了一种绿色，可持续的方法。
更新日期：2020-02-24
中文翻译：
钯纳米簇催化串联选择性还原硝基芳烃
我们报道了在环境条件下，硼氢化钠（NaBH 4）在水溶液中可催化串联还原硝基芳烃，它可以选择性地产生五类含氮化合物：苯胺，N-芳基羟胺，z氧基-，偶氮和-化合物。催化剂是通过NaBH 4还原Pd（OAc）2而原位生成的超小型钯纳米簇（Pd NCs，直径为1.3±0.3 nm）。这些高活性的Pd NCs通过表面配位的硝基芳烃得以稳定，这抑制了Pd NCs的进一步生长和聚集。通过控制Pd（OAc）2（0.1-0.5 mol％的亚硝基芳烃）和NaBH 4的浓度，水/乙醇溶剂比和串联反应顺序，可以在室温下不到30分钟内以优异的收率（最高98％）获得五类含氮化合物。这种可调谐的催化串联反应可在广泛的硝基芳烃底物上高效运行，并为快速，大规模生产有价值的含氮化学品提供了一种绿色，可持续的方法。
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