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Polarclean作为用于杂环化合物最小化废弃物合成的可持续反应介质。

Polarclean as a Sustainable Reaction Medium for the Waste Minimized Synthesis of Heterocyclic Compounds.

作者信息

Ferlin Francesco, Luciani Lorenzo, Viteritti Orlando, Brunori Francesco, Piermatti Oriana, Santoro Stefano, Vaccaro Luigi

机构信息

Laboratory of Green Synthetic Organic Chemistry, Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Perugia, Italy.

出版信息

Front Chem. 2019 Jan 29;6:659. doi: 10.3389/fchem.2018.00659. eCollection 2018.

Abstract

Herein we report the use of Rhodiasolv Polarclean as a novel polar aprotic solvent for the synthesis of decorated heterocycles via dipolar cycloaddition (isooxazoles) or intramolecular C-H functionalization processes (benzo-fused chromenes). The use of Polarclean allowed to isolate the final products in good yields by simple solid filtration or liquid-liquid phase separation, avoiding the need for chromatographic purification. Moreover, since in the synthesis of benzo-fused chromenes, the metal catalyst is retained in Polarclean, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without any apparent loss in efficiency. This methodology is associated with a limited waste production. These results extend the applicability of Polarclean as a promising reaction medium for the replacement of toxic petrol-based solvent.

摘要

在此,我们报道了使用罗地亚溶剂Polarclean作为一种新型极性非质子溶剂,通过偶极环加成反应(异恶唑)或分子内C-H官能化过程(苯并稠合色烯)来合成修饰的杂环化合物。使用Polarclean能够通过简单的固体过滤或液-液相分离以良好的产率分离出最终产物,无需进行色谱纯化。此外,由于在苯并稠合色烯的合成中,金属催化剂保留在Polarclean中,催化剂/反应介质可以很容易地重复用于连续的反应运行,而效率没有任何明显损失。这种方法产生的废物有限。这些结果扩展了Polarclean作为一种有前景的反应介质用于替代有毒的石油基溶剂的适用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db80/6362304/d12752bfc57a/fchem-06-00659-g0001.jpg

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