Palladium Nanoparticle-Catalyzed Stereoselective Domino Synthesis of All-Carbon Tetrasubstituted Olefin Containing Oxindoles via Carbopalladation/C–H Activation

The binaphthyl stabilized palladium nanoparticles (Pd-BNP) catalyzed single-step, stereoselective domino synthesis of symmetrically and unsymmetrically all-carbon tetrasubstituted olefin containing oxindoles from readily accessible anilides has been developed. The Pd-BNP catalyst showed a wide range of functional group tolerance that enabled building a library of heteroaromatics. This reusable Pd catalyst reflected its utility in the synthesis of biologically important AMP-activated protein kinase deprived of any metal Pd contamination. The nanocatalyst was easily recovered and reused five times without any appreciable loss in particle size or catalytic activity.本研究开发了以联萘稳定钯纳米颗粒（Pd-BNP）为催化剂，由易得的酰苯胺类化合物出发，经一步立体选择性多米诺反应合成含全碳四取代烯烃的对称与非对称羟吲哚类化合物的方法。该Pd-BNP催化剂具备广泛的官能团兼容性，可用于构建杂芳化合物库。这种可回收钯催化剂在合成无金属钯污染的、具有重要生物活性的AMP活化蛋白激酶（AMP-activated protein kinase）相关化合物中彰显了其应用价值。该纳米催化剂易于回收，可重复使用五次，且其粒径与催化活性无明显衰减。