Hong Jee Eun, Jung Yeonghun, Park Youmie, Park Yohan
College of Pharmacy and Inje Institute of Pharmaceutical Sciences and Research, Inje University, 197 Inje-ro, Gimhae, Gyeongnam 50834, Republic of Korea.
ACS Omega. 2020 Mar 27;5(13):7576-7583. doi: 10.1021/acsomega.0c00402. eCollection 2020 Apr 7.
A selective synthesis of hydrazoarene from nitroarene and its application are reported. Using polystyrene (PS) resins as solid supports for Au nanoparticles (AuNPs), polystyrene-supported Au nanoparticles (AuNPs@PS) were synthesized and characterized. In the presence of AuNPs@PS (1.0 mol %) as a catalyst, nitroarenes afforded corresponding hydrazoarenes (up to 99%) with high selectivity (up to 100%) under mild reaction conditions (NaBH, 50% aq. EtOH, and room temperature). Depending on the reaction conditions (the amount of NaBH, the substituent of nitroarenes, and the sequential addition of HCl), nitroarenes were converted to corresponding azoarenes (up to 95%), aminoarenes (up to 99%), and 4,4'-diaminobiaryls (up to 99%). Our easily recyclable catalytic system using a solid-phase reaction vessel provides an attractive synthetic method in an eco-friendly and sustainable manner.
报道了一种由硝基芳烃选择性合成氢化偶氮芳烃及其应用。以聚苯乙烯（PS）树脂为金纳米颗粒（AuNPs）的固体载体，合成并表征了聚苯乙烯负载的金纳米颗粒（AuNPs@PS）。在作为催化剂的AuNPs@PS（1.0 mol%）存在下，硝基芳烃在温和的反应条件下（NaBH、50%乙醇水溶液和室温）以高选择性（高达100%）得到相应的氢化偶氮芳烃（高达99%）。根据反应条件（NaBH的量、硝基芳烃的取代基以及HCl的顺序添加），硝基芳烃可转化为相应的偶氮芳烃（高达95%）、氨基芳烃（高达99%）和4,4'-二氨基联芳基（高达99%）。我们使用固相反应容器的易于回收的催化体系以生态友好和可持续的方式提供了一种有吸引力的合成方法。
