Palladium Nanoparticle-Catalyzed Stereoselective Domino Synthesis of 3-Allylidene-2(3H)-oxindoles and 3-Allylidene-2(3H)-benzofuranones,The Journal of Organic Chemistry

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Palladium Nanoparticle-Catalyzed Stereoselective Domino Synthesis of 3-Allylidene-2(3H)-oxindoles and 3-Allylidene-2(3H)-benzofuranones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-25 , DOI: 10.1021/acs.joc.9b03397
Naziya Parveen ₁ , Govindasamy Sekar ₁

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A single-step, stereoselective protocol for the synthesis of unsymmetrically substituted (E)-3-allylideneoxindole and (E)-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.

中文翻译：

钯纳米粒子催化的3-亚烷基-2（3 H）-羟吲哚和3-亚烷基-2（3 H）-苯并呋喃酮的立体选择性多米诺合成

已开发出一种单步立体选择性方案，可使用钯双萘基纳米粒子（Pd-BNPs）从易于获得的起始原料合成不对称取代的（E）-3-烯叉异吲哚和（E）-3-烯丙基苯并呋喃。通过成功合成不含痕量金属杂质的药物分子“微管蛋白聚合抑制剂”，已探索出显示出广泛的官能团耐受性和大量底物范围的Pd-BNP。模型反应扩展到克级合成，并且其中一种产物用于衍生化。Pd-BNP可以循环使用多达5个催化循环，而不会降低反应收率和纳米颗粒的粒径。

更新日期：2020-03-26

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