Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, Tamil Nadu, India.
J Org Chem. 2020 Apr 3;85(7):4682-4694. doi: 10.1021/acs.joc.9b03397. Epub 2020 Mar 25.
A single-step, stereoselective protocol for the synthesis of unsymmetrically substituted ()-3-allylideneoxindole and ()-3-allylidenebenzofuran from readily accessible starting materials using palladium binaphthyl nanoparticles (Pd-BNPs) has been developed. Pd-BNP showing a wide range of functional group tolerance and an immense array of substrate scope have been explored with the successful synthesis of the drug molecule "tubulin polymerization inhibitor" free from trace metal impurities. The model reaction is extended to a gram-scale synthesis, and one of the products is utilized for derivatization. The Pd-BNP has been recycled up to 5 catalytic cycles without any loss in reaction yields and particle size of nanoparticles.
已开发出一种从易得起始原料出发，通过钯联萘纳米粒子（Pd-BNPs），单步、立体选择性合成不对称取代的（）-3-亚烯丙基氧吲哚和（）-3-亚烯丙基苯并呋喃的方法。Pd-BNP 显示出广泛的官能团耐受性和底物范围，成功合成了无痕量金属杂质的药物分子“微管蛋白聚合抑制剂”。该模型反应扩展到克级规模的合成，其中一个产物用于衍生化。Pd-BNP 已被回收 5 个催化循环，反应产率和纳米粒子的粒径没有任何损失。
