Amphiphilic self-assembled polymeric copper catalyst to parts per million levels: click chemistry

Journal of the American Chemical Society
Yoichi M A YamadaYasuhiro Uozumi

Abstract

Self-assembly of copper sulfate and a poly(imidazole-acrylamide) amphiphile provided a highly active, reusable, globular, solid-phase catalyst for click chemistry. The self-assembled polymeric Cu catalyst was readily prepared from poly(N-isopropylacrylamide-co-N-vinylimidazole) and CuSO(4) via coordinative convolution. The surface of the catalyst was covered with globular particles tens of nanometers in diameter, and those sheetlike composites were layered to build an aggregated structure. Moreover, the imidazole units in the polymeric ligand coordinate to CuSO(4) to give a self-assembled, layered, polymeric copper complex. The insoluble amphiphilic polymeric imidazole Cu catalyst with even 4.5-45 mol ppm drove the Huisgen 1,3-dipolar cycloaddition of a variety of alkynes and organic azides, including the three-component cyclization of a variety of alkynes, organic halides, and sodium azide. The catalytic turnover number and frequency were up to 209000 and 6740 h(-1), respectively. The catalyst was readily reused without loss of catalytic activity to give the corresponding triazoles quantitatively.

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Citations

Oct 13, 2015·Bioconjugate Chemistry·Mohammad Aref KhalilyMustafa O Guler
Aug 17, 2016·Journal of the American Chemical Society·Yugang BaiSteven C Zimmerman
Sep 9, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alessandro Mandoli
Sep 14, 2016·Scientific Reports·Debkumar NandiKaushik Mallick
May 31, 2014·Scientific Reports·Haiqiang WuBen Zhong Tang
Mar 2, 2018·Chemical Communications : Chem Comm·R HudsonY Uozumi
Apr 7, 2018·Chemical Biology & Drug Design·Saleha BanuDivyasphoorthi Vardhan
Aug 19, 2015·Organic & Biomolecular Chemistry·Estela HaldónPedro J Pérez
Sep 29, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hong ChiJoshy K S
Apr 29, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Firdaus Rahaman GayenBiswajit Saha
Jul 31, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Thibault Cheisson, Audrey Auffrant
Oct 7, 2015·Chemistry : a European Journal·Yoichi M A YamadaYasuhiro Uozumi
Jul 3, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Shi-Qiang BaiT S Andy Hor
Aug 6, 2014·Journal of the American Chemical Society·Christophe DeraedtDidier Astruc
Nov 8, 2018·Organic Letters·Wen-Long LeiQiang Liu

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