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在水中使用热响应性聚合物胶束的钯催化 Mizoroki-Heck 反应和无铜 Sonogashira 偶联反应

Palladium-Catalyzed Mizoroki-Heck and Copper-Free Sonogashira Coupling Reactions in Water Using Thermoresponsive Polymer Micelles.

作者信息

Suzuki Noriyuki, Koyama Shun, Koike Rina, Ebara Nozomu, Arai Rikito, Takeoka Yuko, Rikukawa Masahiro, Tsai Fu-Yu

机构信息

Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioi-cho, Chiyoda-ku, Tokyo 102-8554, Japan.

Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 10608, Taiwan.

出版信息

Polymers (Basel). 2021 Aug 13;13(16):2717. doi: 10.3390/polym13162717.

Abstract

A few kinds of thermoresponsive diblock copolymers have been synthesized and utilized for palladium-catalyzed coupling reactions in water. Poly(-isopropylacrylamide) (PNIPAAm) and poly(,-diethylacrylamide) (PDEAAm) are employed for thermoresponsive segments and poly(sodium 4-styrenesulfonate) (PSSNa) and poly(sodium 2-acrylamido-methylpropanesulfonate) (PAMPSNa) are employed for hydrophilic segments. Palladium-catalyzed Mizoroki-Heck reactions are performed in water and the efficiency of the extraction process is studied. More efficient extraction was observed for the PDEAAm copolymers when compared with the PNIPAAm copolymers and conventional surfactants. In the study of the Sonogashira coupling reactions in water, aggregative precipitation of the products was observed. Washing the precipitate with water gave the product with satisfactory purity with a good yield.

摘要

已经合成了几种热响应性二嵌段共聚物,并将其用于水中钯催化的偶联反应。聚(N-异丙基丙烯酰胺)(PNIPAAm)和聚(N,N-二乙基丙烯酰胺)(PDEAAm)用作热响应性链段,聚(4-苯乙烯磺酸钠)(PSSNa)和聚(2-丙烯酰胺基-2-甲基丙磺酸钠)(PAMPSNa)用作亲水性链段。在水中进行钯催化的 Mizoroki-Heck 反应,并研究了萃取过程的效率。与 PNIPAAm 共聚物和传统表面活性剂相比,PDEAAm 共聚物的萃取效率更高。在研究水中的 Sonogashira 偶联反应时,观察到产物的聚集沉淀。用水洗涤沉淀物得到纯度令人满意且产率良好的产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f693/8402173/da8195e7e33e/polymers-13-02717-g001.jpg

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