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一种基于一锅法连续氮杂迈克尔加成和光催化铜催化的叠氮-炔环加成点击反应的新合成途径。

A new synthetic pathway based on one-pot sequential aza-Michael addition and photoCuAAC click reactions.

作者信息

Yin Boyang, Croutxé-Barghorn Céline, Delaite Christelle, Allonas Xavier

机构信息

Laboratory of Macromolecular Photochemistry and Engineering, University of Haute-Alsace 3 rue Alfred Werner 68093 Mulhouse Cedex France

出版信息

RSC Adv. 2019 Feb 7;9(9):4824-4831. doi: 10.1039/c8ra10011j. eCollection 2019 Feb 5.

DOI:10.1039/c8ra10011j
PMID:35514625
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9060615/
Abstract

A solvent-free process is described for the synthesis of tailor-made molecules from a one-pot, two-step approach combining aza-Michael addition and photoinduced copper(i) catalysed azide-alkyne (photo-CuAAC) reactions. After the first reaction between an amine and an acrylate, cycloaddition between an azide and an alkyne is activated by light irradiation in the presence of a copper complex. The kinetics of the aza-Michael addition and photo-CuAAC reaction were investigated by liquid state H NMR spectroscopy and real-time Fourier transform infrared spectroscopy. This new process represents a well-defined spatio-temporal pathway to the synthesis of bespoke intermediate molecules for various applications.

摘要

描述了一种无溶剂方法，该方法采用一锅两步法合成定制分子，该方法结合了氮杂迈克尔加成反应和光诱导铜（I）催化的叠氮化物-炔烃环加成反应（光催化铜催化的点击化学反应）。在胺与丙烯酸酯之间的第一步反应之后，在铜配合物存在下通过光照射激活叠氮化物与炔烃之间的环加成反应。通过液态核磁共振光谱和实时傅里叶变换红外光谱研究了氮杂迈克尔加成反应和光催化铜催化的点击化学反应的动力学。这种新方法代表了一种明确的时空途径，可用于合成各种应用的定制中间体分子。

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2
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Polym Chem. 2017 Jun 28;8(24):3668-3673. doi: 10.1039/C7PY00623C. Epub 2017 May 8.
3
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Polym Chem. 2016 Jan 21;7(3):603-612. doi: 10.1039/c5py01655j. Epub 2015 Nov 18.
4
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Eur J Med Chem. 2014 Sep 12;84:433-43. doi: 10.1016/j.ejmech.2014.07.042. Epub 2014 Jul 14.
5
Direct observation of reduction of Cu(II) to Cu(I) by terminal alkynes.直接观察末端炔烃将 Cu(II)还原为 Cu(I)。
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6
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